Learn to Sail and Embrace the Sailing Lifestyle
From Southwest Florida’s Tampa Bay and barrier islands on the Gulf of Mexico to the tropical trade winds of the Caribbean, Offshore Sailing School provides a variety of rewarding Learn to Sail and Learn to Cruise 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 vary by season and include tuition and accommodations ashore or aboard the vessel you learn on.
Offshore Sailing School graduate benefits include US Sailing membership, discounts on future courses, up to 15% discount on charters with The Moorings, and exciting Colgate Sailing Adventures® hosted flotilla vacations.
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 and crew on sailboats 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. For a very special women-only sailing vacation getaway, check out our Women’s Sail Sip Spa Learn to Sail Week and click on your location choice below to see where couples, friends, families and singles can learn OSS 101 sailing skills in the perfect vacation setting.
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′ catamaran sailboat or monohull yacht or while charter cruising in exotic cruising ports. You earn three US Sailing Certifications plus your Catamaran Endorsement 114 if learning on a sail-cat, and graduate with skills and knowledge to take the helm and go sailing on live-aboard cruising boats.
“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. 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. First you learn sailing basics on a Colgate 26, then board a 44′-48′ monohull or 40′-45′ catamaran yacht and learn how to skipper and crew a big cruising yacht while living aboard for the next 6 days. This special offer is a delightful opportunity to reunite family members and learn the skills to bareboat charter or go sailing and cruising on your own boat on countless future boating vacations! Call 888-454-7015 or 239-454-1700 for availability and monohull or catamaran pricing.
*Fifth family child between age 12 and 25 may be added for additional fee. For nights you spend at the hotel while learning to sail, ask about availability and upgrade costs for two-bedroom suites if preferred.
Take a Sailing Lesson
Just want to find out what sailing is all about? Two-hour or longer sailing lessons are 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 this PDF describing in more detail what you learn in short sailing lessons.
Learn to Sail Online
This valuable Online Learn to Sail Course mirrors classroom sessions in our 3-day Learn to Sail Certification course with videos, diagrams, interactive exercises, and tests. It is required if you do not have Basic Keelboat Certification 101 and wish to “test-out” of the OSS 101 course in preparation for taking the 103/104 cruising course. It is also a great way to renew your sailing knowledge if you haven’t sailed in awhile.
