Learn to Sail: Embrace the Sailing Lifestyle

From the city skylines of the Hudson River and Tampa Bay to the emerald waters of the Gulf of Mexico, and the tropical trade winds of the verdant British Virgin Islands, Offshore Sailing School provides a variety of learn to sail vacations for new and returning sailors on some of the most scenic and exciting waterways in the world for sailing instruction.

Learning to Sail on Vacations and Getaways

Learn to sail at one of our resort destinations, on a learn to sail vacation in Florida and the British Virgin Islands where dolphins and manatees play in your wake, or “get away without going away” in the exciting waters surrounding New York City. Sailing instruction packages including tuition and accommodations vary by season. Some tuition-only courses and learn to sail vacation packages may be booked online.
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Beginner to Intermediate Learn to Sail Courses

We have several sailing for beginners options at all of our locations. Our Learn to Sail courses require no prior experience. All are taught by the best sailing instructors you’ll find. Unless you ask for a private family course, our instructors never teach more than four students on each boat.

“Anyone who is looking for a top-notch, unforgettable, hands-on experience should take an Offshore Sailing School course! Our instructors were Amazing!! They were incredibly patient, encouraging, knowledgeable, positive, helpful, professional and CALM! We were impressed with the variety of teaching techniques used to make learning fun and interesting for us both. The course exceeded our expectations in every way.”


S&S Rutherford – Thamesford, Ontario

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Take a Sailing Lesson

This is the perfect introduction to sailing for beginners. Get out on the water with a 2-hour sailing lesson, and discover why sailors have so much fun.

Try an Intro to Sailing Course

This 6-hour sailing instruction is a great way to “test the waters” if you’re not yet ready for a full sailing certification course.

Learn to Sail and Earn Certification

These comprehensive 2-day, 3-day or 5-day courses take you through the intermediate level on vacation or commuting from home.

Get on the Fast Track to Cruising®

Our most popular program takes you from couch to the captain’s chair in seven days, with confidence to start charter cruising.

Learn to Sail Online

This information-packed Online Learn to Sail Course mirrors classroom sessions in our 3-day Learn to Sail Certification course with videos, diagrams, interactive exercises, and tests.

Start Sailing Today!

Call 888-454-7015 or 239-454-1700

Email Sail@OffshoreSailing.com