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. Sailing instruction packages including tuition and accommodations vary by season. Some tuition-only courses and learn to sail vacation packages may be booked online. We also have women-only courses that take you from beginner to confident cruising sailor!
Start Learning Now!
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
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. Lessons are available at most Offshore Sailing School locations.
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. This introductory course is available at our Captiva Island and Ft. Myers Beach locations in Florida.
Learn to Sail and Earn US Sailing Basic Keelboat Certification
These comprehensive 3-day or 5-day courses take you through the intermediate level on vacation or commuting from home. Ready to book your course? You can learn more here or just click on your location choice below and book your full course package (including accommodations at resort locations) now!
Five-Day and Three-Day Learn to Sail Certification Courses
- Scrub Island Resort & Spa, British Virgin Islands
- South Seas Island Resort, Captiva Island, Florida
- Pink Shell Beach Resort, Fort Myers Beach, Florida
- Hampton Inn & Suites, St. Petersburg, Florida
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. You earn three US Sailing Certifications and go home with skills and knowledge to take the helm of cruising boats up to 54′.