Caribbean Week


In 2019, there will be 2 events:
BVIs: January 26 – February 2, 2019
St Maarten & St Barts: March 9 – March 16, 2019

Boats, Skippers & Crew – 2019
Registration Form

Every winter, Manhattan Yacht Club teams up with Manhattan Sailing School to organize an incredible week of sailing in the Caribbean.  This event is known as “Caribbean Week” and it will be the greatest vacation of your life!

We go in the deepest and darkest part of the winter when we really need the warmth and sunshine of the Caribbean!

The first event to the BVIs at the end of January will focus on teaching and education. The BVIs is the best place to begin your Caribbean sailing adventures. School students and people who have not experienced the Caribbean before should begin in the BVIs.

The second event at the beginning of March will focus on MYC Members and people who are more experienced Caribbean sailors. The conditions in St Maarten & St Barts will include more open ocean and longer distances.


Have you ever dreamed of sailing in the Caribbean?  Would you like to see beautiful turquoise waters, walk barefoot on a white sandy beaches and feel the warm trade winds caress your face?  Make your dreams come true.  Sign up for Caribbean Week today!


De Caribbean Regatta takes place in the British Virgin Islands.  The BVIs are considered the best cruising grounds in the world.  There are consistent trade winds and warm temperatures all winter.  The islands are close together so it is just a few hours to sail from harbor to harbor.  And the islands are focused on sailing tourism so you are welcomed everywhere.

Participants in the regatta hop on planes and fly down to the BVIs.  Then we board charter boats from the Moorings, Sunsail and Footloose.


Every morning, we raise our anchors, hoist the sails and head off to a new destination.  Then we spend the afternoon sun bathing, snorkeling, visiting a beach, reading a book or just plain relaxing.  Every evening, the regatta sailors gather for a party.  You will meet lots of fun people, sail and swim every day and have an incredible voyage of discovery.


The charter boats in our flotilla are skippered by a Member or a sailing school instructor.  Members and students are invited to sign up for spots onboard these charter boats.  You can sign up by yourself or bring a friend.  All cabins are double occupancy and if you sign up by yourself, we will try to connect you with a cabin mate.


In the fall, we organize several “Pump Up Parties” where Members, students and skippers can meet and form teams.  Every team has its own name and “boat flag.”

Caribbean Week begins in Road Town on Tortola.  You can get there by flying to St Thomas and taking a ferry, or flying to Beef Island on Tortola.  Sailors arrive on Friday or Saturday and we board the small charter boats on Saturday evening and Arabella on Sunday morning.  Then on Sunday, we push off for a week of sailing adventure.

By day 2 of the regatta, sailors are starting to loosen up and we begin having evening “Boat Parties.”  These are one hour events when all teams gather on a single boat to mix and meet the other sailors.

One of the great stops along the way is North Sound.  This is where we the “Beach Ring of Fire Party” on the deserted sand of Prickley Pear Island.




One of our favorite islands is Anegada, just north of Virgin Gorda.  Because Anegada is a flat coral island, you will see turquoise water like never before!  You can relax for the afternoon at Cow Wreck Bay.  In the evening on Anegada, we hold the Appetizer Competition as well as the Skipper Appreciation Dinner at Neptune’s Treasure.  The late night party continues at Potters where you can dance in the sand.



The final evening of the regatta brings everyone to Norman Island.  This is home of the world famous “Willie Ts” floating bar.  The final competition of the regatta is the dinghy race.  It brings out the competitive nature in many of the sailors!


After the dinghy race, there is one last Boat Party and then it is on to Willie Ts for dancing until the early morning hours.  Those sailors who fully embrace the Caribbean Spirit after the week of sailing are presented with “The Royal Order of De Caribbean Regatta” medals.   This is a secret society and we can not tell you how you earn the medal.  What happens in the Caribbean, stays in the Caribbean.


We hope you will join us for the next Caribbean Week.  It will be the greatest vacation of your life!

For more information, call Manhattan Yacht Club at 212-786-3323 or email

We can also email you a PowerPoint which explains the regatta.  You can share this with any friends you want to join you.

Registration Form

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