Great Sailing Vacations!
Freedom, peace, exhilaration.
That’s what sailing gives you. Book your Learn to Sail Holidays and Sailing Vacations with us. Discover how learning to sail is inspiring and empowering. This is what we hear from our customers – every day.
You want your next vacation to be productive, fun and lasting. A sailboat vacation with Offshore Sailing School is just that! If time is a factor and you want to try sailing, you'll love our two-day Learn To Sail and weekend Learn to Cruise getaways. Pick any two days you like and really learn something new at a friendly seaside resort.
If you are traveling alone, you'll find new friends with similar desires in our programs. If you want a very special vacation learning experienceon your next Learn to Sail Holiday with a loved one, close friend or the whole family — you can reserve a course, boat and instructor for personalized instruction in our Private Courses for Two or a Private Family Courses programs.
Learn to Sail in two to three days or five, then take a cruising course and set your sights on a lifetime of sailing vacation adventures. The freedom and peace you gain through sailing is unequaled. The thrill of accomplishing new skills, the fun that comes with spending quality time on vacation, priceless!
Is anything more peaceful, more rewarding, or more stimulating than Sailing? 
We think not! Offshore Sailing School founders, Steve and Doris Colgate have been deeply involved in sailing for many decades. More than 115,000 adults and families have gone through their programs since Steve opened his first school in Manhattan in 1964 – a milestone in any industry. The Colgates know sailing is “a lifestyle that reduces your carbon footprint every minute you are under sail.”
Here they are, the ultimate sailing couple in adventure mode, circa 1989 leading a sailing vacation for graduates in the (then) Yugoslavia. They are still actively running the company and taking their graduates on sailboat vacation cruises all over the world. "What's there not to love about sailing?" they say.
In May 2010 they will lead two more adventure cruising vacations, this time in the Caribbean. And yes, sailing keeps you young! Take a course soon and you’ll qualify to join them in celebration of two major anniversaries: Offshore Sailing School’s 46th year and Steve and Doris Colgate’s 40th wedding anniversary.
Choose two days or more.
Take a Sailboat Vacation at a dream Florida resort.
South Seas Island Resort on Captiva Island is the perfect sailing vacation getaway – 365 acres of secluded Gulf beach and bay property with golf, fishing, bicycling, jogging paths, tennis, private cabanas by the pool and shell-strewn beaches.
Pink Shell Beach Resort and Spa on Ft. Myers Beach is at the island’s quiet end, a short walk to hopping nightlife, fun stores and dining. Relax at the resort's Aquagene spa, pools and spectacular beach on the Gulf.
Your Discover Sailing Vacation Getaway combines a special sailboat vacation learning experience with plenty of time to relax and enjoy everything else there is to do, too.
Dolphins play in your wake, manatees hover nearby. If you choose a mini-vacation with two half-days of sailing, you'll enjoy a Sailboat Vacation that's fun and flexible to fit your busy schedule. Whether you choose two days or a more comprehensive learning vacation experience, we’ll book your accommodations at our exclusive low partner rates. Bring your kids, a spouse or friend . . . and your appetite for sharing more quality time together. Or just come alone and enjoy the camaraderie of others with similar goals.
You can't beat any of Offshore Sailing School's value-packed learning experiences, such as Learn to Sail Holidays, starting at just $395 per person, plus accommodations at our low partner rates.
What are you waiting for?
Go sailing for the time of your life!
Click here to contact us and learn more about our Sailing Vacations or call 888-454-7015 today!