Moonsplash Music Festival - March 
Hosted by home-grown calypsonian and musician Bankie Banx over the full moon weekend in March, an easy-going festival of Caribbean music with leading reggae artists - savor traditional reggae music and cocktails at his bar, the Dune Preserve beach bar on Rendezvous Bay.

The Festival Del Mar, Island Harbour - Easter weekend
Festival Del Mar celebrates all things of the sea, with traditional cooking and culinary competitions (seafood recipes only!), swimming races, fishing tournaments, boat racing and more. 

Anguilla Day - May 30
Anguilla Day commemorates the island’s independence from the associated statehood of St. Christopher-Nevis-Anguilla, formed in February of 1967 by British Parliaments. It is an excellent time to visit the island.  It is a day of joyful celebration for Anguillans, but also for visitors. 

Carnival - August
Anguilla's most colorful annual festival is Carnival, held jointly under the auspices of the Ministries of Culture and Tourism. The festival begins on the Thursday before the first Monday in August and lasts 10 days. The festival also features spectacular parades with floats, elaborately costumed dancers, terrific bands, and lots of competitions, including the very popular Miss Anguilla contest. Carnival harks back to Emancipation Day, or "August Monday," in 1834, when enslaved Africans all throughout the British colonies were freed.

Anguilla Regatta - Early May
Anguilla Regatta (www.anguillaregatta.com) features competitive races over a three-day weekend, with free entertainment and barbecues every night. 

Tranquility Jazz Festival - November
Tranquility Jazz Festival (www.anguillajazz.org), held in the second week of November, is becoming one of the top Jazz events in the Caribbean, with over four days of events, artists perform at venues all around the island. Listen to the sounds of world class Jazz as you relax on the beach or sip on a long cool drink.