Learn to Sail And Take The Family Cruising



Learn to Cruise & See the World


Learn To Cruise And Charter Catamaran Sailboats



Go From Couch To Captains Chair In One Week


Choose Sailing For Teambuilding & Leadership Skills


Make New Friends On A Fast Track To Cruising Adventure


Learn to Cruise And See The World Under Sail


Make Winning Races Your Next Best Getaway


Sailing & Boating Adventures That Change Lives!

Learn to sail, learn how to confidently handle a live-aboard yacht, 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 with an Offshore Sailing School Fast Track® experience and open a whole new world of fun adventures on the water!  Take sailing lessons or boating lessons, then join one of our amazing hosted sailing vacations in the Caribbean and exotic locales, and see the world under sail!

At Steve and Doris Colgate’s Offshore Sailing School, in-depth sailing lessons and powerboat courses give you the skills to captain your own yacht or skipper a chartered yacht in idyllic island retreats. 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 celebrating 60 years!  Join us in applauding the amazing Offshore Sailing School team, dedicated to providing The Greatest Classroom in the World®!

Call us today at 888-454-7015 or 239-454-1700; or 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!

Close-up of a man sitting side-by-side on bench of cockpit, with his wife who is steering a large catamaran

At Steve and Doris Colgate’s Offshore Sailing School, in-depth sailing lessons, power cruise lessons and sailboat cruising lessons on big catamarans and monohull cruising boats 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 Learn to Sail OSS 101 and Learn to Cruise OSS 101/103/104. Combine both courses in our rewarding Fast Track to Cruising® eco-friendly learning vacation, and go from novice to navigator in one week! If you are new to Offshore Sailing School, we welcome you to a whole new sailing and boating 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! Offshore Sailing School is America’s #1 Sailing School®, celebrating our 60th anniversary in 2024!  Find out why sailing is so much fun. Join our team and our graduates in applauding this amazing milestone!

If you enroll in a 3-day or longer sailing course at Offshore Sailing School between January 1 and September 30, 2024 you will automatically be entered into a raffle to win a charter with The Moorings in the British Virgin Islands. So what are you waiting for? Contact our Sales Team today!

The Greatest Classroom in the World!®



Couple Sailing

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!

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.

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.



Call Us Today

888-454-7015     or    239-454-1700

Ask our experts about training, group packages, vacations, and more!