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

We're Back on Captiva!

Now you have four super locations where you can learn to sail, cruise, and race. Return with Offshore to the gorgeous beaches of  SW Florida at the fun-filled Tween Waters Island Resort & Spa on Captiva Island! Or join us at our other great locations in St. Petersburg, FL  Scrub Island Resort and The Moorings in the gorgeous British Virgin Islands.

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, Amazing On-Water Adventures!

At Steve and Doris Colgate’s Offshore Sailing School, in-depth sail and power programs give you the skills to see the world on your own yacht or on charter vacations 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 entering our 60th year!  Jon us!

The Greatest Classroom in the World!®


Request the Offshore Sailing School® Brochure

Follow the link below to request the Offshore Sailing Brochure and start planning your next adventure today!

Request Brochure


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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