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Sailing & Watersports

A group of people riding an inflatable boat in the water.
A group of people riding an inflatable boat in the water.
A group of people on a sailboat in the ocean.

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.

A woman snorkling in the water near a rock.
A group of people sitting on the back of a sailboat.

Life Aboard Your Yacht

Your yacht is your home, your social center, and your classroom. 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.

A group of sailboats docked in the water near a hill.

Sailing as a Fleet

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.

Program 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.

Experiences sailors have the opportunity to play a leadership role on their 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.

Frequently asked questions

None! Many students come with little or no experience at all, but you do need to know how to swim and enjoy being in and around the water. Our captains and mates will teach you everything you need to know about sailing safely and at your own pace.

We offer a huge variety of watersports to enjoy with our trained instructors. Activities include snorkeling, stand up paddle boarding, wakeboarding, tubing, water skiing, wind surfing, and kayaking.

The ASA courses are “challenge courses.” Candidates will learn the theoretical requirements for this certification along with everyone else during our regular sailing instruction. Candidates will participate in a seminars and have opportunities to practice their sailing skills on small keelboats, before being challenged by a practical exam. Free time is built into each camper’s day, so that optional courses don’t take students away from the fun!

If you’d like to take a break from watersports, you’ll have many other activities to enjoy. Share a smoothie with the amazing friends you’ve made, or hop on an inflatable unicorn and soak up the Caribbean sun. Still hungry? Grab delicious healthy snacks in the galley!

Life jackets are worn for all watersports, small boats and even on our 50’ yacht boats while under sail or power. Harnesses are worn during all night sails.