Memorial Day, observed on the last Monday of May in the United States, is not a public holiday in Anguilla. However, the island often welcomes American visitors during this time, and local establishments may host special events or promotions to cater to them. Given the proximity of Anguilla Day to Memorial Day weekend in 2025, visitors during this period can enjoy a blend of local celebrations and cultural experiences. It’s advisable to check with local venues and the Anguilla Tourist Board for specific events and activities in Anguilla planned during your stay.
Memorial Day in Anguilla: Sun, Sand & Unforgettable Moments
Memorial Day is all about remembering, reflecting, and taking a well-deserved break. If you’re dreaming of soft white sand, turquoise waters, and the perfect mix of adventure and relaxation, Anguilla is calling your name. This little slice of Caribbean paradise has everything you need for an epic long weekend getaway, from jaw-dropping beaches to incredible food and laid-back island vibes.
And here’s the best part, your trip isn’t complete without the perfect place to stay. That’s where The Fountain Anguilla comes in. Tucked away on the world-famous Shoal Bay, it’s the kind of place where you feel like you’ve truly escaped. So, let’s dive into the best ways to make the most of your Memorial Day weekend in Anguilla!
Start with Shoal Bay—Because, Obviously
If you’ve seen pictures of Anguilla, chances are you’ve seen Shoal Bay. It’s the kind of beach that looks like a desktop screensaver, but better in real life. Think soft sand, ridiculously blue water, and a vibe that’s all about taking it slow.
Grab a lounge chair, order a rum punch from a beach bar, and let the island do its thing. Want a little more action? Snorkeling here is amazing, with colorful fish darting through the reefs just a few feet from shore. And when you’re ready to wind down, your cozy retreat at The Fountain Anguilla is just a short stroll away.
Chase the Sunset on a Boat
A Memorial Day weekend in Anguilla isn’t complete without a sunset cruise. Picture yourself on a sleek catamaran, a glass of champagne in hand, watching the unobstructed view of the sunset. Sounds dreamy, right? Tradition Sailing offers unforgettable sunset sails where you can toast to the good life while gliding across the Caribbean Sea. It’s the kind of experience that sticks with you long after your vacation ends.
Snorkel, Dive, and Explore the Deep Blue
If you love the ocean, Anguilla’s got plenty of ways to get up close and personal with it. Head to Little Bay, a hidden gem only accessible by boat or kayak. The snorkeling here? Unreal. Crystal-clear water, tons of fish, and a peaceful cove that feels like your own private paradise.
Hop Over to a Tiny Island for the Day
Why stick to one island when you can explore a few? Anguilla is surrounded by little cays that feel like secret hideaways. Sandy Island and Prickly Pear Cays are a must-visit! Imagine uninhabited islands with nothing but a beach bar, freshly grilled lobster, and swaying palm trees.
Eat Like an Islander
Food in Anguilla? Next level. From casual beach BBQs to five-star dining, your taste buds are in for a treat. For a chill, toes-in-the-sand vibe, The Sunshine Shack serves up the juiciest grilled snapper and ribs, with reggae beats in the background. If you’re craving something a bit fancier, Blanchards offers a fusion of Caribbean flavors in an elegant beachfront setting. Either way, you can’t go wrong.
Treat Yourself to Some Island R&R
Vacations should be about relaxation too, right? Start your day with a morning yoga session by the ocean, or book a massage at Zemi – Thai House Spa, trust me, you won’t regret it. And if you’re staying at The Fountain Anguilla, you don’t even have to leave your suite to enjoy some serious relaxation. Just lounge by the pool, sip a cocktail, and let island time take over.
Local Events Around Memorial Day Weekend
While there are no major island-wide celebrations specifically tied to Memorial Day, the period does coincide with some notable events:
Anguilla Regatta: This three-day event, celebrating the island’s national sport of boat racing, typically takes place in May. While exact dates for 2025 haven’t been confirmed, it often aligns closely with Memorial Day weekend.
Anguilla Day: Celebrated annually on May 30th, Anguilla Day marks the island’s independence from St. Kitts and Nevis in 1967. Festivities include a highly anticipated sailboat race around the island, starting and ending at Sandy Ground, accompanied by live music and local cuisine.
Why Stay at The Fountain Anguilla?
At the end of a sun-soaked day, you’ll want a place that feels like home, only better. That’s The Fountain Anguilla. On Shoal Bay, it offers spacious two-bedroom Anguilla luxury rentals, modern amenities, and a peaceful atmosphere that’s perfect for unwinding. This boutique escape is your personal slice of paradise.
Make Memorial Day One to Remember
If you’re looking for an unforgettable way to spend Memorial Day, Anguilla is where it’s at. From breathtaking beaches to world-class dining, live music, and island adventures, there’s no better place to relax, recharge, and celebrate life.
So, what are you waiting for? Pack your bags, book an Anguilla vacation rental at The Fountain Anguilla, and get ready for the ultimate Memorial Day weekend in paradise.
Anguilla, a sun-kissed paradise in the Caribbean, is famed for its dazzling white-sand beaches and ultra-luxurious resorts. While the pristine shores of Shoal Bay East and the opulent tranquility of The Fountain Anguilla draw visitors from all over the world, this enchanting island has far more to offer than just its postcard-perfect coastline. For those willing to step off the well-trodden path, Anguilla hides a treasure trove of underappreciated sights, cultural wonders, and natural marvels waiting to be explored.
In this Anguilla attractions guide, we’ll take you beyond the obvious, diving into the lesser-known yet equally mesmerizing corners of Anguilla. From ancient petroglyphs and hidden beaches to vibrant fishing villages and offshore cays, you’ll discover the soul of Anguilla, one adventure at a time. In this blog you will get pro-tips and, of course, we’ll let you know how far each spot is from the luxurious comfort of The Fountain Anguilla, ensuring you can plan your days with ease.
Fountain Cavern National Park
Just a stone’s throw away, a quick 5-minute drive or a 20-minute walk from The Fountain Anguilla lies one of the island’s most awe-inspiring natural wonders: the Fountain Cavern National Park.
This mystical underground cave, featuring a freshwater pool and sacred petroglyphs, is an archaeological goldmine and a testament to the island’s indigenous past. The petroglyphs, believed to be carved by the island’s original Arawak inhabitants, depict spiritual symbols and figures that offer a glimpse into their ancient world. But, because access to the cave is restricted to protect its integrity, you will need to arrange a guided tour in advance through the Anguilla National Trust.
As one of the most important pre-Columbian sites in the Caribbean, the historical significance and natural beauty of the site make it a must-visit. It’s a rare opportunity to connect with the spiritual and cultural legacy of Anguilla’s earliest people.
Island Harbour Village
If you’re looking to experience Anguilla beyond its luxury resorts, head to Island Harbour, a charming fishing village on the island’s northeastern coast. Here, colorful wooden boats bob gently in the turquoise waters, and local fishermen haul in the day’s freshest catch. This lively coastal spot is also home to the beloved Festival Del Mar, an annual celebration of the island’s maritime heritage, featuring boat races, seafood feasts, and live music. Located about 3 miles (4.8 km) east, a breezy 7-minute drive from The Fountain, Island Harbour is best reached by car.
You can also stop by Scilly Cay, a nearby islet known for its lobster lunches and rum punches, accessible by a quick boat ride from the village. Combine your visit with a swim or snorkel in the crystal-clear waters.
Visiting Island Harbour is a chance to interact with friendly locals and experience authentic island life and the perfect spot to snap stunning photos of the traditional fishing boats. The laid-back atmosphere and authentic vibe make it a refreshing contrast to the island’s more polished tourist areas.
