Manhattan Caribbean Week


Next Event: January 23 – 31, 2021 – This time it will be a full 8 days!

Boats, Skippers & Crew – 2020
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 “Manhattan 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!


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 Manhattan Caribbean Week today!


Manhattan Caribbean Week 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 and other companies.


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, Manhattan Caribbean Week 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.


Manhattan Caribbean Week begins on Saturday in the BVIs 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 charter boats on Saturday evening. Then on Sunday, we push off for a week of sailing adventure.

By Monday afternoon, we end up in North Sound and sailors start to loosen up. This is where we hold the first Pop-Up Boat Party. These are one hour events when all teams gather on a single boat to mix and meet the other sailors.

On Tuesday, we hold an incredible bonfire party on a deserted sandy beach. As the evening gathers steam, look out for our exclusive “Ring of Fire!”

On Wednesday, we visit one of our favorite islands, Anegada which is located 12 miles 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. On this evening, we hold the famous Appetizer Competition which is followed by the Skipper Appreciation Lobster Dinner at Neptune’s Treasure.

New Caribbean Skippers are also inducted this evening by King Neptune. The late night party continues at Potters where you can dance barefoot in the sand and compete in the limbo.



On Thursday, it is on to Jost Van Dyke where we visit beautiful White Bay, home of the world-famous Soggy Dollar Bar. Or if you want to go somewhere more quiet, you can visit Ivan’s Stress Free Bar. In the evening, we gather at Foxy’s for dancing.

Friday brings us to the great snorkeling at Norman Island where you can visit the Caves or stop by the Indians. We will test your boat’s teamwork during the dinghy race.


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 afat Willie T’s are presented with “The Royal Order of De Caribbean Regatta” medals. This is a secret society and we cannot tell you how you can earn the medal. All we know is what happens in the Caribbean, stays in the Caribbean.


On the final Saturday of Manhattan Caribbean Week, we hold race against the Royal BVI Yacht Club and the West End Yacht Club. The race finishes off Soper’s Hole and this evening, everyone is invited aboard Arabella for the final night party.

Then on Sunday, we sail our charter boats back to their dock, hop on ferries and planes and fly back home, with an incredible Caribbean tan and a lifetime of memories.

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

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

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