Dockside Chats with Steve Colgate

Tune into Offshore’s YouTube Channel for fun stories with Steve – from Steve and Doris Colgate’s biography OFFSHORE High. Find out why sailing is so much fun!

Become an Offshore Sailing School Instructor!

If you are passionate about teaching sailing, we want to talk to you. See our Employment Opportunities page to learn more.

Learn to Sail

Our signature OSS 101 Learn to Sail Course is an amazing start to an exciting new lifestyle. Take the helm of a sleek Colgate 26 sailboat on a 3-day sailing lessons vacation.

Learn to Cruise
The OSS 103/104 Live Aboard Cruising Course gets you ready to see the world under sail. Learn on a beautiful big monohull or catamaran. You can also do the same course, staying ashore each night at a gorgeous resort.

Learn on Catamarans

OSS 103/104/114 Catamaran Live Aboard Cruising prepares you to skipper an impressive big sailing catamaran. 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 graduates and experienced sailors get first dibs at seeing the world under sail! Hosted flotilla cruises, organized and led by Offshore staff, are hassle free. You do the sailing, Offshore takes care of all the details.

Learn to Race and Win Races

OSS 102 Performance Sailing is all about sail-fast techniques. Then take OSS 109 Performance Race Week, our Signature Racing Program, and learn to win from expert sail-race coaches and renowned racing experts.

Learn to Power Like a Pro

OSS 112 Fast Track to Power Cruising gives you the skills to captain a power cat 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 Coast 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 and productive escape with a fun-filled 4-hour or full-day Team Building adventure on our fleet of easy-to-handle Colgate 26 sailboats. Consider a leadership event or a pleasant group outing under sail.

Captiva Island, Florida

Sail where dolphins and manatees play. Come to South Seas Island Resort, a 330-acre island destination surrounded by sandy beaches, bays and the Gulf of Mexico.

Cape Coral Marina Village, Florida

Learn to Sail or get your Catamaran Bareboat Cruising Certification at The Westin Cape Coral Resort at Marina Village near Sanibel Island in Southwest Florida.

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.

Fort Myers Beach, Florida

Choose The Pink Shell Beach Resort & Marina where every room has amazing views of spectacular Gulf sunsets and sugar-white beaches stretch for miles.

Tortola, British Virgin Islands

Earn Bareboat Cruising Certification on a Moorings sail or power charter yacht. 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 with terrific museums, restaurants and night life.