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Learn to Sail: Embrace the Sailing Lifestyle

From the city skylines of 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 in fantastic destinations. A learn to sail holiday in Florida and the British Virgin Islands requires no prior experience. All beginner sailing courses are taught by professional sailing instructors, with no more than four sailing students on each boat, unless you ask for a private family course. Sailing instruction packages include tuition and accommodations which vary by season. We also have sailing lessons just for women only that take you from beginner to confident cruising sailor!

As an Offshore Sailing School graduate, you will receive many alumni benefits, such as your first year of US Sailing membership free; $300 graduate discounts on future courses and Colgate Sailing Adventures hosted flotilla vacations, and more. View Graduate Benefits here.


OSS 101 – Learn to Sail and Earn US Sailing Basic Keelboat Certification

These comprehensive 2 or 3-day courses take you through the intermediate level on vacation or commuting from home. You can learn more here. Click on your location choice below to view resort amenities now! Call 888-454-7015 to check on status of resort locations as some marinas are under repair from Hurricane Ian in Southwest Florida, September 2022.

OSS 101/103/104 – 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 or sailing your own sailboat. You earn three US Sailing Certifications and go home with skills and knowledge to take the helm of cruising boats up to 50′.

“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

Read more testimonials here

Take a Sailing Lesson

Not yet ready for the complete sailing course? At some of our locations you can take an introductory beginner 3-hour sailing lesson, and discover why sailors have so much fun. Advanced reservation required. Not available at all locations.

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. Great prep for the on-water sailing sessions.