Sailing Adventure Vacations

It is our pleasure to provide the best possible service and attention you deserve when searching for that ideal sailing vacation. From professional learn to sail classes to individual customized itineraries and more, Sailing Adventure Vacations is here to help you through the entire planning and booking process.

Customizable Itinerary

Learn to sail with our group sailing classes and we will help customize an itinerary that fits your needs

Certified Instructors

Relax in knowing that your Captain or Sailing Instructors are not only certified in sailing instruction, but also experienced life-long sailors themselves.

Make It Fun

We are all about keeping it fun and educational while you - Sail * Learn * Grow

Our knowledge and experience of sailing, combined with years of working and living in a variety of Caribbean locations allows you to have the type of sailing experience you wish

Enjoy Sailing At Its Best

Sailing events are located in popular destinations throughout the Caribbean

Virgin Islands

The U.S. and British Virgin Islands provide the best sailing conditions in paradise to experience the awesome wonders of sailing.  We offer all learn to sail, intermediate and advanced sailing  ASA courses,  instructor training, bareboat charters, crewed charters, and flotilla operations.  We welcome you aboard the ultimate experience for fun and adventure.

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The Bahamas and the Caribbean Sea are well-known for providing a peaceful and stable environment of ecotourism. A Bahamas sailing vacation offers individuals the opportunity to travel along the warm and transparent waters, while discovering and exploring the countless number of cays, coves, and abundant marine life.

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St. Martin

Where else can you experience a sailing vacation which demonstrates two diverse and unique cultures. The island of Saint Martin and Sint Maarten provides such an adventure into old world style European cultures with an added flare of Caribbean culture.

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Belize sailing vacations are extremely popular with many tourists and visitors. In fact, the largest island in Belize, Ambergris Caye and San Pedro Town are said to be the gateway to Belize, by attracting tourists worldwide as a hub for those who seek adventure.

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Flathead Lake Sailing School

Flathead Lake is the perfect place to get your feet wet and test your sailing skills. Known for some of the best sailing winds in North America, Flathead Lake is the ideal location for sailing. Whether you are new to sailing, intermediate, or experienced at the helm, sailing Flathead Lake will provide you with all the fun, excitement, and adventure of sailing.

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About Us

Sailing Adventure Vacations was built with three goals in mind, to build confidence, create a no stress sailing adventure, and to ensure options and choices for future sailing adventures. All classes are structured with your needs in mind! We will always provide a fun, safe and clean learning environment for you.

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Latest News


Become A Sailing Instructor

We are hosting an ASA Instructor Qualifying Clinic


April Spots For St. Thomas Sailing Vacations

There’s still time to enjoy some fun


Sailing Photos Added To The Gallery

  Take a look at the updated sailing



First off I would like you to know that I had a fantastic time at your sailing school. Captain Genevieve was great, very accommodating and a pro. She really seems to know her stuff. I hope to keep in touch with her as a resource and friend as my training advances.


I sailed with VISS back in November 2014. I spent a week aboard the Silver Lining catamaran, with Captain G. as our instructor.   I cannot begin to tell you what an amazing time I had.   I think it must be a tremendous challenge for a captain to teach folks who are coming aboard,

Catamaran Sailing Student - Virgin Islands Sailing Vacation November 2014

My husband and I took the ASA 101, 103, 104 and 114 courses with Captain G in November, 2014. We were on the Catamaran with two other guys we’d never met. By the end of the week, we were a well oiled crew! First and foremost, it’s not a vacation. It’s school, classes, work, studying

Sailing with Captain G - BVI Sailing School Vacation November 2014

Just wanted to drop a note and comment on a great week my girlfriend and I had in the BVIs with Virgin Island Sailing School…and Captain G of course! Captain Genevieve (Captain G) did an outstanding job assisting us with our ASA certifications to enable us to bareboat charter in the future. As a longtime

Brian Milby - Sailing School Vacation British Virgin Islands

Captain Genevieve did a good job of tailoring our trip, May 2015, to suit our past sailing experience (I had a lot – my wife had very little), our future sailing plans, and our laid back attitudes. We got to enjoy plenty of sailing, plenty of exploring, and plenty of rum in one of the

Zach B - New Mexico