Alumni Flotilla Cruise 2024

Pictures don’t do the Caribbean justice. It seems like every time you tack, another breathtaking vista appears.

Brought to you by J World Annapolis and the Chesapeake Boating Club, join us in February 2024 for the adventure of a lifetime – The British Virgin Islands.

Come Sail with us among some of our favorite island and anchorages including Jost van Dyke, Virgin Gorda, Anegada and more.  The BVI’s offer a unique blend of stunning scenery, easy logistics, modern amenities as well as island charm and solitude.  If you have not sailed on a flotilla with us before, are new to bareboat cruising, or simply love these islands like we do, this is the ideal trip for you.  We plan to have 3-4 boats in the 41 – 50 foot size range.  Each boat will have three or more private double cabins, so you can bring your significant other with you and have a cabin to yourselves!

Call the office for pricing and cabin availability. 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.
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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