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Caribbean Courses

Join us for the best sailing education and winter holiday available.

We cover the same content as our popular Boston courses - only with white sand beaches, turquoise waters, and trade winds. 

ASA 104

Starting from Tortola, the cruising area will include the surrounding waters in the British Virgins Islands. Gain the fundamental skills needed to cruise and charter successfully on this 6-day course. This course will prepare you for a Cruising 30 or 35 membership or for bareboat chartering.

This course includes entering unfamiliar harbors, anchoring, sail handling, dinghy use and more. We cover the mechanical and electrical systems of a full-size cruising boat, the navigation required for sailing in coastal waters, and docking under power.

The course is structured so you can fly in on the first day and out on the last day. No need for a hotel! The course fee covers all food and drink on board. 


No offerings for 2022 season


Advanced Course or equivalent experience

Text Book

ASA's Bareboat Cruising Made Easy (included in course fee)


ASA 104 Bareboat Cruising

Prepares you for 

Cruising 30 or 35 Membership, Chartering in the Caribbean


The course fee covers all food and drink on board. *Discounts offered for students who have already enrolled in a macro program or have a current membership. Inquire with the office.

At least three students per week are required to run each course. Do not buy flights until the course is confirmed by the office.  

Sun Odyssey 449

Course Documents

Cancellation and Rescheduling Policies



Contact the Boston Sailing Center office by phone 617-227-4198 or email This email address is being protected from spambots. You need JavaScript enabled to view it. and an office manager would be happy to assist you.