Scilly Cay
Scilly Cay is a tiny, uninhabited islet except for the legendary beach bar and restaurant that calls it home. Imagine stepping onto a tiny, sun-drenched island where the scent of grilled lobster fills the air, a reggae tune drifts lazily from a nearby speaker, and the turquoise sea stretches endlessly in every direction. Welcome to Scilly Cay, Anguilla’s best-kept secret and an absolute must-visit for those looking to experience an authentic, laid-back Caribbean paradise.
If you’re staying at The Fountain Anguilla, this magical little cay is just a short adventure away offering some of the freshest seafood and strongest rum punches. And getting there is super easy! Just a 7-minute drive to Island Harbour, then a 2-minute boat ride makes it a perfect half-day or full-day trip.
The crystal-clear waters surrounding Scilly Cay are perfect for a refreshing dip. Since the island is protected by a natural reef, the water remains calm, making it an ideal spot for both swimming and snorkeling. This is a cash-only establishment though, and credit cards are not accepted, so be sure to walk with cash.
Scilly Cay is the definition of a Caribbean dream; an intimate, picturesque island where time slows down, the seafood melts in your mouth, and the rum flows freely. So, if you’re staying at The Fountain Anguilla, grab your swimsuit, head to Island Harbour, and set sail for Scilly Cay to your own private slice of paradise.
Savannah Bay
Keeping it relatively close, just 4 miles (6.4 km) southeast, about a 10-minute drive, we suggest you visit this other special place called Savannah Bay. Anguilla has no shortage of breathtaking beaches, but Savannah Bay remains a hidden jewel. Away from the tourist crowds, this vast stretch of powdery sand and crystal-clear waters is the definition of tranquility. It’s the kind of place where you can lay out a towel, listen to the gentle waves, and feel like you have the entire beach to yourself.
You undoubtedly will want to spend some time. It’s secluded and peaceful, perfect for a private beach day. It’s ideal for swimming, sunbathing, or simply unwinding with a good book. A great alternative to busier beaches like Shoal Bay.
Crocus Bay and Katouche Bay Hiking Trail
While the beaches of Crocus Bay are well-known for their tranquility, few visitors explore the rugged hiking trails that lead to Katouche Bay, often referred to as the “Valley of the Cave.” This hiking trail is a perfect mix of beach, jungle, and cave exploration, great for adventurers looking to add some hiking to their itinerary and a chance to spot rare island wildlife.
The trail rewards adventurers with lush vegetation, fascinating rock formations, and a sense of solitude rarely found on the island. Katouche Bay is also home to caves that are believed to have been inhabited by Anguilla’s earliest settlers.
Crocus Bay is about a 10 to 15-minute drive from The Fountain Anguilla. Be sure to bring sturdy footwear, and water, and have a guide if you’re unfamiliar with the terrain. The trails can be challenging but are well worth the effort. A guided experience will also help you spot wildlife and learn about the island’s native flora. Whether you’re a nature enthusiast or simply seeking a unique experience, this hike offers both adventure and history.
Sandy Ground’s Heritage Trail
On the western end of the island, Sandy Ground is often seen as Anguilla’s social and cultural hub. It was once the capital of the island. While many flock here for beach bars and nightlife, few take the time to explore its rich history through the Sandy Ground Heritage Trail.
The trail offers a window into Anguilla’s salt production history, with remnants of salt ponds and a pump house. Local guides share stories of how the salt trade shaped the island’s economy in the 19th and early 20th centuries. Beyond its historical significance, the trail provides stunning views of the surrounding area, making it a feast for the eyes as well as the mind.
The Fountain Anguilla is located in Shoal Bay East, on the northeastern coast of Anguilla. Sandy Ground is centrally located and easily accessible by car or taxi. The distance between The Fountain Anguilla and Sandy Ground is approximately 10 kilometers (6.2 miles), which typically takes about 20 minutes to drive.
Visit in the early morning or late afternoon to avoid the midday sun, and don’t forget your camera for picturesque views of the salt ponds and nearby beaches.
Anguilla’s Salt Ponds
Anguilla may be best known for its powdery white beaches and turquoise waters, but the island has another fascinating natural feature that often goes unnoticed: its salt ponds. Once the backbone of Anguilla’s economy, these shimmering, sun-kissed lagoons hold a deep-rooted history, a thriving ecosystem, and an off-the-beaten-path charm that makes them a must-visit for nature lovers and history buffs alike.
If you’re staying at The Fountain Anguilla, taking a trip to the island’s salt ponds is an easy and rewarding excursion. Whether you’re a birdwatching enthusiast, a photography lover, or simply someone who enjoys exploring unique landscapes, Anguilla’s salt ponds offer a serene escape from the bustling beach scene.
Anguilla’s salt ponds are a haven for birdwatchers, providing an ideal habitat for a variety of bird species. Snowy egrets, herons, brown pelicans and Black-necked stilts are commonly spotted wading through the shallow waters, searching for food. The peaceful, undisturbed nature of these ponds makes them one of the best birdwatching spots in the Caribbean.
There are over 12 salt ponds scattered across Anguilla, each offering its own unique beauty and experience. Here are a few of the most notable ones:
Located in Sandy Ground, this is the most famous salt pond in Anguilla due to its historical importance. This pond is about 7 miles (15-minute drive) away from The Fountain and best for history, photography, birdwatching.
West End Pond is the largest salt pond in Anguilla and a prime spot for spotting flamingos. This pond is 12 miles (25-minute drive) away from The Fountain and best for birdwatching and nature walks.
One of the least-visited salt ponds, Long Pond in East End offers a serene escape for those looking to experience Anguilla’s quieter side. The pond is 5 miles (10-minute drive) away from The Foutain and ideal for solitude and scenic landscapes.
Anguilla’s salt ponds may not get as much attention as its beaches, but they offer an incredible opportunity to connect with the island’s history, wildlife, and raw beauty. For all the locations, it is best to visit during early morning or late afternoon when the light is golden, and the birds are most active. Be sure to bring binoculars and a camera with a zoom lens to capture stunning wildlife shots!
Anguilla’s Local Art Galleries
While Anguilla is celebrated for its natural beauty, its burgeoning art scene is equally compelling. Several local galleries showcase the island’s creative spirit. If you need a break from the sun and sand, stepping into a cool, tranquil gallery offers a refreshing change of pace. Many galleries also double as cultural hubs, where you can chat with artists, learn about the island’s history, and even catch a live demonstration.
Devonish Art Gallery & Cheddie’s Carving Studio
Both located in West End Village, the distance between these galleries from The Fountain Anguilla is 12 miles or 25-minute drive.
Run by talented sculptor Courtney Devonish, Devonish Art Gallery is a treasure trove of handcrafted pottery, wooden carvings, and intricate jewelry. Devonish’s sculptures, made from mahogany and other tropical woods, have a distinctive elegance, blending contemporary designs with traditional craftsmanship. Devonish often creates small, affordable sculptures that make perfect keepsakes or gifts. Also, if you’re lucky, you might catch him working on a new piece in his studio!
On the other hand, Cheddie Richardson, one of Anguilla’s most celebrated sculptors, transforms driftwood and other natural materials into stunning works of art. His sculptures, often inspired by marine life and island folklore, have gained international acclaim. The studio itself is an experience, with pieces ranging from delicate carvings to large statement sculptures that command attention. Each piece has a fascinating background, whether it’s inspired by a local legend or a moment from his childhood.
Many of the pieces are available for purchase, so consider taking home a unique keepsake. The artists are often present, allowing you to gain insight into their creative process.
