TBA - Events are usually held in July and August.
The Anguilla Summer Festival is celebrated on the Caribbean island of Anguilla.
Anguilla Summer Festival is the island’s carnival, held every year around August Monday — the first Monday in August — and running for roughly a week either side. Unlike most Caribbean carnivals, its centrepiece is not a parade but a boat race: hand-built wooden sloops, sailed by island crews, contested from the beach.
That distinction goes back to emancipation. August Monday marks the end of slavery across the British Caribbean, and the day was claimed early on as a holiday for gathering, feasting, and racing the same working sloops that fished these waters. Boat racing became Anguilla’s national sport, and the festival grew outward from it — adding calypso, pageants, troupes, and beach parties without ever displacing the boats. To understand what this festival means to Anguillians, you have to understand that the boats came first.
Expect a festival that lives on the water as much as on the road. Boat racing is Anguilla’s national sport, and it anchors the whole two weeks — villages back their own boats, crowds line the sand, and the rivalries are personal. Around the races sit J’Ouvert, the Grand Parade, beach parties, and pageant nights at the Landsome Bowl.
Marvel at the grace and elegance of contestants vying for titles in beauty pageants, where participants showcase their poise, talent, and charisma.
Anguilla’s national sport: fast-paced boat-racing competition across the sea routes — a major draw for locals & visitors alike. Witness exhilarating boat races featuring locally crafted vessels.
Groove to the rhythm of soca, reggae, and other Caribbean music genres performed by local and international artists, creating an electrifying atmosphere throughout the festival.
Indulge in delicious Caribbean cuisine and refreshing tropical drinks offered by local vendors, featuring specialties such as grilled seafood, jerk chicken, and fruity cocktails.
Experience the vibrant and colorful street parades filled with elaborate costumes, infectious music, and energetic dance performances, celebrating the island's culture and traditions.
Immerse yourself in the vibrant energy and infectious spirit of Anguilla's Summer Festival, creating lasting memories of joy, camaraderie, and cultural appreciation.
Date: TBA — expected in July and August 2027
Location: The Valley, Anguilla
Time: Various times
Anguilla Summer Festival pairs carnival with the island's national sport, combining boat racing, calypso competitions, pageants and a costumed road parade. The official 2027 dates, event venues and full programme have not yet been published. We'll update this page as soon as the organisers announce the details.
Note: Changes to the schedule are beyond our control, so please check for updates before finalizing travel plans.
Anguilla is easy to reach whether you’re coming from elsewhere in the Caribbean, North America, or internationally.
Ready to lock in your flights? Use the search tool above to compare fares and find the best deal for your Carnival trip.
The best areas to stay are near The Valley, Sandy Ground, Shoal Bay, and Meads Bay — all close to Summer Festival events and Anguilla’s legendary beaches.
Use the above map to find and book stays near the Carnival parade route!
Getting around Anguilla during Summer Festival is easy thanks to the island’s small size and short travel times between main event areas.
Explore Sandy Ground Village for beach bars and live music, take a sail to Prickly Pear Cays for a sun-soaked escape, or unwind at Shoal Bay East, one of the Caribbean’s most stunning stretches of sand. Foodies can indulge in fresh lobster at Scilly Cay or enjoy upscale dining at Veya Restaurant. When the night cools, grab a rum punch and catch local bands jamming under the stars.
We’ve gathered some of our most useful Carnival travel blogs to help you plan for Anguilla Summer Festival and other Caribbean festivals:
