Captiva Island Vacations, Florida

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Captiva Island Sailing School

Captiva Sailing at its best!

Have you run out of ideas for how to spend your next upscale vacation? If you love vacationing in the outdoors, it’s not enough to say that you want an adventure-themed getaway. Now it’s time to book a different kind of vacation and embark on a whole new lifestyle. 

A Premier Year-Round Location 

We encourage you to try a southwest Florida vacation at the beautiful South Seas Island Resort where you will have the time of your life! It’s the perfect getaway, an escape to Captiva Island, Florida. Let us show you how to put the wind in your sails. Read more to discover why our sailing school, situated along one of the most pristine beaches in the eastern U.S., is so popular.

Captiva Island is known for conservation and protection of wildlife, which means that you and your family can get very close to nature when you’re not in sailing school. On your next vacation to Captiva, enjoy the shell-strewn, sandy beaches of Captiva Island. Book a sailing adventure through our Florida Offshore Sailing School.

"Amazing location to learn to sail!" – Matthew Wagner - Sanibel Island, Florida 

There are unique advantages that we provide every client, regardless of age, when visiting our Florida location. Our top-notch instructors give each participant a first-class sailing education. They are experts in sailing education with certifications to reflect their experience.

We also help serious sailors obtain their desired certifications and easily join the ranks of our 130,000 satisfied graduates. Plus, if you’re serious about sailing, we can help you get on the fast track to cruising, with a life-changing program that opens the doors to more sailing vacations. 

For Beginners

  • Learn to Sail is our beginner’s sailing certification course on safe, comfortable and fun to sail Colgate 26 sailboats – completed in 3 whole days or 5 half days
  • If you have limited time, a 2-day introductory sailing experience is a great way to test the waters
  • Fast Track to Cruising® is the quintessential learning experience, no prior sailing experience required as you will go from novice to navigator and earn three certifications in a week 

Cruising and Performance Courses for Intermediate Sailors

  • Captiva Sailing Bareboat Cruising Preparation Certification course – 5 days learning aboard a 43' Jeanneau while living ashore in resort accommodations
  • Live Aboard Cruising Certification Course – 6 days living aboard a 43' Jeanneau while gaining the skills to cruise on your own or charter big cruising sailboats
  • If you want to go beyond the intermediate daysailing level, a three or five-day Performance Sailing cOffshore Sailing School Jeanneau 439 sailboatsourse is full of go-fast and safety techniques

Racing and Passagemaking for Advanced Sailors

  • Performance Racing – an intense 7-day course with expert coaching that gets you ready for serious sailboat racing
  • For blue-water sailing, our Fast Track to Coastal Passage Making course and Fast Track to Offshore Passage Making courses cover navigation and passagemaking skills in 6 to 10 days

Programs for Corporate Groups

Our sailing curriculum would not be complete without our Corporate Sail-Race Challenge®. This is the perfect way to build members of your corporate group into a team while offering them a quick one-day getaway or the comforts of resort accommodations. Our programs are tailored for your employees and you, ranging from a half-day, full day or multiple days working together on the water. We guarantee amazing results!

Programs for Teens and Youths

The best part about booking a family vacation is that kids can learn to sail free with their parents. Here are comments from a March 2012 family course at South Seas Island Resort on Captiva Island.

"Our experience with Offshore Sailing School exceeded my hopes and expectatons. Our instructor was so good at breaking down the steps for all of us. I was amazed at how much information my 10 year old and 12 year old retained! He was very patient and kind to them."
Jeff Cross - Denver, CO

During your Captiva Island sailing vacation, consider sojourning at the South Seas Island Resort, located on the north end of the island. This resort features a par-3 executive golf course, state-of-the-art tennis courts, miles of running and cycling paths, lagoon fishing, kayaking, a sea school, and more!

Manatees play in the Yacht Harbor around our Offshore Sailing School fleet. Dolphins jump through the waves as you sail in the Sound and out to the Gulf of Mexico. Captiva Island vacations are one-of-a-kind and best experienced on one of our 26-foot sport sailboats or 43' cruising yachts.Colgate Offshore Sailing School at South Seas Island Resort

History of Our Captiva Island Sailing School

To trace the history of the school, we must go back to May 1975. This was when Steve and Doris Colgate discovered Captiva Island and decided it was the perfect place for winter sailing programs. They had quite a long trip and many considerations as they traveled from Port St. Lucie on Florida’s east coast all the way down to Key West before returning up the southwestern coast to Marco Island.

Asking around at the Marco Island Marriott, the Colgates learned that South Seas Plantation would be ideal for a sailing school. When Steve called the general manager and offered his best introduction, the gentleman replied: “Come on up. I know who you are. We want you here!”  And the rest is history. South Seas Island Resort became the year-round location for our Florida Sailing School! 

Get Started Now - Call 888-454-7015

An Offshore Sailing School 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 a love of the water and 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 get started on your Captiva Island Sailing Vacation. Our Friendly Sailing Advisors are standing by to answer all your questions!