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By Larry Benedict

The daydreams of exploring the Caribbean or the coastal waterways of the Americas begin the moment the days turn chilly, and no winter daydream is more appealing than setting a course for an unknown tropical island across a glittering sea. Fulfillment of this wishful thinking however requires a certain proficiency in handling a boat. If the fact that your can’t tell a sheet from a gudgeon is all that’s holding you back, we have assembled a list of sailing schools that provide instruction as well as rental craft tailored to the experience of the individual. They can turn your daydream into a reality in much less time than you think.

Top Photo: Offshore Sailing School
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J-WORLD - The Performance Sailing School - Annapolis MD, Newport RI, Key West FL, San Diego CA

J-World was named best sailing school in the US by Practical Sailor Magazine and was attended by Chelsea Clinton in 1994. They have a new World-Wide Certification Program for beginners as well as experienced cruisers and are sanctioned for charter by the U.S. Sailing Association; (designated by Congress as the official governing body of sailing).

“A lot of our students come to get bareboat-charter certified so they will not have to pay a captain,” says John Alofson, President of J-World, “They want the confidence to sail the boat on their own and often have the dream of one day chartering a boat in the Caribbean or other exotic vacation destination.”

Cruising courses are available at three different levels, beginners, intermediates and a live-aboard course for the more experienced sailors. At J World students receive full days of sailing instruction.

Sampling of Courses Available:

To learn more about schedules, courses offered, and student requirements contact J-World at:

Despite the large number of charter boats available in the Caribbean, there are few charter operations that offer instruction from scratch. At The Bitter End Yacht Club on Virgin Gorda in the British Virgin Islands, the range of boats starts with a sailboard and goes up to a Freedom 30 (footer). Most of the sailing is day-sailing with an instructor and accommodations are available in the villas resort, (if you choose not to sleep aboard the yacht). According to Conde Nast Magazine, this is one of the most comprehensive sailing programs in the Caribbean.

Sampling of Courses Available:

More information about Bitter End Yacht Club and the Nick Trotter Sailing School is available through the central reservation and sales office:


The Santa Barbara Sailing Center is one of the largest accredited sailing schools in the nation and issues both ASA (American Sailing Association) and US SAILING student certification. 40 boats and a large staff of impressively qualified instructors prepare the graduate to sail anywhere in the world.

Sampling of Courses Offered:

For Information on Boat Rentals, Club Membership and Instructional Charters contact:
BLUE WATER SAILING SCHOOL - Ft Lauderdale FL, Other Locations

An American Sailing Association Sailing Facility
Advanced Coastal Cruising, Celestial Navigation, Offshore Passages

Offers all levels of ASA Certification - has a unique four-to-five week Mini-Transatlantic course from Florida to Bermuda for experienced sailors. The top course offered by the school is the “Transatlantic Crossing.” This is the ultimate achievement for any seasoned sailor: a Transatlantic crossing via Bermuda and the Azores Islands with landfall in Portugal or the return to Florida via Portugal, the Madeira Island, the canary Islands and the West Indies. Your next step will be to sail around the world in your own boat. . .

For Information contact:

OCSC - San Francisco Bay Sailing - San Francisco CA - Web Site

Keelboat Certification System - Begin with a solid foundation of sailing instruction.

US Sailing offers Certified Instructors, instructional materials developed by US Sailing, US Sailing Certification, US Sailing membership.

Sampling of Courses Offered:

For Additional Information: Visit their Web Site
Steve and Doris Colgate’s OFFSHORE SAILING SCHOOL - Captiva Island FL, St Petersburg FL, Newport RI, Tortola BVI

“The Offshore Sailing School makes skippers out of hard core urbanites in less than a week.” -- New York Magazine

The Offshore Sailing School offers an outstanding array of classes, programs cruises and events. Along with basic, intermediate and advanced courses for keelboat and cruising sailors, they include the following:

To learn more about this smorgasbord of sailing opportunities and their locations including Captiva Island, Florida; Newport, Rhode Island; St Petersburg, Florida and Tortola British Virgin Islands, contact Offshore Sailing school or visit their Web site.
ANNAPOLIS SAILING SCHOOL - Annapolis MD, St. Petersburg FL, and St. Croix, US Virgin Islands

America’s Oldest and Largest Sailing School offering:

A broad range of classes are offered for every level of proficiency. Basic Sailing weekend classes begin at $225 per person and 5 Cruising course aboard the Morgan 44 begins at $1,000 and is based on your grad or non-grad level and cabin location (dbl occupancy with private cabins available. Among a multitude of other courses Annapolis offers “Kid Ship” a program designed for children who are learning to sail.

Annapolis Sailing school offers a Celestial Navigation Home Study Course for $210.

To borrow a video from the Annapolis sailing School library send $25 (refundable deposit per video) to the address listed below.

All prices are subject to change and those interested in complete information should call (800) 638-9192

WOMANSHIP - Fort Myers FL, Biscayne Bay FL, Tortola BVI

Sailing taught to women by women. Womanship’s motto is “Nobody Yells” and for those who have crewed with overbearing skippers it carries great appeal. Offered are live-aboard learning cruises for all levels of proficiency. Cruises originate from Fort Meyers Florida, Biscayne Bay, Florida and Tortola British Virgin Islands.

Sail on 30-45 foot yachts with rates ranging from $464 to $1,254.

For more information contact:

Next month Bareboat Charters, a list of charter services for the students who made the grade and are ready to strike out on their own.

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