Summer Sail 2022  –  SAVE 10%!

Sail or cruise into summer with 10% savings on all 3+day US Sailing and Powerboating certification courses on Florida’s Gulf Coast or the beautiful British Virgin Islands! Book by April 15, 2022, for valid courses starting June 4, 2022, and ending by September 3, 2022. Valid courses:

*Requires minimum of two students enrolled to run course.

Summer Sail savings may not be combined with family ‘Tweens & Teens sailing vacation package, Offshore Sailing School graduate discount, nor Military discount, which already provide great value!

How About a Brand New Colgate 26 for Family Fun Adventures in 2022 . . .

This is a rare opportunity at great savings – your own fast and fun Colgate 26 – ready to sail this Spring! Order before  April 15, 2022, with just a 20% deposit and enjoy a one-time holiday discounted price of just $79,750, including sails and outboard motor! Other boats in this size range charge extra for sails and motors. Your Colgate 26 holiday special is just that – truly very “special.” For more information, visit and contact Steve Colgate to get your order in.  We guarantee you’ll have a ton of family fun!

Or a Fabulous Experiential Vacation that Keeps on Giving!

Purchase a sail or power course vacation and enjoy a lifetime of sailing and boating adventures. For those with no or little sailing experience, our  3-day Learn to Sail course starts at just $1,845 per person. Want to join the cruising lifestyle? Combine three certifications in our 8-day Fast Track® to Cruising course starting at $5,325 per person. Choose one of our delightful Florida locations, or the glorious British Virgin Islands, but act now! Sailing and boating is at an all-time high because on-water fun is what everyone wants to do. How about you?

Read This Acclaimed Love Story

There’s a whole lot of history, intrigue, and excitement in the 58 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 ♦


One of our most special activities is our ‘Tweens and Teens Learn Free family vacation program, where up to three kids, ages 7-17, learn to sail with two adults for free. That’s a savings of nearly 60%! This is an absolutely amazing experience, one that many parents say is the best way for the family to bond and stay connected. To take advantage of this very special offer, pick a date when your kids are out of school and sign up for a 3-day/5-night Learn to Sail vacation at South Seas Island Resort on Captiva Island or Pink Shell Beach Resort on Ft. Myers Beach, Florida. You arrive on Sunday and sail full-days Monday through Wednesday, and have two extra days to enjoy resort amenities and the surrounding area. You check out Friday unless you book extra nights. Both of these family-friendly resorts offer lots of things to do when you are not out on the water.

Learn More!

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


When all of our sailing school locations closed down between April and May, 2021, due to the pandemic, Steve and Doris Colgate thought sailors and would-be sailors might want a little home-made entertainment. So, they put together a series of short, inspirational video vignettes with Steve talking about his fascinating sailing career. Doris shares some stories too!

70 #DocksideChatswithSteve have been produced and posted on Offshore Sailing School’s Facebook page. You will also find these stories on the Offshore Sailing School YouTube Channel . Our channel features these Chats, plus sailing tips, tours of our resort locations, recaps of our flotilla vacations and other special events. These stories are featured in OFFSHORE High, the new biography published in Fall 2021 about Steve and Doris, and Offshore Sailing School.


My experience with Offshore Sailing School was life changing. I enrolled in the Fast Track to Cruising® course with my husband Matt to see if live aboard sailing and bareboat chartering was for me. I graduated with a lifetime certification not only with sailing knowledge but with a new love for learning. The course surpassed all my expectations and my husband and I now have a new hobby to share!

Ellen Orenstein – Atlanta, GA
Fast Track to Cruising – Captiva Island, FL  June 2019



888-454-7015 or 239-454-1700



Suffolk University MBA Candidates


Sailing is the by far the best way to bring teams together and develop leaders who will deftly guide those teams. Offshore Sailing School can accommodate teams of 8 and up aboard two Colgate 26 sailboats or more in our unique Corporate Sail-Race Challenge® sailing lessons. In addition to the Pink Shell Beach Resort on Ft. Myers Beach, Offshore Sailing School hosts team building and group sailing excursions at South Seas Island Resort on Captiva Island, and The Westin Cape Coral Resort in Cape Coral, Florida. Groups of up to 10 may also be accommodated at Scrub Island Resort in the British Virgin Islands. Contact Beth Oliver today to learn how your team can perform at the highest level:, 239-985-7516.

Start Learning Now!

888-454-7015 or 239-454-1700


We have a full spectrum of sailing vacations available through our Colgate Sailing Adventures® Flotilla Cruises – for Offshore Sailing School grads and sailors who love to sail. The group in this photo are at the Meet and Greet dinner for the last Tahiti flotilla cruise. These sailing vacations are the most delightful way to explore the world under sail. We charter the yachts, research and provide the itinerary, put the crews together based on friendships and sailing experience, and best of all – we provide expert trip leaders who love to sail and want you to have the time of your life! View our next amazing destinations here. Check out this video from our 2019 Colgate Sailing Adventures® flotilla sailing vacation aboard six Moorings cruising yachts in the British Virgin Islands.

Book a Cruise!

888-454-7015 or 239-454-1700


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

Not too many companies surpass 50 years with their original leaders still at the helm. Living in southwest Florida, those leaders have become somewhat of a legend. And now a Biography will debut at the October 2021 boat show in Annapolis, the second weekend in October. If you can’t wait, you can pre-order on our Book Store page, at or your local bookstore now.  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.

And every day the Colgates wake up with a smile, do their morning walk, then head to the office to work closely with a dedicated team that works tirelessly to introduce more people to the sailing lifestyle. And at the end of very busy days, the Colgates often say, “Where did the years go?”

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. Read more about the evolution of Offshore Sailing School in our About Us section on this website: 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 at