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. See you soon!
