“HAPPY HOLISAILS”students learning to bareboat charter in St. Pete

We’re making this season brighter with 15% savings on most courses, all locations, for solos and more!

Enroll in new sailing or power cruising course between December 1 and 22, 2023, at 5:00 p.m. ET, and save 15% when you complete your course in 2024. Students enrolling between these dates will receive a surprise in their confirmation package too!

Offer valid on the following courses:

*Cruising courses require minimum of two enrolled so solos will be placed with other confirmed students.

We teach minimum age 7 in Learn to Sail courses with family, and minimum age 12 in cruising courses with family. HAPPY HOLISAILS promotion excludes value-priced Family Learn to Sail, Family Cruising, Navigation, and Passage Making courses. HAPPY HOLISAILS discount may not be combined with Military nor Offshore Sailing School Graduate discount.

Colgate Sailing Adventures® flotilla trips are discounted separately for Offshore Sailing School graduates with US Sailing Bareboat Cruising certification, and an IPC.

Call 888-454-7015 for more details.


It’s not too soon to plan spring break and summer 2024 vacations!

Fast Track® to Live Aboard Cruising Course for families, available at our four vacation destinations, ‘Tween Waters Island Resort & Spa on Captiva Island, Florida, the Downtown Hampton Inn & Suites in St. Petersburg, Florida, Stock Island Yacht Club & Marina in Key West, Florida (own accommodations), and Scrub Island Resort, Spa & Marina in the British Virgin Islands. In this specially-priced learning vacation package, a family of 4* comprised of two adults and two family kids, minimum age 12 and maximum age of 25 will learn to sail aboard a Colgate 26 for two days. On the third day, move aboard the yacht, either a monohull or catamaran, while you learn to handle a big boat for the remainder of the week. At the end of one week, you will be certified to skipper a yacht up to 50′, and you may choose to apply for your International Proficiency Certificate if you wish to charter in Mediterranean countries. Perfect opportunity to reunite family members, learn to bareboat charter together, and enjoy countless boating vacations in the future! Call 888-454-7015 for course availability.

*Fifth family child between age 12 and 25 may be added for additional fee. May not be combined with any other offer nor promotional discount.


Save $300* person when you enroll in another course or join one of our flotilla trips

Join a hosted sailing vacation and see the world under sail.

The best savings on Colgate Sailing Adventures® flotillas are for Offshore Sailing School graduates with US Sailing Bareboat Cruising Certification.

*Savings may vary and increase for certain flotilla trips, and for those with Bareboat Cruising certification, the International Proficiency Certificate and willling to Skipper a yacht if asked.

Once you earn your Bareboat Cruising certification in this course, you may apply for the International Proficiency Certificate which is required to charter a yacht in certain Mediterranean countries. Learn more.

Read This Acclaimed Love Story

There’s a whole lot of history, intrigue, and excitement in the 59 years Offshore Sailing School has been in existence. When Steve Colgate started writing his “vignettes,” Doris said, “We need to get these in a book!” And so they did, along with an amazing tale of how they built Offshore Sailing School into an iconic brand, and turned their lives into a tale of one adventure after another. Renowned author, Herb McCormick, captured the Colgate story in this intriguing biography that so may have said they couldn’t put down. Purchase OFFSHORE High on, in bookstores (list price $39.95), or order a special autographed copy here

800-221-4326 ♦ 239-454-1700 ♦


Our popular family ‘Tweens and Teens family vacation package is available for two adults (18 + age) learning to sail together with up to two kids*, ages 7-17. This is an amazing experience that many parents say is the best way for the family to bond and re-connect. To take advantage of this very special offer, pick a date when your kids are out of school and enroll in a 3-day/5-night Learn to Sail vacation in St. Petersburg or Captiva Island, Florida; or 3day/6-night Scrub Island Resort course in the British Virgin Islands. This family course is also available in Key West, Florida, but you will make your own accommodation arrangements.

*Third child between age 7-17 may be added to this package for $750 plus resort amenity fee, if applicable.

Learn More!

Call 888-454-7015 or 239-454-1700


OUR 60th YEAR IS IN 2024! 

Steve and Doris Colgate at the Annapolis Sailboat Show, Annapolis MD

Not too many companies surpass 60 years with their original leaders still at the helm. Living in southwest Florida, those leaders have become somewhat of a legend. The biography of Steve & Doris Colgate, and the history of Offshore Sailing School was published in October 2021. You can can order OFFSHORE High on our Book Store page, at or your local bookstore.  This revealing biography is an in-depth compendium about the Colgates’ lives, their love of sailing and each other, and the building of America’s #1 Sailing School®.

They’re still leading the way today. Case in point: Doris was featured in the October 2019 Gulfshore Life Magazine as one of five impressive “Game Changers” in Southwest Florida.

Steve Colgate started Offshore Sailing School on the back of a cocktail napkin in November 1964. Doris met Steve in January 1968 when she took a racing course he ran in the Bahamas. They are now both in the National Sailing Hall of Fame! Read more about the evolution of Offshore Sailing School in About Us, Steve’s bio here and Doris’ bio here.


Our weekly newsletter is filled with interesting stories, industry updates, and sailing course specials. Visit our Sailing Newsletter Sign-Up page. Got a story idea? Send it to Offshore Sailing’s VP, Director of Sales & Marketing, Beth Oliver: