Anguilla Summer Festival — First Monday of August “August Monday”

The last of the famous festivals in Anguilla is Anguilla Summer Festival. Anguilla Summer Festival began in 1940 as a boat race and has since evolved into the multi-day Caribbean "Carnival" and never-ending beach parties that it is today. The bay ("Road Bay"), which is held on the beach in Sandy Ground Village, attracts hundreds of people and boats from all over the Caribbean, not just Anguilla. The events begin at the end of July, but the main boat race and party take place on August Monday, which is the first Monday of August each year.

Private and party boats form a floating parking lot for the best viewing spot, and residents and tourists alike celebrate with music, dancing, and food, while crewed boats race around the island at breakneck speeds for bragging rights, eligibility for other future races, and the coveted title of champion.

Other events leading up to the main event include pageants, parades, fireworks, concerts, contests, and plenty of partying. Carnival is a spectacular place, but if you want quiet, uncrowded beaches, you should go at a different time of year. Because August Monday is a federal holiday, offices and many businesses (including grocery stores) are closed.

Takes place: on the first Monday of August