Anguilla Summer Festival Boat Racing is held on the first Monday of August. It first started on a Monday of August in 1940 and since then it is celebrated officially with boat racing. Boat racing is a very popular sport and it is clubbed with the carnival which is known as Summer Festival. The boat racing is the best pastime sport for Anguillians unlike cricket which is a national sport for the other Anglophile Caribbean islands.
The Anguillians lived a hard life and depended a lot on the sea for their livelihood. It is from here that the art of boat racing and the love for the sea developed. The Anguillians could not find any means of survival on land and therefore their dependence on sea grew. It was thus the experience of voyages and frequent traveling to Dominican Republic that the art of boat racing came into existence.
Even today, there are many racing boats that are named after the cargo sloops from the 19th century which is a mark of respect to these that ploughed the seas of the western and southern Caribbean. Every boat is a legend and has its own story.
There are many hotels and guest houses where they offer special rates and packages for people who are keen to be a part of boat racing and the carnival. Boat racing is a day activity during the Anguilla Summer Festival. The Meads Bay and the Sandy Ground are the two best venues for boat racing. The live music, white sand and clear water makes it all for thousands of fans, picnickers and enthusiasts to come and cheer the boat racers. The different types of foods and beverages that are served and the pleasure boat rides, you have it all at the Anguilla Summer Festival.
The boat racers are divided into three categories- A, B and C. In this group A has a 28 ft boat in length which can accommodate 14 men with hunks of iron, sandbags and pounds of ballast. They are the most popular group and these are the only traditional sail boats that one can find.