Learn to Sail: Embrace the Sailing Lifestyle
From the city skylines of Florida’s Tampa Bay and delightful waters of Pine Island Sound and Gulf of Mexico, to the tropical trade winds of the verdant British Virgin Islands, Offshore Sailing School provides a variety of rewarding Learn to Sail vacation opportunities. 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 “Buy–the-Boat” family course. Sailing instruction packages include tuition and accommodations which vary by season.
As an Offshore Sailing School graduate, you receive many alumni benefits including your first year of US Sailing membership free, $300 graduate discounts on future courses, up to 15% discount on charters with The Moorings, and exciting Colgate Sailing Adventures® hosted flotilla vacations. View Graduate Benefits here.
Learn to Sail and Earn US Sailing Basic Keelboat Certification
The comprehensive OSS 101 Three-day Learn to Sail Course takes you through the intermediate level, ready to confidently skipper a sailboat up 30′ without a captain aboard. Buy a package including accommodations at one of our resort locations, or commute from home if you live in the area. Learn more about about the 3-day Learn to Sail OSS 101 course here. Click on your location choice below to see where you can learn OSS 101 sailing skills.
- Scrub Island Resort & Spa, British Virgin Islands
- Pink Shell Beach Resort & Marina, Ft. Myers Beach, Florida
- Tween Waters Island Resort & Spa, Captiva Island, Florida
- Downtown Hampton Inn & Suites, St. Petersburg, Florida
- Beachside Resort & Residences/Stock Island Yacht Club & Marina, Key West
Get on the Fast Track to Cruising®
OSS 101/103/104 Fast Track to Cruising® is our most popular program. In 8 rewarding days, you go from couch to the captain’s chair, gaining the confidence to helm your own 40′-50′ yacht or while charter cruising in exotic cruising ports. 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
Value-priced Family Fast Track® to Cruising Package 
Our popular Fast Track to Cruising® Course is available at all locations, except Tortola, BVI. In this sail and learn adventure, a family of 4* (two adults and two family kids, minimum age 12, maximum age 25) enjoy the full course at a special Family Cruising package price. Learn the basics on a Colgate 26, then board a 44′ monohull or 40′ catamaran yacht and learn while living aboard for the next 6 days. This special offer is a delightful opportunity to reunite family members, learn the skills to bareboat charter on countless future boating vacations! Call 888-454-7015 for availability and monohull or catamaran pricing.
*Fifth family child between age 12 and 25 may be added for additional fee. Two-bedroom suite may be available with four queen beds and sleep sofa at additional expense; ask for availability at time of enrollment.
Take a Sailing Lesson
Just want to find out what sailing is all about? A two-hour or longer sailing lessons is a great way to “test the waters” and learn how much fun sailing truly is. Available at most Offshore Sailing School locations, cost is $125 per person per hour ($250 minimum for two-hour lesson). To learn more, please download 2024 Sailing Lessons.
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.
