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Sailing School on Sanibel-Captiva Island, Florida

Captiva Island Sailing at ‘Tween Waters Island Resort & Spa Colgate 26 and Leopard 40 catamaran

‘Tween Waters Island Resort & Spa on Captiva Island, Florida, is nestled between 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 adventurous 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, delicious dining, two pools, perched on the Gulf of Mexico where sandcastle building and shelling are daily activities. There’s also fishing, kayaking, paddle boarding, biking, parasailing, wave running, pickleball, and much more.

Yummy Dining Options

Enjoy scrumptious local delicacies at ‘Tween Waters’ Old Captiva House and Crow’s Nest restaurants, sip refreshing drinks and enjoy snacks at Oasis Pool Bar while listening to live music, or tuck away at Hideaway, a Caribbean-style pub next to the Serenity Pool.

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!

Perfect Island Getaway

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.

From Basic Sailing Lessons to Big Boat Certification

Florida sailing courses include beginner sailing lessons, learn to sail vacation packages, cruising and bareboat charter lessons, and performance sailing courses.  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

Around this sailing resort are many shops and a fun selection of island eateries. 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.

Accommodations include hotel rooms and suites and quaint cottages. If you want to explore and shop off the island you may want to rent a car.  Add another day or two 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, 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 the course and accommodations package. 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:

  • Your course tuition
  • Accommodations ashore and taxes on accommodations for all shore stays
  • Per night resort fee and tax during your stay ashore
  • 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

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