Alumni Flotilla Cruise 2019


Some of you may have heard me say this before, pictures don’t do the Caribbean justice. It seems like every time you tack another breathtaking vista appears. We have been taking groups to the Caribbean for over 20 years, and look forward to it.

Join flotilla for an exciting NEW bareboat cruising adventure “down island” with J World Annapolis and the Chesapeake Boating Club.  If I was asked what is my favorite group of islands in the Caribbean my immediate answer would be the Leeward Islands. They offer a unique snapshot of all the different cultures that have come and gone throughout the history of the Caribbean. The Leeward Islands boast some of the most stunning scenery and anchorages with plenty of beautiful beaches, historic towns and national parks to explore, beaches for swimming and colorful underwater wildlife for snorkeling.
We have chartered four boats, two Sunsail 444 catamarans and two Sunsail 51.4 monohulls.  Each boat will have four private cabins with room for two.  You will be grouped together with other alumni aboard our fleet of charter boats. Limited experience is not a problem! Lesser-experienced sailors will be placed onboard a boat with a qualified skipper. All alumni and their immediate friends and family are invited to join us!

We will begin our Flotilla in Marigot Bay on St. Martin, tentatively visiting St. Barth, St. Eustatius, Anguilla and where ever else the wind blows us.

Tuition: $3995 per cabin. The price includes all boat charter-related expenses, partial provisioning, cruising taxes and mooring fees and our custom flotilla T shirt! You should budget additionally for airfare, meals ashore, alcohol, and any shore-side transportation. Click here for trip details.
The US Sailing Bareboat Cruising course will also be offered to interested sailors at an additional cost.  Please note that the US Sailing Basic Keelboat and Basic Cruising certifications are pre-requisites for earning a Bareboat certification.
Space is Limited!  Call us at (410) 280-2040 or email us at for more details and to register.


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