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.