Plan Your Trip to Anguilla Today
Anguilla is a sparkling gem, but beyond its sun-drenched beaches and luxurious resorts lies a world of hidden treasures just waiting to be uncovered. Whether you’re a thrill-seeking adventurer, a history lover with a curious spirit, a nature admirer craving untouched beauty, or an art enthusiast searching for inspiration, this island has something special in store for you. Wander through ancient caves whispering tales of the past, stroll along secret beaches where the only footprints are your own, or dive into the island’s vibrant culture in charming villages. So, next time you’re in Anguilla, book your Anguilla vacation rental at The Fountain Anguilla and go beyond the obvious, because you just might stumble upon the most magical moments of your trip! Reach out today and book our studio penthouse at The Fountain Anguilla today.
If there’s one thing Anguilla knows how to do aside from boasting some of the most breathtaking beaches in the Caribbean, it’s serving up incredible food. This tiny island may be small in size, but it’s bursting at the seams with culinary gems, from hidden beachfront shacks serving up just-caught seafood to elegant restaurants where you’ll be treated like royalty.
Whether you’re staying at Fountain Anguilla or just exploring the island, prepare your taste buds for an adventure. Below, we will share with you the top Anguilla dining picks in specific order, based on visitors’ reviews and requests. Let’s take a delicious journey through these unforgettable dining spots, each offering its own unique take on paradise-on-a-plate. Plus, we’ll make it easy for you to plan your visit with distances from The Fountain Anguilla so you can hop in your car and follow your cravings. Buckle up, food lovers, this is the ultimate guide to eating your way through Anguilla!
Madeariman Restaurant – Shoal Bay
If you’re looking for casual, toes-in-the-sand dining with bold Caribbean flavors, this is your spot. Madeariman is all about unfussy, delicious food with an unbeatable beachfront view. Situated directly on the pristine Shoal Bay East, literally 2-minute drive away from The Fountain, Madeariman offers a delightful beachfront dining experience. The menu boasts a variety of seafood dishes, including fresh lobster and fish, as well as international favorites like pizzas and pastas. The relaxed atmosphere, combined with live music on select evenings, makes it a must-visit spot for both lunch and dinner. The seafood pasta is a must, and their grilled lobster? Absolute perfection.
20 Knots – Shoal Bay East
A 3-minute drive or a leisurely 10-minute walk away from The Fountain is 20 Knots, the chic-yet-relaxed beachfront restaurant at Zemi Beach House on Shoal Bay East. 20 Knots is the kind of place where time slows down, and every bite feels like a mini vacation. 20 Knots takes the bright, sun-drenched flavors of the Caribbean and weaves them seamlessly with Mediterranean influences, creating a menu that’s both comforting and exciting.
If you love light, zesty, and ultra-fresh seafood, this dish is a must. Imagine tender chunks of just-caught fish, marinated in citrus juices, kissed with a hint of heat from local peppers, and topped with fresh herbs. Every forkful is a burst of tropical sunshine.
As a seafood lover, the Lobster & Mango Salad is everything! Nothing says Anguilla indulgence like sweet, buttery lobster tossed with ripe, juicy mango, fresh greens, and a delicate citrus dressing. This salad is equal parts refreshing and luxurious.
For the foodies who prefer meat or veggies, 20 Knots has something for you too. And of course, you can’t forget dessert. The coconut panna cotta is light, creamy, and delicately sweet, while their chocolate lava cake is pure decadence—think warm, gooey chocolate oozing onto your plate, just waiting to be devoured.
Tropical Sunset – Shoal Bay
Tropical Sunset is a favorite for those who want simple, delicious food without the fuss. It’s the kind of place where you can linger over a cocktail and let the ocean waves set the rhythm of your evening.
We would recommend this spot for lunch! Their grilled snapper, conch fritters, and a killer rum punch are what you should order when you get here. This spot is the definition of no-frills, all-flavor island dining. The vibe is relaxed, the drinks are cold, and the view? Straight-up mesmerizing.
Just a few more minutes away are some noteworthy foodie spots.
The Pit Stop by Ben – Island Harbour, Anguilla
This roadside restaurant is approximately a 10-minute drive away from The Fountain. For those seeking an authentic local experience, The Pit Stop by Ben offers traditional Anguillian dishes in a cozy setting. Known for its hearty portions and friendly service, the menu features items like grilled crayfish, stewed goat, and a variety of seafood options. It’s an excellent spot to immerse oneself in the island’s culinary traditions.
Artisan – Island Harbour, Anguilla
Artisan is not just a restaurant, it’s an experience, a love letter to authentic Italian flavors and a haven for pizza lovers. But we’re not talking about just any pizza; we’re talking about wood-fired, Neapolitan-style masterpieces, the kind that have crispy, charred edges, a pillowy-soft center, and ingredients so fresh you’d swear they were flown in straight from Italy.
With its cozy, open-air setting, the ambiance here is effortlessly romantic and rustic, making it perfect for a relaxed dinner under the stars. Whether you’re a self-proclaimed pizza connoisseur, a lover of fine wines, or someone who simply appreciates the magic of good food made with heart, Artisan Anguilla is a must-visit. And with it being just a 10-minute drive from The Fountain Anguilla, there’s really no excuse not to indulge in a night of wood-fired bliss.
Hibernia Restaurant & Art Gallery – Island Harbour, Anguilla
Hibernia offers a unique dining experience by combining exquisite cuisine with an art gallery showcasing pieces from around the world. The menu is an eclectic mix of Asian and European influences, featuring dishes like Thai-style fish and duck breast with tamarind sauce. The serene garden setting and curated art collection enhance the overall dining experience.
Be sure to visit here and ask for Mary Pat, one of the owners, she is the sweetest! And because it’s only approximately a 10-minute drive away from The Fountain, you should definitely schedule this in your itinerary.
Scilly Cay
Just off the coast of Island Harbour, on Anguilla’s northeastern side. Hop on a free boat ride from Island Harbour only takes 2 minutes. Getting to Scilly Cay is half the fun. Simply head to Island Harbour, wave to the boat operator (Yes, literally just wave your arms!), and they’ll whisk you across the shimmering blue waters. No reservations, no schedule just classic, carefree island style.
Scilly Cay is famous for its mouthwatering seafood, grilled fresh to order over an open flame. The lobster, crayfish, and snapper are cooked to perfection, seasoned with Caribbean spices, and served alongside hearty rice and salad. The portions are huge; you’ll want to bring a big appetite!
A trip to Scilly Cay isn’t complete without their world-famous rum punch. Made with at least three types of rum, a splash of tropical fruit juices, and an extra kick of island magic, this drink is not for the faint of heart. Locals say one punch will relax you, two will make you dance, and three…well, good luck getting off the island! Sip slowly; this punch is dangerously strong!
Let’s go over to Sandy Ground, which is about 15 minutes’ drive away from The Fountain.
Dolce Vita – Sandy Ground
Sometimes, you just need Italian comfort food. Yes, even in the Caribbean. Dolce Vita delivers homemade pasta, dreamy seafood dishes, and a romantic waterfront setting that will make you want to stay forever.
Dolce Vita is a place where flavor, passion, and hospitality come together in the most delicious way possible. Whether you’re a pasta connoisseur, a wine lover, or simply someone who appreciates a truly outstanding meal, this is a must-visit spot during your time in Anguilla.
With an extensive wine list and dishes bursting with authentic Italian flavors, Dolce Vita brings a little slice of Italy to the Caribbean. Whether it’s a romantic date night or a family gathering, this spot never disappoints. The Cioppino and Nutella cheesecake will change your life, guaranteed.
And with just a 15-minute drive from The Fountain Anguilla, getting there is as easy as twirling a forkful of homemade fettuccine.
