Sailing Vacations at Offshore Sailing School

Quick connect

Bookmark and Share

Sailing Vacations and Sailing Vacation Packages!

Freedom, peace, exhilaration.

That’s what sailing gives you. Book your Sailing Vacations with us. Whether you choose a two-hour sailing lesson, two-day introductory getaway or a three-day or five-day sailing course package that provides certification, you are about to embark on a whole new lifestyle. Discover why learning to sail is inspiring and empowering. Discover how you can sail away as captain of a beautiful cruising yacht in exotic ports, with skills gained at Offshore Sailing School.

Sailing vacations — productive and forever!

You want your next vacation to be productive, fun and lasting. Sailing vacations with Offshore Sailing School are just that!  We offer several sailing vacation schedules.    

If time is a factor and you want to try sailing, you'll love our two-day Introduction to Sailing getaway

Learn to Sail certification is available in our three full or five half-days schedule.

If you want a very special vacation learning experience with a loved one, close friend or the whole family — you can reserve a sailing course, boat and instructor for personalized instruction in our Private Courses for Two or a Private Family Courses programs.  

If you want to start bareboat cruising take our seven-day Fast Track to 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!  Contact us today to learn more.

Take a sailing vacation at a dream resort destination

South Seas Island Resort on Captiva Island is the perfect getaway for sailing vacations– 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 & Marina 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, by beautiful pools and along spectacular Gulf of Mexico beaches.

Scrub Island Resort, Spa & Marina in the breathtaking British Virgin Islands is the sailing capital of the world. Here you are surrounded by incredibly clear azure seas. The resort has gorgeous accommodations, tons of water activities, a three-tiered pool with slide, hiking trails, full-service spa and 24-hour fitness center.

Your 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 sailing, 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.

Is anything more peaceful, more rewarding, or more stimulating than sailing? Enjoy Sailboat Vacations

We think not! Offshore Sailing School founders, Steve and Doris Colgate have been deeply involved in sailing for many decades. More than 130,000 adults and families have gone through their sailing programs since Steve opened his first school in Manhattan in 1964 – a milestone in any industry. The Colgates say sailing is “a lifestyle that reduces your carbon footprint every minute you are under sail.”

Here they are, the ultimate sailing couple, on an Offshore Cruising Club adventure for Offshore Sailing School graduates. "What's not to love about sailing?" they say.

What are you waiting for?
Go sailing for the time of your life!

Call us now at 888-454-7015 or Request a Quote to find out how to book your Sailing Vacation with us today! Our Friendly Sailing Instructors are standing by to answer all your questions!