Learn to Cruise And See the World


Great Vacations Start with the Perfect Course


Go from Couch to Captains Chair in One Week


Give Your Team the Competitive Edge


Make New Friends when you Learn to Sail


Learn to Cruise and see the World under Sail


Make Winning Races your Next Best Getaway

Sailing and Boating Adventures Change Lives!

Learn to sail, handle big cruising boats, or head over the horizon on a passage making course at one of our Florida or British Virgin Islands getaways. Embrace the sailing and boating lifestyle and open a whole new world of fun adventures on the water!  Take sailing or boating lessons in Southwest Florida on Captiva Island, Key West, or in St. Petersburg, or head to the gorgeous British Virgin Islands. Then join one of our amazing hosted sailing vacations in the Caribbean and exotic locales and see the world under sail!

Call us today at 800-221-4326 or 239-454-1700; email Info@OffshoreSailing.com to learn more.

Happy Sailing! Have Fun Boating!
Steve & Doris Colgate
and the entire Offshore Sailing School Team

“Fast Track® Sail and Power Lessons are Amazing,” Say Offshore Graduates!

At Steve and Doris Colgate’s Offshore Sailing School, in-depth sailing lessons and courses on power cruise yachts give you the skills to see the world on your own yacht or on charter vacations in idyllic island retreats. Our two most popular courses are OSS101 (learning to sail) and OSS 101/103/104 (novice to navigator) in one week! If you are new to Offshore Sailing School, we welcome you to a whole new lifestyle.  If you are already an Offshore Sailing School graduate, welcome back! And thank you for being one of our more than 160,000 graduates! America’s #1 Sailing School® is entering our 60th year!  Join us and our graduates in celebrating this amazing milestone!

The Greatest Classroom in the World!®



Fast Track to Cruising®- OSS 101/103/104

Our most popular learning adventure takes you from Couch to the Captain’s Chair in just eight days. You earn three US Sailing certifications — Basic Keelboat, Basic Cruising and Bareboat Cruising — starting with two days on a 26 footer, then six on a gorgeous big cruising monohull or catamaran yacht. At course end you’re ready to pursue the cruising lifestyle with confidence and ease!


I’ve had sailing courses from other organizations but this is the best set of courses I ever experienced.

Jesse JohnsonAustin, Texas

"Colgate’s Offshore Sailing School is truly the best sailing school. Everything is first class, and well worth the money and time spent."

Tom BisanzFrisco, Texas

"Fast Track to Cruising gave us the knowledge and skills to enjoy cruising for the rest of our lives."

Karen and Kevin MarcilliatMableton, Georgia

"Amazing course! I’ve done a lot of sailing, and learned a lot during week. My wife went from novice to knowledgeable and reliable."

Robert and Betsy LahueWyckoff, New Jersey

"This was our third course with Offshore. The instructors really set Offshore apart from other sailing organizations."

Andrew and Erin DeakRocky River, Ohio

"Offshore made it easy to learn! One of the best weeks ever. My dad and I couldn’t have had a more productive and enjoyable adventure."

Mark WaltzMuskego, Wisconsin

"I took the Fast Track to Cruising Course and went from non-sailor to confident cruiser in one week!"

Gabriel EmanuelliMiramar, Florida

"What a fantastic experience! Our Fast Track week was fun and educational from beginning to end."

Todd and Lois GillenwaterCharleston, West Virginia

"The instructors were amazing. I learned a lot, had fun, and can’t stop telling everyone how cool this experience was."

Charles ZahalkaLas Vegas, Nevada

"We are amazed at how much we learned in such a short period of time. We left feeling confident and eager to step aboard again."

Danielle SteinbergGeorgetown, Kentucky


If you are looking for a new opportunity, to work in a field you love, we have several key positions available that are all about sailing! Learn more . . .

New Total Immersion Fast Track Sailing Course

Offshore’s new Fast Track course covers Basic Keelboat, Navigation and Small Boat Cruising in 6 packed days of experiential learning. Learn more . . .

Sailing Magazine Features Offshore Sailing School

Instead of lazing around a pool, sailors are packing their seabags and heading for learn-to-sail vacations in tropical locations, says Sailing Magazine in their February 2020 issue. Learn more . . .

Canadian Yachting Magazine Publishes "Dear Doris" Story

An avid sailor falls in love with a NON-sailor and writes Doris Colgate for advice on how to turn him on to sailing. Learn more . . .

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