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Sail Caribbean Sailing Adventures



No Experience Necessary!

If you’ve never set foot aboard a 50′ sloop, it’s OK with us. At Sail Caribbean, sailing is a breeze and you don’t need any prior knowledge. Most students who join our summer adventures have just a little sailing experience and some none at all. You just need to love being in and on the water! We start from square one and you’ll learn while doing – it’s a true hands-on process with our staff by your side. It won’t be long before you’re speaking the lingo and working the yacht like a seasoned sailor; hauling, winching, tacking, and jibing. Once you’ve tasted the thrills, challenges and camaraderie of sailing, you’re sure to become a fan. We guarantee you’ll gain confidence with each new accomplishment.



Life Aboard Your Yacht

Explore More: Learn About Life on Board

Your yacht is your home, your social center, and your classroom. It’s a modern, 50-foot, single-hull sailing yacht (or a 45-foot catamaran on the Foxtrot, Tango, Sierra, & Ocean programs). Whether you’re just learning port from starboard, or looking to expand your sailing skills, you’ll have a high-performance craft, an experienced captain and mate as constant companions, and enthusiastic crewmates to share the adventure of sailing Caribbean waters.

Small and Large Groups

We travel in fleets of 2 to 6 boats depending on the sailing adventure. You’ll enjoy both the close camaraderie of your crew, and the opportunities in being part of a larger group. During daytime watersports or beach activities, and evenings in quaint island towns, you’ll have plenty of time to make friends with students from other boats—exploring, playing, eating and dancing together.

More than just safety in numbers, sailing as a fleet enables the mates on our staff to rotate from boat to boat, sharing their own unique knowledge and energy with each crew. Each of our staff has an interesting personal background. They have been school teachers, dive instructors, tall ship crew, ski patrol veterans, marine science researchers, and volunteers who have traveled the world contributing their effort and time to causes they believe in. All take a genuine interest in the lives of teenagers and are excited to tell you about themselves and learn all about you too.

You’ll race the fleet from island to island, gaining practical experience in right-of-way rules and racing strategies. But your boat is not always part of the fleet. Itineraries also include independent days when the fleet breaks into smaller groups and the students determine their own schedule, activities, and anchorages.

Because you’re sailing with other boats as a fleet, you’ll have plenty of opportunities to make lots of new friends. Fleet living provides a balance between the best of both worlds: the close friendships with your own crew and the social diversity of a community of teenagers who have different goals and interests and come from all over the US and abroad.

  • Your yacht is your home
  • We’ll teach you the ‘ropes’
  • Live with a co-ed crew that’s your age group
  • Learn teamwork and leadership
  • Stay in sight of land while cruising through BVI
  • Explore the islands we visit
  • Become responsible for running the boat
  • Sail as a fleet for more social opportunities
  • Earn sailing certifications

Programs for All Ability Levels

Sailing may seem tricky at first, but you’ll learn sailing basics quickly by getting involved. Your staff members onboard give sailing instruction, while keeping everyone safe and comfortable. Within days, you’ll have a handle on the basic principles and theory and you’ll know when to trim, ease, head up, or bear off. Sailing a yacht will also teach you teamwork, planning, and responsibility. The rewards are a sense of achievement, an appreciation of nature, and thrills you’ll hardly find anywhere else.

You have an opportunity to play a leadership role on your boat as the rest of your crew gets comfortable learning the ropes. Small boat sailing is different than captaining a 50’ boat, so even with prior experience you will be learning new sailing techniques and teamwork skills every day.

Browse Advanced Programs

Sailing Certifications

We have Sail Caribbean’s custom designed Crew, Bosun and Mate certifications to advance your knowledge and skills. Challenge yourself by taking the ASA 101 Basic Keelboat course available on Alpha, Bravo, Delta, & Echo, or take it a step further with ASA’s 103 Basic Coastal Cruising course on Bravo, Delta, and Echo or ASA 104 Bareboat Cruising on Echo.

Sailing Certifications

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Sailing Adventures