Roy’s Bayside Grill – Sandy Ground, Anguilla
This is a favorite spot for a hearty breakfast! Roy’s Bayside Grill is a beloved establishment known for its British-inspired menu and beachfront location. Guests can indulge in dishes like fish and chips, shepherd’s pie, and fresh seafood platters. The relaxed atmosphere and regular live music events make it a popular spot for both locals and tourists.
Straw Hat Restaurant – Meads Bay
About a 20-minute drive from The Fountain imagine sitting seaside, toes buried in the warm sand, while a salty ocean breeze flirts with your senses. Now add a plate of fresh, buttery snapper, a piña colada that tastes like pure sunshine, and the smooth sound of waves kissing the shore. That’s what you get at Straw Hat. The coconut cake alone is worth the trip.
The restaurant’s atmosphere balances refined dining with a relaxed, island-chic aesthetic. Locals and visitors alike rave about the service; warm, welcoming, and always ready with an excellent wine pairing recommendations. Whether you come for lunch or a candlelit dinner, every moment at Straw Hat is a sensory delight. The jerk-spiced mahi-mahi is a knockout, and their famous coconut cake is nothing short of legendary.
Blanchard’s Restaurant– Meads Bay
Like Straw Hat, Blanchard’s is about 20 minutes away from The Fountain. Blanchard’s is the kind of place you walk into and instantly feel at home, except this “home” happens to serve some of the most delicious Caribbean-inspired dishes you’ll ever taste. The outdoor patio is draped in twinkling lights, and there’s a laid-back yet elegant vibe that makes everything taste even better.
Blanchard’s menu is a love letter to the island’s vibrant flavors, crafted with a touch of sophistication. Their commitment to fresh ingredients and bold flavors makes every dish sing. Their coconut-crusted grouper is practically a work of art, and the lobster risotto? Heavenly. Whether you’re in the mood for seafood, steak, or a tropical-inspired vegetarian dish, they’ve got you covered.
Jacala – Meads Bay
An elegant yet effortless beachfront French-Caribbean bistro where the chefs greet you like an old friend and every dish feels like a love letter to flavor—that’s Jacala. It’s intimate, refined, and the kind of place you’ll dream about long after you leave.
Here, dining is an experience, with dishes plated so beautifully you almost hesitate to take the first bite. But once you do? Pure bliss. The menu is carefully curated, with French-inspired techniques complementing the fresh, locally sourced seafood. Their grilled crayfish is melt-in-your-mouth perfection, and the foie gras? Pure indulgence.
Sharky’s Restaurant – West End, Anguilla
Approximately 25 minute drive away from The Fountain, Sharky’s is a gem known for its warm hospitality and flavorful Caribbean dishes. The menu includes favorites like jerk chicken, coconut crusted fish, and a variety of vegetarian options. The intimate setting and personalized service make it a standout choice for those seeking an authentic dining experience.
Sunshine Shack – Rendezvous Bay
The distance from The Fountain Anguilla to Sunshine Shack is a 25-minute drive. If you want the true, toes-in-the-sand, sun-on-your-face beach shack experience, Sunshine Shack is your place. Owned and run by the ever-welcoming Garvey Lake, this iconic beach bar and grill is a slice of pure Caribbean joy. Expect reggae beats, friendly faces, and a barbecue that sends mouthwatering smoke signals across Rendezvous Bay.
The name of the game here is grilled perfection. Whether you go for the grilled ribs, jerk chicken, or fresh-caught fish, every bite is kissed by the smoky flavors of an open-flame barbecue. Their shrimp skewers are another knockout—plump, juicy, and lightly charred, served with Garvey’s signature hot sauce for that extra kick.
And let’s not forget the sides—fluffy coconut rice, sweet plantains, and crisp coleslaw round out the plates perfectly. Pair it all with an ice-cold Carib beer or a rum cocktail, and you’ve got the recipe for an afternoon you won’t want to end.
If you’re lucky, Garvey might even hand you a permanent marker and invite you to sign your name on the walls or furniture—because at the Sunshine Shack, everyone is family.
D’ Richard’s – Aurora
About 25 to 30 minute drive away from The Fountain, if you’re craving a refined yet unpretentious dining experience, D’ Richard’s is where you want to be. This hidden gem manages to blend casual comfort with gourmet finesse, making every meal feel like a special occasion even if you just wandered in straight from the beach.
The seafood pasta is legendary, generously loaded with succulent shrimp, scallops, and local lobster, all drenched in a rich, creamy sauce with a whisper of island spice. If you’re in the mood for something heartier, the slow-braised short ribs practically melt off the bone, served alongside buttery mashed potatoes and seasonal veggies.
And let’s talk drinks, because what’s a Caribbean evening without one? Their selection of wines and craft cocktails make it easy to linger a little longer under the warm, twinkling lights.
Final Thoughts: Your Anguilla Food Bucket List Awaits
If you’re a foodie, Anguilla is your dream destination and should be on your must-go list! Whether you’re indulging in fine dining or digging into fresh seafood at a beachside shack, every meal here feels like a special occasion. From Meads Bay’s oceanfront elegance to Shoal Bay’s laid-back charm and Sandy Ground’s lively nightlife scene, there’s a culinary adventure waiting at every turn.
And for the perfect home base to experience it all, Fountain Anguilla offers a luxurious yet comfortable stay in our Fountain Anguilla villa rentals just minutes away from these incredible dining spots. Book your stay today in one of our studio penthouses and turn your food-filled getaway into an unforgettable island escape in our rentals!
So, grab your fork, pack your appetite, and get ready to eat your way through paradise. Bon appétit, and happy feasting!
At The Fountain Anguilla, we believe your journey to paradise should start from the moment you book your stay. This February 5th, we’re celebrating Book Direct Day 2025, and we’re here to share why booking directly with us is the smartest, most rewarding choice you can make.
Unlock Exclusive Savings
Why pay extra when you can enjoy unbeatable savings? Booking directly with The Fountain means skipping third-party fees and hidden costs. We guarantee the best rates when you book with us, and you’ll often find exclusive offers and special promotions that only direct bookers can access. Think discounted room rates, complimentary perks, and fabulous package deals—all designed to make your dream getaway even more affordable. Plus, by booking directly, you’ll avoid the mystery fees that often appear on third-party platforms, leaving you more to spend on enjoying your trip.
Flexibility to Keep You Stress-Free
Life is full of surprises, and travel plans can change. Booking directly with us gives you the peace of mind that comes with flexible policies. Whether you need to adjust your dates or upgrade your room, we’re here to help without the rigid restrictions or fees you’ll often encounter on third-party platforms. We’re all about making things easy and stress-free for you. Need to move your stay to another week or make adjustments to your itinerary? We’ll work with you to ensure your plans align perfectly with your needs.
Personalized Experiences Just for You
When you book directly, you’re not just a guest; you’re part of The Fountain family. Our dedicated team is here to ensure every detail of your stay is perfect. Want a room with a view of the sparkling ocean? Need help planning a romantic surprise? Looking for early check-in after a long journey? We’re here to make it happen. With direct booking, you’ll enjoy personalized service that turns a great vacation into an unforgettable one. Your preferences matter, and by working directly with us, we’re able to craft an experience that feels uniquely yours.
Special Extras to Enhance Your Stay
Let’s talk about the extras because who doesn’t love a little something special? Booking direct comes with exclusive perks like room upgrades, early check-in, and late check-out. Imagine being greeted with a chilled bottle of wine or waking up to the sound of waves in an upgraded suite. These thoughtful touches are our way of saying thank you for choosing The Fountain. Direct booking often opens the door to surprises that elevate your experience and make your time with us even more memorable.
