From ancient Amerindian settlements and European colonization to its recent 1967 Revolution, holidays and festivals in Anguilla are centered on historical events. Its most spectacular celebration of culture is the Summer Festival, beginning August Monday at 5am with 'J' Ouvert Mornin', a daybreak jam through the streets to celebrate emancipation. Nearly a fortnight of dancing, competitions, fairs, costumes and parades colour the evenings. During the days, as with almost all of Anguilla's major holidays, the island is filled with the excitement of beach picnics and boat racing, Anguilla's national sport.

The yachting crowd gathers at the beautiful sheltered harbour of Road Bay annually to take part in the Anguilla Regatta, while all associated partying takes place at Sandy Ground beach nearby. Races in various classes take place over seven days, including the astonishing Battle of the Banks, which features 12-metre yachts from the neighbouring island St Maarten, Spinnaker classes and Open classes. This is the ideal time for competitive yachtsmen and enthusiastic or even indifferent spectator alike to enjoy the atmosphere of this great sailing festival and be charmed by Anguilla's legendary hospitality and friendliness. Many local vendors will provide party-goers with tempting barbecued treats and typical local dishes, while the sea front at Sandy Ground boasts a choice of great restaurants for the more sophisticated taste.

May 30th is celebrated as Anguilla Day. On this day in 1967 the repulsion of the Royal St. Kitts Police Force from the island took place. Britain intervened and a peacekeeping committee was established. Debates over Anguilla's succession continued to be negotiated for another decade until December 19, 1980, when Anguilla became a separate Dependent Territory with some measure of autonomy in Government. Again it is the island's passion for boat races that is flaunted as crowds build up at Round Bay to watch the five to seven-hour race around the island which, along with the Independence Day parade, commemorates the occasion. Later, parties right across the island carry on well into the night.

The island celebrates its wonderful musical heritage at two very different but equally enjoyable events. The Moonsplash Reggae Festival in March is a weekend of great reggae sounds with top performers descending on the beach at Bankie Banx's exclusive beach bar, Dune Preserve, Rendezvous Bay. The concerts will have you grooving to the beat, while the beach party laid on to top off a fantastic weekend has to be experienced. Moonsplash is the biggest and wildest festival of its kind on Anguilla. Towards the end of the year, the Tranquility Jazz Festival is hosted by the CuisinArt Resort and features some of the brightest contemporary jazz stars such as Patti Austin, Dee Dee Bridgewater and Christian Scott. Performances take place over a long weekend and culminate in a traditional free finale and a host of local and regional performers.