If you’re craving a Caribbean getaway that’s equal parts culture, excitement, and beachside bliss, look no further than Anguilla’s Summer Festival. Every year, the island comes alive in August with an explosion of color, music, boat races, pageantry, and island spirit. Whether you’re a carnival lover, beach bum, or curious traveler, the Anguilla Summer Festival offers something for everyone, and we’ve got the perfect spot for you to stay while soaking it all in. Here’s a rundown of the festival’s top events and why The Fountain Anguilla should be your island home base.
J’ouvert Morning: Dance Into the Day
The celebration kicks off at the crack of dawn with J’ouvert, one of the most anticipated street parties in the Caribbean. Starting around 5 AM, locals and visitors alike dance their way from The Valley to Sandy Ground to the sounds of live soca music. It’s messy, it’s joyful, and it ends with a massive beach party where the energy is absolutely electric. If you love the idea of sweating, laughing, and dancing your way into daylight, J’ouvert is a can’t-miss.
August Monday Beach Party & Boat Race
After you’ve survived J’ouvert (and trust us, that’s an accomplishment), keep the adrenaline going at the August Monday Beach Party. Held at Sandy Ground, this is the epicenter of fun. With DJs, food stalls, swimming, and dancing, the beach becomes a party zone. Around 1 PM, the traditional boat race begins. A beloved local sport where handmade sailboats cut across the ocean in a high-stakes race. It’s exciting, competitive, and completely Anguillian.
Miss Anguilla Pageant
Take a break from the beach and experience some glamour at the Miss Anguilla Pageant. Local young women showcase not only their beauty, but also their poise, talent, and intelligence in this elegant competition. It’s a powerful display of pride and empowerment, and the energy from the crowd is just as moving as the pageant itself.
Calypso Monarch Competition
If you appreciate the art of storytelling through song, the Calypso Monarch Competition is your night. Local artists take the stage at the Landsome Bowl Cultural Centre to deliver sharp, often humorous, and deeply cultural calypso performances. Lyrics touch on everything from politics to everyday island life, and the crowd doesn’t hold back when it comes to cheering on their favorite performer.
Eyes Wide Shut Beach Party
This early morning bash is one of the most buzzed-about events of the week. Eyes Wide Shut occurs at Sandy Ground and features performances from some of the region’s best artists. Think sunrise vibes, pumping music, and a lively crowd that just doesn’t quit. If you’re a party lover, this is your golden ticket.
Grand Parade of Troupes
One of the festival’s most colorful events, the Grand Parade of Troupes sees the streets of The Valley explode in music, feathers, and dancing. Different villages bring their best costume designs, choreography, and themes in a friendly competition that’s nothing short of dazzling. It’s an immersive look at Anguilla’s creative culture and community pride.
The Poker Run
Feeling adventurous? The Poker Run is a unique twist on island hopping. Boats make multiple stops around the island, each stop giving you a playing card. At the end, the best poker hand wins! But honestly, most people are in it for the thrill of the ride, the beach bar stops, and the ocean breeze. It’s fun, competitive, and a great way to see the coastline.
Champions of Champions Boat Race
The grand finale of the Summer Festival is the Champions of Champions Boat Race. Only the best crews compete, and locals gather to cheer on their favorites. The pride and excitement are palpable. It’s a high-energy send-off to a week full of unforgettable memories.
Where to Stay: The Fountain Anguilla
Between boat races and beach parties, you’ll need a place to recharge, and there’s no better place than The Fountain Anguilla. Located on the peaceful Shoal Bay Beach, this serene villa resort strikes the perfect balance between luxury and laid-back island living.
Modern, Comfortable Villas
Choose from studio, one-bedroom, or two-bedroom units, each offering Caribbean-inspired decor, a full kitchen, and a private balcony or patio. Whether you’re traveling solo, with friends, or as a couple, the space feels like your own slice of island paradise.
Shoal Bay Beach is one of the most stunning in Anguilla, and The Fountain sits right on its edge. Start your mornings with a swim or enjoy a quiet sunset walk after a day of festival fun.
The Fountain offers everything you need for a smooth, relaxing stay: high-speed internet, beach chairs, a tropical pool, and concierge service. It’s just a short drive from all the festival action, but far enough to enjoy peace and quiet when you want it.
An Unforgettable Escape for the Anguilla Summer Festival
Anguilla’s Summer Festival isn’t just a bunch of events, it’s a whole vibe that pulls you right into the heart and soul of the island. From the culture and energy to the music, beaches, and that unbeatable community spirit, it’s something you’ve really got to experience for yourself.
So go ahead and lock in your stay at The Fountain Anguilla, pack light (but cute), and get ready to soak up a summer you won’t stop talking about.
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.