Quick connect

Bookmark and Share

Florida Sailing School

Your Florida Sailing Vacation is waiting!

Our Florida sailing schools are the perfect place to learn new skills, brush up on techniques or take your sailing career to the next level. Warm waters and sunny skies allow Offshore Sailing School to operate year-round from three different yet uniquely stunning Gulf Coast locations.

Whether your interests run to laid-back beachside vacations or an urban cultural atmosphere with shopping and world-class museums, sailing courses Florida is a favorite vacation getaway.

Advantages of an Offshore Sailing School Vacation

  • Complete sailing education
  • Top notch instructors
  • Sailing certification
  • Best sailboats
  • 130,000 graduates
  • Only the best textbooks
  • Fine waterside destination resorts
  • More than 50 years of sailing education experience


The casual structure of a sailing vacation with Offshore Sailing School lets you spend the day learning new sailing techniques or enhancing old skills. Afterwards, spend the evening relaxing and unwinding at a luxury resort right on the beach.

Owners Steve and Doris Colgate designed their Florida sailing schools for all ages and skill levels. Couples, singles, families and even bachelor parties and girlfriend getaways can make a great sailing vacation. Non-sailors can play on beautiful white sand beaches or participate in resort activities and kid camps while sailing school students learn the ropes and lines of sailing courses.

Florida Sailing School Locations

Your Florida sailing lessons can be at: the Pink Shell Beach Resort & Marina on fun-filled Fort Myers Beach; South Seas Island Resort on beautiful Captiva Island, known as "Florida's Tahiti;" or The Hampton Inn & Suites in historical downtown St. Petersburg right on Tampa Bay.

Ft. Myers Beach, FL

Surrounded by sparkling blue bays and the Gulf Coast , the Pink Shell Beach Resort & Marina is a nature lovers dream minutes from casual downtown music and eateries. The resort is located on Florida’s southwest Gulf Coast and is home to egrets, great blue heron and dolphins. Large lanais overlook the Gulf and make a pleasing place from which to view Florida's amazing Gulf Coast sunsets. All levels of sailing courses are offered at Fort Myers Beach, including cruising and big boat catamaran sailing. Navigate the inner channel and experience open Gulf sailing as you glide through the turquoise-colored waters of the Gulf of Mexico.

Offshore Sailing School Ft. Myers Beach
Pink Shell Beach Resort & Marina
275 Estero Blvd.
Fort Myers Beach, FL 33931


Florida Sailing School - Offshore Sailing

Captiva Island, FL

The South Seas Island Resort offers the luxury of an exclusive 350 acres vacation resort right in the middle of a wildlife sanctuary. The resort is surrounded by bays, lagoons, estuaries and miles of shell-scattered white sand beaches. Manatees, dolphins, egrets, ibis and many other native birds and animals can be observed from the resort. Activities and amenities include a fine spa and exercise center, golf and tennis, fishing, running, biking and jogging. Kayaking tours and golf cart rental are available. Offshore Sailing School’s premier location, South Seas Island Resort offers educational and fun programs for children and teens. Sailing vacations include introductory courses, weekend bareboat refreshers, live aboard cruising courses at all levels, learn to sail and performance sailing courses.


Offshore Sailing School Captiva Island
South Seas Island Resort
P.O. Box 194
Captiva Island, FL 33924


St. Petersburg, FL

Next to the St. Petersburg Yacht Club, the Mediterranean-styled Hampton Inn & Suites in historic downtown St. Petersburg offers the culture, sports and recreational activities of an urban area right on the waterfront of Tampa Bay. Close to the white sands of St. Petersburg Beach, nearby attractions include the Salvador Dali Museum, Tropicana Field, the Museum of Fine Arts and Mahaffey Theatre. Hotel amenities include free high speed Wi-Fi, a fitness room and a heated pool. A deluxe free breakfast welcomes a day of sailing Tampa Bay’s many anchorages, barrier islands and wide open water. The St. Petersburg location features learn to sail, fast track to cruising and live aboard cruising courses. Cruise through Tampa Bay, past the Skyway Bridge and out into the Gulf of Mexico while making stops at scenic spots such as Egmont Key, the Manatee River, and Longboat Key.

Offshore Sailing School St. Petersburg
The Hampton Inn & Suites
80 Beach Drive, NE
St. Petersburg, FL 33701

Florida sailing courses provide daysailing, Gulf cruising and navigational skills 


Get Started Now

An Offshore Sailing School Florida sailing vacation is for anybody that loves the outdoors, enjoys being on the water and wants to learn a new skill. You’ll sail away with not just a love of the water but with sailing skills that last a lifetime.

Call us now at 888-454-7015 or Request a Quote to find out how easy it is to sign up for one of our sailing courses. Our Friendly Sailing Instructors are standing by to answer all your questions!


View Offshore Sailing School Locations in a larger map

 Sailing Lessons Back to Top button