Support Local and Feel Good About It
When you book directly, you’re supporting a locally owned business that’s deeply rooted in Anguilla’s vibrant community. Unlike third-party platforms that take hefty commissions, your booking dollars stay right here, helping us create jobs, support local businesses, and enhance our beloved island. It’s a win-win for everyone. You get an amazing vacation, and we get to keep the spirit of Anguilla alive and thriving. Knowing your choice positively impacts our community makes your stay even more meaningful.
Privacy and Security You Can Count On
Your peace of mind matters to us. When you book directly through our official website or contact us, your personal information stays safe and secure. Unlike third-party platforms that might share your details, we handle everything with care, ensuring your data is used solely to enhance your stay. Booking direct means you can relax knowing your details are in trusted hands.
Insider Tips from the Pros
Our team doesn’t just work here; we live and breathe Anguilla. Booking directly means you’ll have access to our insider knowledge, from hidden beach spots to must-try restaurants and unforgettable experiences you won’t find in a guidebook. Let us help you uncover the magic of Anguilla, one personalized recommendation at a time. Whether it’s a secluded cove perfect for a sunset swim or the best spot for fresh seafood, we’ll make sure your stay is filled with unforgettable moments.
Exclusive Rewards
This February 5th, we’re rolling out the red carpet for our direct bookers with exclusive offers and surprises. Keep an eye out for limited-time promotions and perks that will make your stay even more delightful. By booking directly, you’re not just reserving a room, you’re choosing a more personalized, flexible, and rewarding travel experience. Whether it’s complimentary amenities or added discounts, Book Direct Day is your chance to indulge in extra luxury.
Seamless Booking Made Simple
Gone are the days of complex, time-consuming bookings. Our website is designed with you in mind, offering a smooth, hassle-free process from start to finish. Prefer a more personal touch? Our friendly team is just a call or email away, ready to assist with your reservation and answer any questions. We’re here to make sure your booking experience is as enjoyable as your stay.
Simplifying your Book Direct Day 2025
Ready to start your journey to paradise? Booking directly with The Fountain is quick, easy, and secure. Visit our official website, call us, or drop us an email, and our friendly team will guide you through every step. We’re here to help you craft the perfect Caribbean getaway.
Celebrate Book Direct Day on February 5th by making The Fountain Anguilla your home away from home. We can’t wait to welcome you with open arms and island charm. From exclusive perks to personalized service, booking directly is your passport to the ultimate vacation experience. Don’t just visit Anguilla, immerse yourself in its beauty, warmth, and hospitality with The Fountain as your guide!
Let us start by saying that Anguilla is NOT the cheapest island in the Caribbean. After all, it is a luxury island where the rich and famous come to escape the tourist-heavy scene and the bothersome fans. The exclusive and high-standard reputation that precedes Anguilla can deter some other potential travelers who are not as wealthy as Madonna and LeBron (who have both made recent vacations here). With the global gaze on our island increasing, of course more people want to come here! But because they think they can’t afford that trip to the famous Anguilla, they hesitate to book their flight. Here’s our Insider’s Guide and Cheat Code for Vacationing in Anguilla.
We’re sure that guests who have visited and stayed on the island before, though they absolutely loved it, wished they had a friend on the island to show them around so they could experience the island from a local perspective. Well, we have some great news for them (if any of those beautiful people are reading this) and for anyone who wants to visit for the first time: You have just come across your new island bestie! We will be handing you your exclusive behind-the-scenes “local Anguilla” access. We’ll let you in on how you can vacation in Anguilla for best rates and experience and tell you about some places where you can get the most out of your money.
Below, we will take you to some of the freshest food and drink spots that won’t wreck your budget and also give you a few essential tips about the island and moving around while here to help you have a seamless travel experience and stay on the island. By the time we are halfway through, you’ll be packing your suitcases at lightning speed to get here—so, let’s go!
TIP #1: The Best Time to Travel on a Budget to Anguilla Is During August
One of the first and most important things you need to consider when planning a trip to any vacation destination is finding out the best time to go there. Most islands and the properties on them would NOT share this information with the public, and especially incoming guests.
Hence, our first tip is top-secret, backstage pass information, that almost feels illegal to share (but it’s not).
August is the time when costs for rental properties decrease, as it is the ending of the tourism season and the beginning of the hurricane season in the islands.
Because most places that close during the off-season are not closed yet, and the island’s tourist population decreases significantly, it is less hassle to secure reservations such as dinner and excursions. This is also the time that we have our carnival season, when we celebrate our love for the island with lots of real Anguillan food, drinks, music, events and colorful costume parades. The month of August is recommended for visitors who desire to save some money on bookings and enjoy the local culture.
TIP #2: Book Your Stay at CéBlue Luxury Villas, The Fountain, or La Vue Boutique Inn.
Any of these properties are highly recommended for guests who seek quality lodging and exceptional service at an affordable rate.
- CéBlue Luxury Villas is well known for its exceptional service and its amazing views overlooking the ocean, where you can enjoy the most breathtaking sunsets. This luxury villa is fully stocked with opulent amenities and superior services, including private chef and personal concierge.
- La Vue Boutique Inn is affordable, yet tastefully designed with modern rooms that overflow with personality, making you feel right at home. La Vue is also ideal for business meetings and working remotely, as it has a super spacious, comfortable and well-equipped Conference Room! You can experience the classic island setting and indulge in hospitality without compromise at La Vue Boutique Inn.
- The Fountain feels like an oasis. It almost doesn’t match its surroundings, in the most delightful way. The Fountain is located on one of the most spectacular beaches of the island, Shoal Bay, but is nestled away behind gorgeous greenery in a cool and tranquil escape. Your stay here will be without a doubt a delightful one.
When you’ve selected one of the above, you’ve already saved at least $1000 in comparison to the other pricey locations. You’re welcome in advance!
TIP #3: Book with Our Vacation Experts to Save Money
Many people think they get the best deals if they book everything on their own, but the lie detector determines “That is a lie!” Before you even get to the island, our third tip is to let our team assist you with booking everything from accommodation to tours and activities. Please, please, please, if you have not visited the island before, this will help tremendously for three reasons: We have direct contact with the local companies, can provide you with the most cost-effective options for transportation, and our service and assistance is FREE!
TIP #4: Travel with Some Cash
If you land in St. Maarten when coming into Anguilla, you will be required to pay immigration taxes in person at the ports, not included in the cost of the trip. If coming by boat, the porter works for tips, so some cash would be wise and convenient.
TIP #5: Book a Rental vs. Taxi Service
Simply put, it is more economical to rent a vehicle for your stay here. Though we drive on the left side of the road, it is quite easy to get around the island. The roads are wide and are all connected to one main road. Anguillans are super friendly too, so in the highly unlikely event that you “get lost,” you can literally ask any local and they would gladly point you in your desired direction.
Once you have arrived and had a seamless travel experience to our island and to your location, for the cheapest option possible, you are off to an excellent start to an unforgettable vacation!
TIP #5: Eat Where Locals Eat!
Now, if you don’t like to eat local, and you don’t like epic food joints, this section is not for you! We’re about to let you in on some of the underrated restaurants, hot spots where locals hang, and activities you can indulge in that we enjoy doing as residents of this gem island. We’re not saying that the locals don’t dine at our fine restaurants, because they are exquisite, and the meals are immaculate! However, that is not the norm for majority of the local population. Below, we’ve created a list for you of some places that would give you an exclusively Anguillan type of experience.
The Strip
The Strip is located smack in the center of the island, in the capital, The Valley.
