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Sailing School on Sanibel-Captiva Island, Florida

Captiva Island Sailing at South Seas Island Resort 

South Seas Island Resort, one of the top sailing destination resorts, has been home to Offshore Sailing School on Captiva Island since 1975. Here you learn in an eco-friendly environment, absorbing the wonders of sea life, surrounded by pristine nature. Affectionately called “Florida’s Tahiti,” this Florida retreat is the perfect vacation getaway for singles, families and couples – with miles of sandy beaches, Gulf of Mexico sailing, manatees surfacing in the harbor, dolphins playing in your wake, and spectacular sunsets over the Gulf’s endless horizon. Florida sailing courses include beginner sailing lessons, cruising and bareboat charter lessons, and performance sailing courses. In 2021, Southern Living magazine chose Sanibel-Captiva Islands as the best beach towns of 2021. Call us at 888-454-7015 to receive a quote for a fun learning vacation package today.

I wanted to let you know how much I enjoyed my sailing 3.2A_CaptivaIsland_Testimonial_Judy_Cox_465x700instruction and lessons in the Learn to Sail course on Captiva Island. My instructor was terrific with a great deal of patience and a good sense of humor to boot.” 

Judy Cox – New York, NY

Read more testimonials here


Learn to Sail on Beautiful Captiva Island

Choose the five-day Learn to Sail schedule and sail in the pristine waters of Pine Island Sound in half-day sailing lessons. This invigorating Captiva Island, Florida sailing course adventure gives you a new skill with time to explore all that Captiva and Sanibel Island have to offer. If you have limited time you can take the Learn to Sail Course in two action-packed days, sailing morning and afternoon each day on Saturday and Sunday. In our new beginner to advanced Fast Track® to Sailing Course you learn to sail, gain advanced sailing skills, and learn sailboat navigation too. If your ultimate goal is to charter or purchase big sailboats, our Fast Track to Cruising® Course is your ticket to a world of sailing adventures.

Shell-Strewn Beaches and Amazing Sunsets

Around this sailing resort are many shops and a fun selection of island eateries, all within walking distance. With the Gulf of Mexico to the west and Pine Island Sound to the east, you have a clear view of morning sunrises and spectacular evening sunsets. Bring your friends and family along on vacation. Discover why South Seas Island Resort is one of Conde Nast Traveler magazine’s “Top 10 Resorts in the World for Families,” and Parents Magazine’s “Top 10 Beach Resorts.”

More About South Seas Island Resort

Accommodations include hotel suites, one to three bedroom villas, beach homes and condominiums. If you want to explore and shop off the island you may want to rent a car. To get around the resort and into Captiva Village, golf carts and bicycles rentals are available, and a free trolley travels from one end of the Captiva Island resort to the other. Off-season you can enjoy a free night on resort stays of at least four days. If you are signing up for a two-day course, add another day to explore the Ding Darling National Refuge, Bailey-Matthew Shell Museum, and Clinic for the Rehabilitation for Wildlife (C.R.O.W.) on Sanibel Island.

  • Variety of accommodations in hotel rooms, suites, villas, and homes with marina, resort, or Gulf of Mexico views
  • Kitchens or kitchenettes in all but hotel room suites
  • Refrigerator and coffee maker in hotel room suites
  • Harbourside Grill in yacht harbor and several other eateries throughout resort
  • Doc Ford’s Rum Bar & Grille at south end or resort
  • Short walk to Captiva center with many fun dining and shopping experiences
  • Complimentary trolley service throughout resort and free trolley from resort to Captiva Village
  • Par-3 executive golf course
  • State-of-the-art tennis courts at the Blackwood Tennis Academy onsite
  • Miles of running and cycling paths
  • Bicycle and golf-cart rentals
  • Kayak and paddle boarding rentals
  • Resort Pool Complex featuring private cabanas and the Crooked Snook Tiki Bar with live music on weekends
  • 15 other swimming pools located throughout the resort
  • Broad white sand beaches and great shelling
  • Spa and fitness facilities, including a yoga studio
  • Nature center
  • The Sanibel Sea School
  • Family Interactive Center
  • Parasail rides and Waverunners
  • Boat rentals
  • Fishing off the resort dock
  • Fishing excursions

While other schools teach up to 6 people on a boat, Offshore Sailing School never teaches more than four per boat and instructor unless you opt for a ‘Tweens & Teens Learn Free or Buy the Boat private sailing lessons. Rates vary by season. Please see the “What’s Included” tab for more information. Book online now or contact us for more information: 888-454-7015 or 239-454-1700; email

South Seas Island Resort has a wide variety of accommodations, ranging from hotel rooms overlooking the marina to villas accommodating up to eight on the beach, golf course and tennis courts. Please call 888-454-7015 or email to get a quote for the course and accommodations you desire during your preferred travel time period. Here is an overview of what’s included when you take an Offshore Sailing School course at South Seas Island Resort. Please check the individual courses for more details.

An overview of what’s included:

  • Your course tuition
  • Accommodations ashore and taxes on accommodations for all shore stays
  • Per person per night resort fee and tax for shore-based courses
  • Your cabin aboard for Live Aboard Cruising Courses
  • All breakfasts, lunches, snacks and three dinners aboard during live aboard courses (two dinners are on you)
  • Your course textbook(s)
  • Diploma and logbook
  • Course certification when you pass the test
  • Other items specific to each course
  • Exclusive one-year subscription to Cruising World or Sailing World magazine

Learn More

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


How to Get to South Seas Island ResortCaptiva Island, FL Map

South Seas Island Resort is on the north end of Captiva Island, connected by a short
bridge to Sanibel Island – about 1-1/2 hours’ drive from Southwest International Airport (RSW) in Ft. Myers and 3 hours from Tampa, Ft. Lauderdale and Miami airports. Taxi service is available at the RSW airport. Rental cars are available at all airports and on the resort. If you prefer to drive, you can visit a host of scenic sites as you make your way down the Gulf Coast of Florida.

Address Information:

South Seas Island Resort
5400 Plantation Road
Captiva Island, FL 33924