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Sailing Lessons at South Seas Island Resort

A rewarding sailing vacation on Captiva Island

Offshore Sailing School has offered sailing lessons at South Seas Island Resort since 1975. Steve and Doris Colgate, Offshore Sailing School founders consider South Seas "our top saling vacation destination for teaching adults and families the joys of sailing."

Many different sailing instruction courses are offered at this unique southwest Florida location, for beginners, intermediate and advanced level sailors. Three to seven-day courses which provide certification, and a two-day introductory program, are packaged with accommodations at the resort. So working with Offshore's knowledgeable saies associates is a seamless process in choosing what you want to learn and where you want to stay.

Please call 888-454-7015 for packages
And your South Seas Island Resort course discount

Or you may use the quick-connect on this page. Course schedules and pre-requisites are described below. In most cases we suggest you extend your vacation an extra day - leave the morning after your last day in the course.

When you are ready to sign up please give your sales associate the code "SOUTHSEAS50" and you will get a $200 per person discount on Learn to Sail and select Cruising courses listed below.

Please see the "rules" at the bottom of this page for discount code use. All courses are conducted with a maximum of four students per instructor per boat, except in special cases where you may "buy the boat" for a maximum of six learning together, or choose the Kids and Teens Learn Free program.


Learn to Sail in three full days

This is a fast paced schedule, designed for those with short vacation goals and a desire to absorb all there is to learn quickly. You can take the course Monday-Wednesday (arrive Sunday, depart late Wednesday) or Friday-Sunday (arrive Thursday and depart late Sunday). Each day you are in class and on the water from 8 a.m. to 5 p.m. with a break for lunch.

Learn to Sail in five half-days

This schedule allows a half-day free to relax, spend time with family and friends, enjoy other resort amenities and explore the area. It is ideal for couples and families who want to learn together. Plan to arrive Sunday afternoon and depart late Friday. 

If you are traveling with others who already know how to sail but want to move up to bigger boats and gain cruising skills, the five-day schedule is the same for both courses. Some in your party can take the Learn to Sail course and at the same time others can take the Bareboat Cruising Preparation course, allowing free time together. 


This is our signature course - an exclusive way to go from "couch to the captain's chair" in seven days. The course starts with the first two days of the three-day Learn to Sail course on a Colgate 26, followed by the five day cruising course on a Jeanneau 439 (shown here). For the cruising portion you may stay at the resort throughout or live aboard the yacht (see choices below). Fast Track to Cruising is the most comprehensive and rewarding experience you'll find, culminating in Bareboat Cruising Certification. Plan to arrive Friday afternoon and depart late the following Friday (or extend your vacation an extra day so you don't have to rush). No previous sailing experience is required.


If you have skills equivalent to our Learn to Sail course, this five-day cruising course taught on one of our Jeanneau 439s prepares you for big boat ownership or bareboat chartering. It is taught in five half-days on the same schedule as the five-day Learn to Sail course. Plan to arrive Sunday afternoon, start your course Monday morning, and depart late Friday after you test sail. While taking this course you will stay in your choice of accommodations at the resort.


Everything taught in this course is the same as in the Bareboat Cruising Preparation course, but in this case you spend only your first night (Sunday) at the resort and the rest of the time living aboard the Jeanneau 439, learning while cruising from port to port. The course ends at noon on Friday and that afternoon you set off with your classmates on a test cruise, returning the boat before noon Saturday. Learn to Sail or equivalent experience is required to take this course.


Sailing Lessons and Two-Day Intro to Sailing

If you just want to get a little sailing in, we offer two-hour sailing lessons for just $75 per person per hour, with  two hour minimum.Though not a certification course, the two-day Intro to Sailing allows you the opportunity to gain some sailing knowledge and enjoy the resort while on the water three hours hours each day.


Performance Sailing

This is the next step up from Learn to Sail for those who want more experience on a high performance boat like the Colgate 26. It covers go-fast and more safety techniques. You may take this course on the same schedule as the Learn to Sail course.  Learn to Sail or equivalent experience is required.

Performance Race Week

This program is a joint venture between Offshore Sailing School and acclaimed North U. - for sailors with some racing experience who want to move up to the winner's circle. Some call it "boot camp" for racers, but all say it is the most rewarding learning experience they've had. Plan to arrive Sunday evening for the meet and greet and spend the next six days on the water in drills and actual races with an instructor-coach on each boat.

Passage Making Courses

When you are ready for blue-water cruising, several courses are available to give you the skills to sail over the horizon. These programs start with four days ashore in navigation courses, then continue with six days of non-stop sailing before returning to the resort.

Call 888-454-7015 to get your new lifestyle going!

The Fine Print:

  • Code SOUTHSEAS50 required to activate $200 per person discount
  • Available only on Learn to Sail, Fast Track to Cruising, Bareboat Cruising Preparation and Live Aboard Cruising courses
  • Cannot be combined with any other discounts or offers
  • Not available on "buy the boat" or "Kids and Teens Learn Free" family courses
  • This discount may be changed or discontinued at any time