This is a short stretch of “hole in the wall” kind of bars and restaurants on both sides of the road. They have a melting pot of culture here. Along with the vibrant music played on speakers, you will find, barbeque on the grill, food from different islands, pizza, authentic Anguilla meals and even Indian food!
Sharpys and Good Korma are two hidden gems amongst the pool of restaurants here.
Sharpy’s has the authentic Anguillan meals daily! Serving the national dish of rice and peas and fried fish almost always. Almost all their delicious meals; Grilled Mahi Mahi, Fried Jacks, Sauteed Shrimp, Stewed Chicken and so much more are under $20.00.
Now, Good Korma is one of the very few Indian restaurants on the island. This is one of our favorites because of their drinks, though. They have the best bartender on the island! When you go here, you must ask for Joash to make you your favorite drink. We guarantee it will be the best you’ve had. And because this place is not very often visited by tourists, it is ideal if you want to escape the usual tourist-heavy scene. You will feel right at home and have fun here for sure!
BBQ
Jelly BBQ, Ken BBQ, B&D’s, and DBBQ Hut are all excellent options for some savory grilled meats and veggies served with any side of your choice that’s available done the island way, on the outside cast iron grills. These spots are ideal for an on-the-go quick stop to fill up when you’re exploring the island.
Coffee
Calling all the coffee lovers! Coffee O’Clock has an array of barista quality coffees, hot beverages, and yummy breakfast items for under $10 for every item. Though there are bakeries that are cheaper, where you grab and go, and breakfast places that are more expensive, where you can sit and dine, Coffee O’Clock offers the best of both worlds. It’s a cozy café where you can sit, relax, enjoy a good book and some great coffee.
Pizza
Both Corner Bar and J&J’s pizza places are owned and operated by local families. They are the locals’ favorite pizza spots and have the islanders divided because of their distinctive tastes. Corner Bar serves the savory for those who prefer the more Americanized pizza, and J&J’s serve the to the other half, a flat pizza with a sweeter dough, unique to this island. Try them both!
Fruity Web
In contrast to the BBQ meals and pizzas, Fruity Web is a healthy alternative on the island. This little shack off the beaten path is easy to miss as you drive past it tucked away on the side of a main road. Fruity web is ideal for the health conscious who want to enjoy our culture while eating clean! They serve vegan or “ital” meals, refreshing fruit and vegetable smoothies and a wide array of tropical fresh produce. Be sure to sit under one of their little umbrellas in the shade as you take a respite from the sun.
Mirabelle’s Rooftop
If you want a little excitement and want to experience night life, this indoor/outdoor rooftop bar, night club & restaurant in the heart of Anguilla is the place to go! With an extensive sushi offering, international tapas & fun cocktail options, Mirabelle’s is a must visit. Mirabelle’s is owned and named after a very proud Anguillan and is a spot popular with locals for ‘fast casual’ dining, drinking, and partying.
Beach Restaurants
Tropical Sunset & Chriss Conch Shack are both perfect for that toes-in-the-sand experience the rich, famous, budget watchers and locals all anticipate! At Tropical Sunset, you’ll find fresh fabulous fried fish! That is all we have to say, because it’s a tongue twister if you say it too fast!
Conch Shack is actually one of our favorite spots to go on off days for some juicy conch patties that are only sold here! We get more than one every time because we love them so much. Sitting on two stunning beaches, Shoal Bay and Sandy Ground, respectively, the views, the service, the prices, and the experience are outstanding.
Zack Shwarma
Zack Shwarma serves all Lebanese cuisine at reasonable prices. It is a dine-in and take-out spot that is open past 12am. They serve large portions for lower prices, about 50 – 70% cheaper than restaurant meals. We would suggest ordering ahead of time, as they get very busy, especially being one of the very few places that are open after hours on the island.
South Valley Community Street Festival
If you took our first tip and booked to travel here during carnival time, you will be privileged to enjoy this fully immersive experience. The plethora of booths with unlimited types of food and cultural items on display and for sale will have you giddy with excitement, because there’s so many things to see! Some of the food booths even offer you free samples. So, you may most likely end up leaving there having spent way less and eaten way more than you could in a week (Ok, we’re, exaggerating, maybe enough for two days) on the island. It’s a wonderful time to experience the local food, culture, and mingle with the people of the island.
TIP #6: Make Use of the Local Food Delivery Services
If you are not a driver and are too far away from food to walk, instead of calling a taxi, you can call or WhatsApp to order at Changes Bar and Restaurant and a few other restaurants.
TIP #7: Do What the Locals Do!
Beach, beach and more beach! When it comes to the beaches of Anguilla, there’s no denying the allure. The stunning white sand between your toes, the gentle crash of sapphire waves, and the warmth of the sun. It’s a sensory experience like no other and one you should not skip. If you don’t do anything else during your stay here, let visiting the beaches be one thing you do! It’s free, free, free, and you will create remarkable memories that you can and will cherish for a lifetime.
TIP #8: Avoid the Crowds by Heading to Scenic Spots Early in the Day
Those who do will be rewarded with the sight of the clear skies and blue-green waters of the island. This is the optimum time to bask in the warm rays of the sun and savour the views undisturbed. Perfect for capturing photos too, as the lighting is not too harsh.
TIP #9: Shop Local for Souvenirs and Keepsakes
Sea Spray Tropical Gift Shop, Sand & Salts, and Glo Rum all provide more than products. They each offer unforgettable experiences that you will enjoy, such as local rum sampling (Glo Rum), margarita and tequila sampling (Sand & Salts), and even smoothies and rum punches (Sea Spray). Be sure to visit these spots before you leave!
TIP #10: Make Friends with the Locals!
And now, our final, most simple, and maybe most important tip during your stay in Anguilla is to make friends with the locals! This is actually something that won’t be very hard to do, because we are some of the friendliest people you will ever come across—no exaggeration this time. We challenge you to strike up a conversation and mingle with the people of the island; this will amplify the impact of your experience. After all, we live here, we know the place and enjoy living here and will share that with you.
We hope you enjoyed our vacationing in Anguilla guide. With that being said, we hope to see you soon. All of us at Fountain Anguilla, and the entire population of Anguilla, are eager to welcome you to our shores!
If you’re talking about picturesque beaches and stunning clear waters, you can’t have the conversation without mentioning Anguilla. With sand so brilliantly white, your favorite pair of shades are a must have when travelling here! Anguilla is a top-tier destination for travellers seeking a vacation that’s relaxing and equally luxurious. This jewel of the Caribbean offers a peaceful atmosphere that contrasts with more tourist-heavy Caribbean Islands. Whether you’re looking to relax by the beach, indulge in gourmet dining, explore the island’s cultural heritage, or engage in water sports, Anguilla offers the perfect summer getaway. Below, we’ll tell you how you can make the most of your summer vacation in Anguilla in our Ultimate Summer Vacation in Anguilla guide. Including a detailed 7-day itinerary that will leave you revitalized, enriched, and longing for more.
Why Choose Anguilla?
Before we jump into creating the ideal itinerary, let’s see some of the reasons why you’d want to make Anguilla your destination of choice in the first place:
- The Beaches Are Stunning – Some of Anguilla’s beaches have been named amongst the top 10 in the world (Shoal Bay). And that is no surprise, because Anguilla is home to some of the most breath-taking beaches you will ever lay your eyes on.
- The Accommodations Are the Finest – When considering where to stay on island, there are so many options, such as luxury resorts where you can indulge in exotic and fine dining experiences, luxury villas such as CèBlue Luxury Villas with unparalleled service and gorgeous sunset views, and cozy hideaways like The Fountain, where you can relax in an oasis accentuated by lush gardens are all ideal places to stay in Anguilla.
