Sail Fast. Live Slow.

Take a break from your daily routine for a month or two and load up on adrenaline while you island hop through the 2016 Caribbean Regatta Series.

“Fifteen Men on the dead man’s Chest,
Yo-ho-ho and a bottle of rum!”

Sailboats are known for being a Zen place to be at peace in calm waters… this is not that kind of sailing trip! The Caribbean Regattas are international events where competitive sailors from all over the world find their way to the tropics and leave their best on the racecourse. Regardless of how you chose to participate, as a spectator or as crew, the fun, carnival-like environment that arises at these events will undoubtedly crate unique lifelong memories.

First stop, the beautiful island of St. Maarten for the St. Maarten Heineken Regatta. March 3-6 will mark the 36th Anniversary of one of the biggest races in the Caribbean. After the race ends you will be able to enjoy great food and ice cold refreshments with your feet in the sand, while listening to local, regional and international music. On a leisure day make sure you take a ride around this small yet culturally diverse gem. St. Maarten, or Saint Martin, depending on whom you ask and what side of the island you are on, was peacefully divided between Holland and France, and today is the smallest landmass in the world to be shared by two sovereign nations.

St. Thomas’ International Regatta is a few weeks later on March 25-27 and is only a two and a half hour flight away from South Florida. Any sailor will tell you that this race is the “Crown Jewel of the Caribbean” because St. Thomas is the place to compete with top sailors in the world’s finest racing conditions. This US Virgin Island’s fresh breeze, warm waters, shopping, food and music fests are pretty amazing as well. You will have no problem finding something for everyone to enjoy.


Not ready to go home yet? Hop on the ferry to Tortola, the largest of the British Virgin Islands, for the 45th BVI Spring Regatta and Sailing Festival. This week long boater’s fest starts on March 28th and concludes with the BVI Spring Regatta, April 1-3. Three days of intense races with courses that stretch along the sheltered Sir Francis Drake Channel, home of “Treasure Island” and on the south side, a small cay named “Dead Man’s Chest,” protagonist of the famous sea shanty about Blackbeard marooning 15 men on the cay with nothing but a bottle of rum…

You have a few days to recover from your drunken pirate endeavors before the 7th edition of Les Voiles de Saint Barth kicks off in Gustavia, the capital of St. Barthélemy, from April 11-16. Although it is the “youngest” of the Caribbean’s major sailing meets, no fewer than 80 boats and 1,000 sailors are expected to compete at this unique international competitive gathering just southeast of St. Maarten.

The sailing series ends with the 49th Antigua Sailing Week from April 23-29, 2016. Sailboats up to more than 100 feet in length compete throughout the week and an Overall Winner is announced on Friday along with those of the multiple racing categories. So be sure to take in your last bit of adrenaline and island fun as participants celebrate with much enthusiasm before heading back to reality.