Anguilla Experience, Cap Juluca Experience

In the Caribbean Everyone Knows a Little Something About Sailing: Regattas 101

boat racing in the caribbean

Sailing and the Caribbean go together like cheese and fine wine. Hundreds of beautiful islands surrounded by sparkling turquoise waters makes for a fine setting to cruise around on a sailboat.

Sailing in the Caribbean originated from a place of need, but has since evolved into an enjoyable leisure activity that has become the most celebrated sport throughout much of the region. On Anguilla in particular, sailing is the national sport, and sailing events arouse as much excitement and anticipation as the Super Bowl!

Sailing yachts regatta. Series yachts and shipsA regatta is the name of a sailboat race, and it is one of the most exciting events to attend. The Anguilla sailing association literally has a “100% Fun Guarantee” on their website.

As far as is known, regattas began around 1274 in Europe. The professional watermen that worked on the Thames River in London, providing ferry and taxi services, would compete among one another, drawing bigger crowds each time. The sport became immensely popular and began to spread throughout Europe, and then eventually to North America and the Caribbean.

The excitement and thrill continues to draw folks in year after year.

Boat Racing in the Caribbean

To give you a little taste of a regatta, here are the what, where, why, when, and how’s:

What it is: Regatta means “a series of boat races.” At the culmination of the races, the finishing scores of each boat are totaled, similar to golf. The competitor with the lowest score is the winner. Many times regattas turn into all-day events, with plenty of eating, drinking, and socializing.

boat racing in the caribbeanWhere the Races Take Place: On the water. Naturally each specific regatta takes place at a specific location. In the case of Anguilla, Simpson Bay serves as the starting point for many of the regattas.

When: This all depends on which event you want to attend, Anguilla has multiple regattas a year, but the next one will be Friday May 8th!

Why: Because it’s so fun! Whether you’re on the boat or watching the boats, everyone has a great time. It’s an excuse to be outside, taking in the sun, gazing upon the sea, and drinking plenty of fine wines and champagne.

How: How does a regatta work? Well, most of the boats that compete are locally built and designed, with their own names, and plenty of logos from sponsors printed on their sails. As a spectator, all you have to do is arrive, drink, eat, and be merry.

You may also enjoy: Sailing in Anguilla – The Undisputed Fever for Boat Racing

boat racing in the caribbeanConvinced this might be an event you’d like to attend? Really, what could be better than relaxing on an idyllic island, being surrounded by pristine and natural beauty, noshing on delectable cuisine, sipping on vivacious cocktails, all the while gazing upon racing sailboats? Few experiences come close. Anguilla is a magnificent island to be on year-round, but it’s even more enticing when a regatta is underway.

Related: Here on Anguilla, We Embrace a Flip Flop State of Mind

Keep in mind that Anguilla is an island of the utmost luxury, and the villas and hotels get booked well in advance. Just be sure to plan ahead so you don’t miss out on premier accommodations during the excitement. Cap Juluca Resort is an Anguilla institution, set on it’s own mile-long private beach – Maundays Bay, and it offers 15 villas featuring 69 guest rooms.

Hop on a jet, yacht, or any mode of transportation that suits you, and visit Anguilla during one of the regatta events and you’ll be amazed at how sweet life can be. You may even find yourself taking a sailing lesson or two afterwards!


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