- The Culinary Scene Is Superior – This small island packs a big punch in the dining scene. Boasting over 70 restaurants, this beautiful island is famous for its fresh seafood and fine dining. From beachside seafood shacks such as DaVidas Bayside to world-class restaurants like D’ Richard’s at Aurora Resort, Anguilla is definitely the “cream of the crop” when it comes to your tastebuds being satisfied.
- Water Activities Are Ever-Present – After all, water IS life, and even before landing in Anguilla, you will notice when you look out your plane window the several shades of blue, alluding that water is an inescapable part of your experience during your stay here. Snorkelling, diving, kite surfing and sailing are just a few of the activities that allow you to explore the vibrant water world of Anguilla.
If that preview hasn’t tantalized you and made you eager to start packing for the trip of your lifetime, then allow us to entice you further with an itinerary that will have you craving this extraordinary island. Let’s finally dive into the ultimate 7-day itinerary for your Anguillan summer vacation!
Day 1: Arrival and Settling In
Morning: Arrive in Anguilla
Many visitors, fly directly into Anguilla through Clayton J. Lloyd International Airport or arrive by boat from St. Maarten. Most visitors choose to fly into Princess Juliana International Airport in St. Maarten and then take a 25-minute ferry ride to Anguilla. We recommend these arrangements be pre-booked with your hotel or resort’s concierge if possible. Upon arrival, you’ll be welcomed by Anguilla’s warm breeze, sapphire waters and pleasant smiling faces of the locals.
Afternoon: Check-In at Your Resort or Villa
For a luxury experience, consider staying at CèBlue Luxury Villas or The Fountain. Each destination offers a unique experience. However, they both offer outstanding service and world-class amenities with striking ocean views.
Evening: Welcome Dinner
If you’ve decided on staying at CèBlue Luxury Villas, for the night of your arrival, they welcome you to a local dining experience in the comfort of your villa. Their inhouse chef delivers the most succulent and savory barbeque meal for you and your family. So, if you are interested in tasting authentic Anguilla while sunset gazing on our isle of paradise, this will be perfect. But, if you have decided to stay elsewhere, Ocean Echo, located on Meads Bay Beach, is the perfect introduction to Anguilla’s culinary scene. Enjoy international & Caribbean cuisine and sip on a refreshing spritzer as the salty ocean breeze blows through your hair.
Day 2: Exploring the Best Beaches of Anguilla
Morning: Shoal Bay Beach Visit
Start your first full day in paradise by visiting Shoal Bay East, one of the most beautiful beaches in the world! The expansive shoreline of powder-soft sand and clear turquoise waters provide the ideal setting for swimming, sunbathing, and snorkelling. Get out your sunscreen, grab a cold refreshing drink from one of the bars, and soak up some Caribbean rays on this world-renowned beach.
Afternoon: Lunch at Madeariman
While on Shoal Bay Beach, enjoy a delicious beachside lunch at Madeariman Restaurant. Order the Mahi Mahi kebab with Creole sauce or a lobster pizza and pair it with a refreshing tropical drink. We guarantee you will enjoy the phenomenal setting, tasty meals, and friendly atmosphere.
Stop at Sunshine Shack
Spend the rest of the afternoon at Rendezvous Bay, another one of Anguilla’s finest beaches. Head to Sunshine Shack, where you will experience true island vibes! The bright coloured umbrellas, aroma of BBQ and sounds of reggae with a view of St. Martin in the distance immediately puts you in a mellow state of mind. Be sure to ask about Garvey’s famous BBC (Banana Baileys Coconut) smoothie, and don’t forget to take some pictures while you are there!
Evening: Fine Dining
Before you head back to your accommodation, it’s time to get ready for a fine dining experience at Pimms, located at Cap Juluca/Belmond Property. Sitting right on the ocean’s edge, this restaurant oozes an ambience of romance and elegance. Get a seat facing the water and sit pretty while you enjoy the gourmet dishes and dreamy atmosphere.
Day 3: Lavish Island Life
Morning: Sandy Island & Prickly Pear
Now that you got your feet wet on Anguilla’s shores and washed the salt off your face from the day before, it’s time to splash through our waters again on an unforgettable boat excursion to our offshore cays! Visiting Sandy Island is a must-do! Many describe Sandy Island as a “tiny spit of sand,” but after visiting, you will agree that it is in fact a slice of bliss. When approaching Sandy Island, be prepared to jump in the glassy water to get to shore, as it’s the only way. So much fun! Head straight to the bar and order a frosty cold drink as you lounge and bask in the dream-like beauty of the island. Peace is an understatement.
Afternoon: Lunch at Prickly Pear
After you’ve settled into your Zen mode, your boat crew will escort and assist you back on to the boat in true celebrity fashion and continue your journey over to Prickly Pear. This island is home to unspoiled white sand beaches and inhabited by iguanas, crabs, and bananaquit birds. When approaching the sparkling shores, as you guessed, time to jump in again! The Prickly Pear Team will greet you as the royalty you are and guide you to the restaurant, where you will enjoy a succulent lobster meal and refreshing drinks with your toes in the sand. If you can muster up the energy to move after being stuffed with the large serving of food, you can spend some time swimming in the warm waters or simply relaxing on the soft sands before heading back to mainland Anguilla.
Evening: Dinner at SAVI Beach Restaurant
Keeping with the theme of superstar experience on this luxury island, it’s time to get dolled up and get dressed up to head to a larger-than-life restaurant for dinner. You will want to charge your phone or camera fully before leaving your resort for this one, because you will want to capture and have memoirs of this unique experience. SAVI Beach Restaurant is a whole mood! The aesthetics of the architecture and design are striking with unique features throughout the property. This chic spot is super modern and hip. And with meticulously plated delectable meals you will be left impressed and have an increased appetite for authentic Japanese and Italian cuisine. During your stay in Anguilla, be sure to dine at this showstopper.
Day 4: History & Culture
Morning: Breakfast at Village Bake House
Because you’ve been spending lots of time on the water since you got here, it’s time to explore the land of Anguilla. We recommend you start your day with breakfast at Village Bake House. This is a quaint and cozy French bakery with a wide variety of crispy pastries, freshly baked breads, and piping hot beverages that are sure to wake up all your senses in the morning. You will enjoy the scrumptious assortment of breakfast items and desserts on a charming patio somewhat hidden behind a wall of hanging plants with sunlight peeking through. Almost magical!
Art Galleries Tour
Anguilla may be small, but it is rich in history and culture. So, after filling up your tanks (your tummy and the car), drive out to discover the island’s art scene. For the independent travellers, you can explore on your own, if not, there is also the option to hire a tour-guide to visit these places. Anguilla has a thriving art community. Spend your day visiting local art galleries, such as Devonish Art Gallery, which features unique sculptures, pottery, and paintings by local artists. You can also explore Lynne Bernbaum’s Art Gallery for vibrant, Caribbean-inspired artwork.
Afternoon: Lunch at Jacala
After your cultural excursion, stop for lunch at Jacala. If you’ve ever heard of Anguilla’s dining, you must’ve heard about Jacala. It is almost impossible to get into this restaurant for dinner OR lunch without making reservations way in advance. Simply put, their food is outstanding. Their notorious dish is their Steak Tartare, and Lobster Soup is a top choice for any palette. As you wait for your lunch to be served, sink into your seat, sip on some Pinot Noir and appreciate the restaurant’s open-air designed terrace and uninterrupted panoramic views of the Caribbean Sea.
