Captiva Island - Join the Sailing Lifestyle!
With Offshore Sailing School and South Seas Island Resort
It was in May 1975 that Steve and Doris first drove 17 miles from the causeway to the tip of Captiva Island in search of a Florida home for their winter programs. It had been a long trip: Port St. Lucie on the East Coast, all the way down to Key West, then up to Marco Island. Asking around at the Marriott in Marco, the Colgates were told that South Seas Plantation (as it was then called) would be a great location for the sailing school. When Steve called the General Manager and launched into his “who we are” spiel, he said, “Come on up, I know who you are, we want you here!”
A Premier Year-Round Location 
South Seas Island Resort immediately became a year-round home for Offshore's Captiva Island Florida Sailing School and its premier location: An island surrounded by bays and Gulf waters, blending with lagoon pools and estuaries, and a resort team that insures you will have a delightful, once in a lifetime learn to sail experience!
VisitFlorida.com talks with Steve and Doris Colgate at their South Seas location
Summer and Fall Savings Available

Captiva Island is a great place all year round. In fact, this summer it has been cooler oon Captiva Island then many parts of the United States! Call us at 888-454-7015 to talk Florida sailing vacations with one of our friendly representatives and find out about our summer and fall specials too.
What about the kids? We haven’t forgotten them, and neither has South Seas. Two clubs - one for youngsters and the other for teens - exude accomplishment and self-confidence along with a major dose of learning and fun activities. And our Kids and Teens Learn Free Captiva Island sailing courses, give you and your family a lifelong pursuit and bonding experience unlike any other.
South Seas Island Resort lies on the north end of Captiva Island with miles of sandy, shell-strewn beaches. It has a par-3 executive golf course, state-of-the-art tennis courts, and miles of running and bicycling paths, lagoon fis
hing, kayaking and more. Manatees play in the Yacht Harbour where the Offshore Sailing School fleet resides. Dolphins jump through our bow waves as you sail in the Sound and out in the Gulf. Captiva Island Vacations are truly a unique experience.
Here, virtually all of Offshore Sailing School’s courses are available. If it’s certification you seek, all our core courses provide this validation, with a stair-step progression that gives you good reason to return year after year for more sailing in Florida.
Where are you in your sailing confidence and knowledge? Haven’t tried it yet, or feeling too rusty to take the helm? For any of these reasons, a three or five-day vacation combined with our signature Learn to Sail course takes you right through the Intermediate level. You’ll Learn to Sail or renew your skills on our easy to sail 26-footers designed for fun, fast sailing and your safety and success in mind.
Know how t
o sail but want to sail faster, and more efficiently? We’ll give you the go-fast techniques you always wanted in Performance Sailing; then when you’re ready to race, join our Offshore/North U. Performance Race Weeks and go home a winner! Or you can take our Fast Track to Performance Racing and combine the two courses in an exciting sailing vacation and Captiva Island sailing experience.
Want to go cruising some day – cross an ocean or just enjoy grand times exploring your own backwaters? We’ll take you from our 26 footers to the helm of a big cruising boat in Fast Track to Cruising® - a super getaway that gives you three certifications in one week.
If you already have basic skills or have taken our Learn to Sail course, you’re ready for Captiva Sailing Bareboat Cruising Preparation (stay ashore at the resort) or Live Aboard Cruising (live aboard while learning). Either of these will prepare you for cruising your own boat or chartering in paradise. And if you want blue-water experience, you can then go into our Fast Track to Coastal Passage Making course.
If you'd like an introductory experience, our Two-Day Learn to Sail getaways and Weekend Bareboat Refresher adventures are both informative and fun. Two-hour sailing lessons are fun and informative outings for those already enjoying one of our Captiva Island Florida sailing Vacations.
Offshore Sailing School’s Corporate Sail-Race Challenges® make every meeting relevant. You’re busy, you’re special – South Seas and Offshore understand. We can put together a program for your team that takes as little as half a day and produces amazing results.
What about the kids? We haven’t forgotten them, and neither has South Seas. Two clubs - one for youngsters and the other for teens - exude accomplishment and self-confidence along with a major dose of learning and fun activities. And our Kids and Teens Learn Free Captiva Island sailing courses, give you and your family a lifelong pursuit and bonding experience unlike any other.
If you are looking for a premier destination resort, exclusive to its guests, with the best sailing learning vacation option there is – choose South Seas Island Resort and Offshore Sailing School on Captiva Island, Florida. Week-long and weekend schedules are available to create the perfect Captiva Island, Florida, sailing vacations.
Or call 888-454-7015 to talk to a friendly sailing advisor about our Captiva Island vacations.
Click here for directions to Captiva Island
View Offshore Sailing School Locations in a larger map