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Florida Sailing School


Captiva Island, Fort Myers Beach, and St. Petersburg, Florida Sailing Lessons on the Gulf of Mexico and Tampa Bay

‘Tween Waters Island Spa & Resort, Captiva – Florida Sailing School

Pink Shell Beach Resort & Marina – Florida Sailing School

Offshore Sailing currently teaches all levels of US Sailing certification courses on Captiva Island, Fort Myers Beach, and St. Petersburg, Florida.

Captiva Island and adjacent Sanibel Island on Florida’s Gulf Coast are known as the shelling capital of the world, with pristine shoreline, miles of sugar-sand beaches, acres of protected habitats, and wildlife on land, in the sea, and sky. There is something for everyone on captivating Captiva! We’re based at ‘Tween Waters Island Resort & Spa, situated between Pine Island Sound and the Gulf of Mexico, with a private beach, complimentary bicycle use, a spa, multiple pools, fishing dock and watersports, multiple dining options, all on property. Cruise to waterside tiki huts, restaurants, and boutiques. Escape into private anchorages and explore natural habitats on barrier islands.

The Fort Myers Beach Florida Offshore Sailing School on Florida’s Gulf Coast is just 30 minutes from Southwest International Airport where flights from all over the country and abroad land sailing adventurers. Sitting on miles of white sandy beach overlooking the Gulf of Mexico, the Fort Myers Beach Offshore Sailing School location is perfect for learning to sail on Colgate 26 keelboats, and Fast Track to Cruising courses on 40′-47′ sailing catamarans and big monohull sailing yachts. The marina is just minutes from Gulf of Mexico open water sailing. When you return from a day of sailing lessons or big sailboat cruising instruction that get’s you ready for charter vacations, you’ll find great activities like kayaking and paddle boarding to enjoy, followed by a delectable island meal overlooking the beach.

Stock Island YC & Marina, Key West, Florida Sailing School

Offshore Sailing School in Key West Florida. This well-protected marina along the unspoiled Atlantic Ocean shoreline is the perfect location for sailing lessons on Offshore Sailing School’s Colgate 26 keelboats, and Fast Track to Cruising courses on a new Lagoon 40 catamaran.  In minutes you are sailing out the Boca Chica Channel, with gorgeous maritime views. The marina has a large swimming pool if you want to take a dip after your lessons and before you head back to your hotel. There’s also a Ship Store where you can pick up some snacks and ice cream.

Downtown St. Petersburg, Florida

The Hampton Inn & Suites, St. Petersburg, Florida Sailing School

St. Petersburg  is ideal for learning new sailing skills and gaining bareboat cruising certification. We’re based at the Downtown Hampton Inn & Suites and our boats are across the street in the Municipal Marina. This convenient hotel is in the middle of this vibrant town known as a haven for sailors who love the sea and living the sailing lifestyle. Florida sailing vacations get you out on the warm waters of Tampa Bay and the Gulf of Mexico, where you can enjoy year-round sailing lessons. Whether you like laid-back beach resorts or an chic, urban cultural environment at water’s edge, our Florida sailing school in St. Petersburg, is a great location for learn to sail and sailboat cruising vacations.  Learn more about our course offerings below.

Team Building and Leadership Development  Programs

This sailing program is available in St. Petersburg, Florida, for groups of 8-16 participants. Hold your next meeting in the Greatest Classroom in the World!®  Watch video.

Set Sail in Exotic Ports Around the World!

Cruise with Offshore Sailing School on our fabulous Colgate Sailing Adventures® cruises all over the world! View our highlights video from our Caribbean sailing flotilla in the British Virgin Islands here.

Florida Sailing Lessons and Sailing Adventures

In addition to sailing courses for beginners, with Offshore Sailing School you can enjoy great sailing and cruising courses on 40′-51′ sailing yachts. Take a look at this video, and sign up for sailing lessons in Florida today!

Learn to Sail 

Fast Track to Cruising® 

Bareboat Charter Courses

Live Aboard Cruising 

Weekend Warrior Monohull or Catamaran Docking Refresher

Weekend Warrior Monohull Catamaran Endorsement 114

IPC Prep with Bareboat Cruising Certification & Cat Endorsement

Catamaran Live Aboard Cruising 

Call 888-454-7015 or 239-454-1700