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Florida Sailing School on Sanibel-Captiva Island, Florida

Captiva Island Sailing at ‘Tween Waters Island Resort & Spa

‘Tween Waters Island Resort & Spa on Captiva Island, Florida, is bordered by vast Gulf of Mexico beaches and the natural beauty of Pine Island Sound.  This popular resort combines historic charm, a variety of amenities, pure relaxation, and water-sports recreation in the best Captiva Island vacation destination.

Sailing with Dolphins and Shoreside Fun

At ‘Tween Waters Island Resort & Spa on Captiva Island, you’ll find the best sailing and boating in protected waters and the Gulf of Mexico. It’s not uncommon to find a dolphin or two playing in your wake or swimming alongside. When ashore, the resort offers a variety of dining options, two pools, tennis courts, and private beaches on the Gulf of Mexico where sandcastle building and shelling are daily activities. There’s also fishing, kayaking, paddle boarding, biking, parasailing, wave running and pickleball to enjoy.

Great Dining Options

Enjoy local delicacies at ‘Tween Waters’ Old Captiva House and Crow’s Nest restaurants, sip refreshing drinks and enjoy snacks at the Oasis Pool Bar while listening to live music, or head to Hideaway, a Caribbean-style pub next to the Serenity Pool. For a special treat, book an island-style dinner at the  new Shipyard  Inn.

The Perfect Island Getaway to Learn to Sail and Learn to Cruise

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.

Basic Sailing Lessons to Big Boat Certification

Florida sailing courses include beginner sailing lessons OSS 101, learn to sail vacation packages, cruising and bareboat charter lessons OSS 103/104/114, and performance sailing courses OSS 102.  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.

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

Shell-Strewn Beaches and Amazing Sunsets

Captiva Island did not suffer the same ravages of Hurricane Ian experienced by Sanibel Island in September 2022. Around this Captiva Island sailing resort are shops and a selection of island eateries that are now open. 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. Accommodation choices at ‘Tween Waters include hotel rooms, suites and cottages.

Protecting Our Planet

‘Tween Waters Island Resort & Spa is part of the Sanibel-Captiva Beach Resorts Collection, and takes pride in protecting and championing our oceans, barrier islands’ ecosystem and environment, and the wildlife and ocean life with which we share our precious planet – as does Offshore Sailing School!

  • Accommodations in hotel rooms, suites, and cottages with Pine Island or Gulf of Mexico views
  • Several eateries on the resort with live music and entertainment
  • Captiva Cruises trips to iconic Cabbage Cay
  • Fishing and shelling guides
  • Kayaking, parasailing, stand-up paddleboards, wave runners, rental boats, and bicycles available
  • Tennis and pickle ball courts
  • Fitness center
  • Birding and dolphin watching
  • Two pools and whirlpools
  • Island shopping on site for fun clothing and souvenirs

Please call 888-454-7015 or email to get a quote for availability in the course you wish to take, and accommodations package costs. Here is an overview of what’s included when you take an Offshore Sailing School course at ‘Tween Waters Island Resort. Please check the individual courses for more details.

An overview of what’s included in the complete course and resort package:

  • Your course tuition
  • Accommodations ashore and taxes on accommodations for all shore stays
  • Per night resort fee if implemented, and taxes
  • 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 textbooks
  • Diploma and logbook
  • Course certification when you pass the test
  • Other items specific to each course

Learn More

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


How to Get to ‘Tween Waters Island Resort

‘Tween Waters Island Resort is in the middle 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:

‘Tween Waters Island Resort & Spa
15951 Captiva Drive
Captiva Island, FL 33924