Offshore Sailing School

Plan your next sail vacation with the professionals

Offshore Sailing School Leopard 40 sailboat

About Offshore Sailing School


Offshore Sailing School has taught over 160,000 adults and families how to sail and powerboat for more than 59 years. Instruction is available for all skill levels at six resort locations in Florida and the British Virgin Islands. Olympian, America’s Cup Sailor, and National Sailing Hall of Fame inductee Steve Colgate designed the Colgate 26 keelboat specifically for teaching as its rigging and systems are relevant to larger cruising yachts. America’s #1 Sailing School® offers US Sailing certification, recognized by charter companies worldwide. The company’s fleet includes Colgate 26 sailboats, 40’-50’ cruising yachts, sailing and power catamarans. OFFSHORE High, a biography about Steve and Doris Colgate, was written by Herb McCormick, was published in October 2021.

Offshore Sailing School

Offshore Sailing School’s most popular course is Fast Track to Cruising® where students learn to sail on Saturday & Sunday aboard the Colgate 26, then live and learn Monday to Saturday aboard a cruising yacht or catamaran. Students earn three US Sailing certifications in a week, enabling them to skipper a boat up to 50’. The company also offers a Fast Track® Power Cruising certification course.

Offshore Sailing School graduates receive benefits such as, discounts on future courses, first time charters with The Moorings, and invitations to join fabulous Colgate Sailing Adventures® flotilla vacations. To sign up for Offshore Sailing’s e-newsletter with video sailing tips, special promotions, event, and industry news, call 888-454-7016 or email [email protected].

Offshore Sailing School also offers Women’s Weeks, Performance Race Week®, team building and leadership development sailing programs. Offshore Sailing’s ‘Tweens & Teens family sailing vacation package allows up to three children ages 7-17 to learn to sail for free with two paid adult tuitions. 

Retired and active military save 10% on five day+ courses.

Featured Story

In just one week, Offshore Sailing School can turn anyone into a confident sailor, ready to explore the world under sail.

There’s something primally enjoyable about the feeling of skirting across the water carried only by the power of wind, the boat beneath you responding to your touch on the helm and your tug on the jib sheet as you chase the horizon. Humans have done this for thousands of years, and it’s undeniably the most romantic way to see the world.

Offshore Sailing School has enabled more than 160,000 people in its 59 years in business to capture this feeling.


Boat Types:

Colgate 26 sailboats  

Cruising Yachts – Monohulls 44’-50’

Sailing Catamarans – 40’-50’

Power Catamarans – 37’-51’


Boat Lengths:


Ed, Charles, Andrea, Ryan Offshore Sailing School graduates
Greek Flotilla Day 1
Learning to sail on Scrub Island

Charter Types

Sailing School offers bareboat charter certification

offshore sailing school charter destinations

Offshore Sailing School locations:


Captiva Island, Florida  

Fort Myers Beach, Florida  

Cape Coral, Florida  

St. Petersburg, Florida  


Tortola, British Virgin Islands  

Scrub Island, British Virgin Islands 


Contact Us

Offshore Sailing School

16731 McGregor Blvd., Ste. 110  

Ft. Myers, Florida   

United States, 33908  

Phone: +1 (888) 454-7016   

Email: [email protected]     


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Special Offers

Cruising World readers will save 10% on sailing courses aboard

Colgate 26 sailboats, monohulls or sailing catamarans at four Florida resorts.

Enroll between September 1-30, 2022, for courses ending by December 17, 2022.

Mention: Cruising World 10% Savings. Retired and active military save 10% on five day+ courses, which may not be combined with any other discount.