Events, Festivals and Exhibitions

Anguilla’s biggest party returns from 23 July – 13 August 2023. The Anguilla Summer Festival will turn the Caribbean island technicolour with music parades and boat races – topped off with great food to set the taste buds tingling.

The festival, or Carnival, allows visitors to immerse themselves in the culture of the island as locals celebrates their roots through music, food, art, dance and sailing.

The festival’s roots are found in traditional August Monday fairs and bazaars. On 1 August 1838 enslaved Africans in British colonies were freed of chattel slavery. The August Monday celebrations started in 1940 in Anguilla.

Anguilla Summer Festival 2023 Schedule

The 2023 Festival highlights are:

Late July 2023

Pageants, food festival and first Boat Racing

The Anguilla Summer Festival gets going in late July with pageants celebrating local talent and beauty, including the Miss Anguilla Swimsuit Competition, Talented Teen Competition and Prince & Princess Competition. The Home Grown Street Poker & Food Festival on 22 July is a party starter, and the Boat Racing gets underway with the Pioneers Weekend and Peter Perkins Boat Race on 29 & 30 July.

Thursday 3 August 2023

Opening Night & Light The Street Parade

The official opening night of the Anguilla Summer Festival will heat up the streets with a spectacular Light The Street Parade. The energy for 2023 will be electric as the brightly lit floats, event participants wearing glowing jewellery and carrying neon torches and colourful music events light up the night sky.

Saturday 5 August 2023

South Valley Community Street Festival Bacchanal Saturday

The South Valley Community Street Festival is a celebration of entertainment, art and culture, which keeps the community spirit alive! Patrons will discover a showcase of live music, DJ sets, local arts and crafts, and cultural food and drink.

Monday 7 August 2023

August Monday, J’ouvert, Caribbean Beach Party and Class A & B Boat Race

This day’s events are a highlight of the Anguilla Summer Festival as the combination of a street jam and beach party equals 24 hours of party time, attracting thousands of revellers to the island. J’ouvert, a street parade which begins in The Valley and ends in Sandy Ground, capitalises on the talents of local musicians and artists who compete for the title of ‘Road March Champion’. Then comes the Caribbean Beach Party and Boat Race, with local and international artists taking to the stage for more than 12 hours of solid partying on Sandy Ground beach.

Thursday 10 August 2023

Eyes Wide Shut

Termed “The Ultimate Day Break Fete”, Eyes Wide Shut takes place from 1am – 11am, as partygoers dance all night and watch the sun come up in the morning. The crowd will be hyped by performances from the biggest soca music stars in the world, this year including Nadia Batson, Patrice Roberts, Ricardo Drue, Terri Lyons, Barrie Hype, DJ Avalanche, Grand Masters & many more.

Friday 11 August 2023

Grand Parade Of Troupes

The Grand Parade of Troupes is all about vibrant, flamboyant, amazing displays of colour and highly detailed costumes as a number of troupes dance and celebrate on the streets of Anguilla’s capital, The Valley. The streets and vibe are electric, and the music can be heard for miles. Anyone is welcome to watch, or even join in the dancing. The troupes are formed from different villages on the island of Anguilla, and a panel of judges rate the troupes to find a winner.

Saturday 12 August 2023

Anguilla Poker Run & Leeward Islands Calypso Competition

This day will see the most anticipated nautical event of the summer, the Anguilla Poker Run, one of the newest Caribbean boat parties, with sizzling food, pumping music and high adrenaline. Hundreds of people will hit the high seas, beach-hopping to different events. Not only is this event a thrilling game on the sea, it’s also a chance to show off stylish swimwear, making a statement on and off the water. Later in the evening, the Leeward Island Calypso Competition is held at the Landsome Bowl. Calypso is a huge part of Anguillan culture, and this final event, which brings together calypso kings and queens from the Leeward Islands, is a must see.

Sunday 13 August 2023

Champ Of Champs Boat Race (Class A & B)

The very last day of Carnival is when the Champion of Champions boat race is held. The winner from each race during carnival week will compete in the final boat race of the year, to find out who will become the official Champion of Champions! Sandy Ground is packed with avid boat lovers and it is a fabulous closing to the Anguilla Summer Festival!

About Anguilla

Anguilla boasts 33 pristine white sand beaches, tempting turquoise waters and excellent restaurants. Relax, chill and do as little – or as much – as you like.

Flights to Anguilla

British Airways and  Virgin Atlantic fly to Antigua from the UK, from there it is a short flight transfer to Anguilla. Alternatively fly KLM/Air France via Amsterdam/Paris to St Maarten (SXM), and then it’s a short boat / flight hop. American Airlinesflies from Miami International Airport (MIA) to Anguilla.

Need more persuading? Read Arianna Stephen’s Anguilla Holidays for Needed Winter Sun. 

Holidays in Anguilla

For more tourist information, visit the official website: www.ivisitanguilla.com.