Florida Sailing School | Sailing Lesson Vacations in Florida


Sailing Lessons in Florida on the Gulf of Mexico

Offshore Sailing’s Florida sailing school is ideal for learning new sailing skills to begin your sailing lifestyle. Our Florida sailing vacations take place in warm Gulf of Mexico waters under sunny skies, providing the perfect destination for year-round sailing lessons at four different yet uniquely stunning locations. Whether you like laid-back beach resorts or an chic, urban cultural environment at water’s edge, our Florida sailing schools in St. Petersburg, on Fort Myers Beach, Cape Coral, and Captiva Island are all great locations for learn to sail vacations. Learn more about our course offerings below.

Great Team Building and Leadership Development Sailing Programs

Hold your next meeting in the Greatest Classroom in the World!® Take a tour of Southwest Florida’s meeting spaces and amenities and add a unique team building event with our Corporate Sail-Race Challenge® sailing events available at the Pink Shell Beach Resort & Marina on Fort Myers Beach, and at South Seas Island Resort on Captiva Island, or The Westin Cape Coral Resort in Cape Coral, Florida. 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.

Sailing Lesson Vacations in Florida

Four Florida sailing school locations beckon you – “Florida’s Tahiti” at South Seas Island Resort on captivating Captiva Island, fun-filled Pink Shell Beach Resort & Marina on Fort Myers Beach, action-packed The Westin Cape Coral at Marina Village and Tarpon Point Marina, or The Hampton Inn & Suites in trendy downtown St. Petersburg on Tampa Bay. Sign up for a sailing vacation in Florida today! Take a look at this video, and sign up for sailing lessons in Florida today!

Florida Sailing Lessons and Sailing Adventures