Evening: 4Shore Fishing
How can you truly say you’ve experienced the island without actually doing what the locals did and do? You can’t. Fishing is a major part of Anguilla’s history that has helped built its present economy. That is why we suggest that you book with 4Shore Fishing to experience a memorable and remarkable fishing excursion. These two skilled and professional brothers are the only ones qualified to take you on this onshore fishing adventure. The thrill of successfully catching all those huge fish will have you “hooked” on the adrenaline rush during this memorable experience.
Dinner at Tasty’s
Now that you may have an appetite for some freshly caught fish, Tasty’s Restaurant is the place to go. Tasty’s Restaurant is a local favourite for traditional Anguillan cuisine and is known for having the freshest, most extensive selection of seafood! If you are sea-sick and want a brief break from the seafood, you can try the johnny cakes or goat curry for an authentic taste of the island. Locally owned, locally sourced ingredients, with local cuisine prepared by a local chef—you can’t go wrong ending your cultural day with a meal here.
Day 5: Free-style Leisure
Morning: The Arch & Meads Bay Beach
It’s day five, and there’s still so many things left to do. Surprised? You shouldn’t be! Anguilla is small, but not short of activities and sights to see. For this day, you can visit Anguilla’s landmark, The Arch. This natural land and sea formation is something you should definitely put on your to-do list of things to see while in Anguilla. The beaten shoreline, the jagged sea cliffs perfectly carved out, the several shades of blue and green of the water slamming the base of the arch—it all comes together majestically, making this a very scenic photo stop.
The photo stop at The Arch won’t take too long, so you will be able to take a peep at another breathtaking beach before you head to another must-do on this itinerary. The midday sun brings out the vibrancy of this particular beach. With waves dancing playfully and the breeze warm and cheerful. Once you get there, you will see that Meads Bay Beach is very lively on its own.
Afternoon: Lunch at Cap Shack
Off to lunch at Cap Shack on powdery shores. The view is breath taking and the atmosphere is more of an elevated casual scene. Cap Shack’s stylish cream and pastel blue vintage food truck is where the most unique flavoured, mouth-watering tacos are made! With seats and tables set in the sand, facing the glistening ocean, the only way to properly experience this lounge and lunch is bare feet with a colourful cocktail or mocktail in your hand, leaving you feeling and looking cool.
Evening: Night Kayak with Liquid Glow
This next adventure is a MUST DO for anyone looking for a unique and thrilling experience!
Night kayaking is a rare and exhilarating opportunity that allows you to explore the waters in a different way. Anguilla boasts some of the most pristine waters in the Caribbean, which makes for perfect kayaking conditions, and when it comes to kayaking in Anguilla, the experience is even more special. Paddling through the amazing crystal-clear waters in your 100% transparent and luminescent kayaks allows you a spectacular underwater view at night, attracting fish to your kayak while you follow the tour guide to many underwater attractions. You’ll have the opportunity to see marine life in a different way. It’s an experience you won’t want to miss.
Dinner at DaVida’s Restaurant
Located on idyllic Crocus Bay is DaVida’s Restaurant. This is perfect location to unwind and enjoy delightful tapas, fresh seafood dishes like their snapper and signature grouper. After a long day, sip on an island inspired cocktail as you witness the most beautiful array of yellow, orange and pink hues as the sun sets in the horizon.
Day 6: Road & Water Adventures
Morning: Rent a MOKE
For this segment, we highly recommend you and your family or friends rent a MOKE for the day. There is no cooler way to travel around on your island getaway than in one of these classic vehicles. These cute cars have waterproof seats, sunroof tops, and come in different fun colours that you can sometimes choose from to match the vibe of your vacation. Having a MOKE for the day is ideal for road and water adventures!
Snorkelling & Water Sports
Travel on your trendy ride down a bit of a rugged slope to Crocus Bay for a fun day of water activities, including kayaking, stand-up paddleboarding, and pedal boating. When you get to Crocus Bay, you will realize that it is quite unique, as it is the only beach in Anguilla that boasts a golden shoreline! The calm bay here is perfect for exploring the coastline. Surrounded by clear, shallow waters, the bay is perfect for snorkelling. You’ll have the chance to swim with sea turtles and a variety of tropical fish along the coastline from Crocus Bay into a small cove called Little Bay. Whether you are exploring the reef by either snorkelling or scuba diving, or you are pedalling your way to Little Bay, this is the ultimate spot to make memories with friends and family.
Afternoon: Lunch at DaVidas Bayside
While on Crocus Bay, make sure to order and indulge in a tasty meal, because inevitably you will be hungry after hours of splashing in the water and soaking up the sun rays.
Then chill out under the leafy palm trees as a cool respite from the sun and take pleasure in the simple things, like being blessed to be on an island as enchanting as Anguilla.
Evening: Dinner at 20 Knots
Assuming you are tired from a full day out (or not), you’ll want to take it easy. 20 Knots, described as laid-back luxury, is exactly the place to do so. This deluxe dining experience features live entertainment accompanied by endless stretches of sand and friendly staff who make you feel at home. On any day of the week, celebrate the flavours of fresh, locally sourced seafood while listening to the catchy tunes of live music performers.
Day 7: R & R
Morning: Breakfast at You Villa
Savor the morning of your last full day in paradise with a leisurely breakfast. Order a fresh fruit platter, hot johnny cakes, or eggs, and enjoy it on your private patio overlooking the ocean. Let the balmy breeze revitalize you as you take some time to replay those epic memories made during your stay.
Massage
Treat yourself to a spa day. If you are staying at CèBlue Luxury Villas, your personal concierge can arrange this service for you in the comfort of your villa. If this option is not available to you, book a massage, facial, or body treatment at one of the luxury resorts such as Thai House Spa on Zemi. Pamper yourself with treatments inspired by local ingredients like sea salt, coconut, and aloe vera, leaving you relaxed and rejuvenated.
Afternoon: Souvenir Shopping
When you’ve rested and are refreshed, make a quick stop at the local shops to pick up souvenirs. Look for handmade crafts, jewellery, and artwork that captures the essence of Anguilla. Anguilla Sands and Salts would be our first choice, as this is a truly special place. They offer unique keepsakes made on and from the island of Anguilla. Flavour-infused local sea salts for culinary use, as well as bath salts are among some of the unique gems sold here. To take this from a regular shopping trip to an incomparable experience, visit on a Martini Mondays, Wine down Wednesdays and Margarita Thursdays featuring their favourite salts tastings.
Evening: Dinner at Dolce Vita
For your final dinner, we suggest you dine somewhere that will leave a lasting impression, Dolce Vita Restaurant. Dolce Vita is a restaurant that serves phenomenal Italian meals. Food so decadent, you feel a little guilty treating yourself to their beautifully plated meals. Enjoy a glass or bottle from their extensive wine list, indulge in opulent desserts and experience their great service in a chic atmosphere next to a quiet bay dotted with boat lights in the distance. Return to your accommodation as stuffed as a Thanksgiving turkey and let the rhythmic sound of the waves lull you into a state of reminiscence as you drift away into the deepest sleep you’ve ever had.
Departure
We hope you enjoyed our summer vacation in Anguilla guide. Sadly, all good things must come to an end. As you head to the airport or ferry terminal, take one last look at the striking cerulean waters and picturesque sandy beaches. You’ll leave Anguilla feeling relaxed, refreshed, and with a trove of remarkable memories.
Anguilla offers a sublime summer vacation experience, melding luxury with the allure of island life. Whether you’re lounging on its world-famous beaches, exploring the rich culture, indulging in fine dining, or revelling in water sports and adventures, Anguilla has something for everyone. This 7-day itinerary is just a glimpse of what’s possible in this extraordinary Caribbean utopia, making it the ultimate destination for your next summer getaway. Reach out to us and book our studio penthouse at The Fountain Anguilla today! See you soon!