Offshore Sailing School

Plan your next sail vacation with the professionals

About Offshore Sailing School

Offshore Sailing School has taught over 160,000 adults and families how to sail and powerboat for more than 58 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’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, 1st 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

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.


Boat Types:

  • Colgate 26 sailboats  
  • Cruising Yachts – Monohulls 44’-50’
  • Sailing Catamarans – 40’-50’
  • Power Catamarans – 37’-51’

Boat Lengths:

  • 26’-51’

Learn to Sail with America's #1 Sailing School


Charter Types

Sailing School offers bareboat charter certification

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   



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Special Offers

Cruising World readers will save 10% on sailing courses aboard

Colgate 26 sailboats, monohulls or power catamaran at four Florida resorts.

Enroll between September 1-30, 2021, for courses ending by December 18, 2021.

Mention: Cruising World 10% Savings. Retired and active military save 10% on five day+ courses.

Ready to Plan a Charter?