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RSW Living Magazine

Set Sail for Adventure: Offshore Sailing School Teaches More Than Just Boating

Apr 20, 2022 07:11PM ● By BETH OLIVER

There is nothing like the freedom and sense of peace one feels when gliding through the Gulf of Mexico aboard a sleek sailboat. Steve and Doris Colgate’s Offshore Sailing School has taught more than 160,000 students to sail for going on 60 years. The company takes great pride in getting so many people to enjoy the engaging and fulfilling nature of the sailing and boating lifestyle. 

What is most rewarding for Offshore Sailing School employees is the impact that learning to sail has on so many lives. Grandparents return to take courses with their grandchildren, teaching three generations to enjoy quality time on the water. They all put down their electronic devices and focus on having fun. Family members and friends are eager to learn a new skill and share an activity for years to come. Solo sailors and couples take one course, then another, sending the Colgates their thanks, along with photos and comments on their new “love” of sailing. Becoming competent and confident sailors and boaters in just one week amazes these students. 

Offshore Sailing School has operated out of South Seas Island Resort on Captiva since 1975. The company also teaches its courses locally at the Pink Shell Beach Resort & Marina on Fort Myers Beach and the Westin Cape Coral Resort. It partners with the Downtown Hampton Inn & Suites in St. Petersburg, Florida, and has two locations in the British Virgin Islands. 

 The school offers a full range of sailing courses and experiences as part of a resort vacation package: from basic learning to sail, to performance sailing courses and special racing events, to learning to bareboat charter aboard 40- to 50-foot monohulls, sailing and power catamarans. Experienced sailors may progress into advanced navigation and passage-making courses. For resort guests who want just a “taste of sailing,” there are two-hour lessons.  

Offshore Sailing School routinely offers “women’s weeks” with the company’s Fast Track to Live-aboard Cruising courses. These are exclusively for up to four women living and learning together for one week aboard a yacht, earning three U.S. sailing certifications to skipper boats up to 50 feet.  

There are also family sailing packages available at South Seas and Pink Shell. With the Tweens & Teens Learn Free package, up to three children ages 7-17 learn for free with two adults. This three-day course is part of a five-night resort vacation package, providing a good opportunity for family bonding time aboard a Colgate 26 sailboat. The fourth and fifth days are open for students to experience the many resort amenities and enjoy the area’s activities—swimming, paddle boarding, kayaking, visiting wildlife parks and cultural sites, shelling, shopping, and dining.  

Most of the courses are taught aboard the Colgate 26, designed by Steve Colgate with naval architect Jim Taylor. The high-performance keel boats are used for training by the U.S. Navy and Coast Guard. 

For group getaways, company incentive programs, or other group get-togethers, the company offers unique team building and regatta events. 

The Colgates created the concept of sailing flotilla vacations and have personally hosted more than 100 sailing vacations for Offshore Sailing School graduates and guests in exotic ports such as Tonga, Tahiti, Spain, the Greek islands, Italy, and destinations in the U.S., along with many islands in the Caribbean. Colgate Sailing Adventures in 2022 will sail in St. Martin, Croatia, the Seychelles, Thailand, and the British Virgin Islands.  

For more information, call Offshore Sailing School at 888-454-7015 or 239-454-1700; email [email protected]; or visit Offshore High, a biography about the Colgates and their school, by Herb McCormick, was published by Seapoint Books in 2021. 


Beth Oliver is VP, director of sales and marketing for Offshore Sailing School.