Dockside Chats with Steve Colgate

Tune in to Offshore’s YouTube Channel chats with Steve Colgate, whose life-long passion for sailing is vividly described in Steve and Doris Colgate’s biography OFFSHORE High. Steve’s love for sailing is truly addictive!

Join Our Faculty and Teach Sailing!

If you are passionate about teaching sailing and have the right credentials, we would love to talk to you.  See our Employment Opportunities page to learn more. Book an appointment with a our dedicated Operations Team.

Learn to Sail

OSS 101 Learn to Sail is an amazing start to an exciting new lifestyle.  Three full days of classroom and on-water sailing lessons on sleek Colgate 26 sailboats, give you the confidence to handle a sailboat up to 30′!

Learn to Cruise on 40′-50′ Monohulls

OSS 103/104 Live Aboard Cruising Course is the next step up from OSS 101 Learn to Sail. Gain the skills to skipper your own yacht or on a bareboat charter in phase 2 of Offshore’s popular Fast Track® to Cruising course.

Learn to Cruise on 40′-45′ Catamarans

OSS 103/104/114 Catamaran Live Aboard Cruising prepares you to sail and skipper big twin-hulled yachts. New to sailing? Enroll in a Fast Track to Cruising Course and get ready to charter or purchase your own private yacht.

Flotilla Cruise Vacations

Offshore Sailing School graduates and experienced sailors love our hosted Colgate Sailing Adventures® flotilla cruises. Organized and led by Offshore staff, you enjoy week-long vacations in exotic lands, with like minded sailors who love seeing the world under sail!

Become a Competitive Sailor

OSS 102 Performance Sailing is all about sail-fast techniques. The original Performance Race Week® OSS 109, is the industry’s signature racing program taught by renowned racing experts.

Learn to Skipper Power Yachts

OSS 112 Fast Track to Power Cruising gives you the skills to captain a big power boat on charters with family and friends. Gain ultimate confidence while living and learning on a beautiful power cat in the British Virgin Islands.

Learn Passage Making

OSS 106 Coastal Passage Making and OSS 108 Offshore Passage Making are the ultimate blue water sailing school experiences. Discover how to safely sail round-the-clock. Achieve skills and confidence to fulfill your cruising dreams!

Team Building for Your Group

Give your team a rewarding escape with an action-packed half- or full-day Team Building adventure, or a pleasant group outing they’ll long remember – all on our fleet of exciting, easy-to-handle Colgate 26 sailboats.

Captiva Island, Florida

Sail where dolphins and manatees play. Come to ‘Tween Waters Island Resort & Spa on Captiva Island, where shelling is amazing on vast sandy beaches, and  sailing on warm waters surrounded by wildlife is so much fun.

Scrub Island, British Virgin Islands

Learn to Sail or earn your Bareboat Cruising Certification at the gorgeous Marriott Autograph Scrub Island Resort, Marina & Spa in the British Virgin Islands. Do both courses in one week and start your sailing lifestyle!

Tortola, British Virgin Islands

Earn Bareboat Cruising Certification on a 40′-50′ Moorings sail or power charter yacht. Start in the busy Moorings charter base on Tortola.  Learn as you sail from island to island, stopping each night in a different port in paradise.

St. Petersburg, Florida

Your vacation learning to sail on Tampa Bay starts from the waterfront Hampton Inn & Suites, in trendy downtown St. Pete, surrounded by terrific museums, restaurants and night life.