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Watersports & Island Excursions




You don’t need a scuba tank to explore what’s going on below the waves. With just a snorkel, mask and fins, you can watch from the surface as the undersea world shimmers with action. Stingrays, pufferfish, whooshing shoals of silversides, and even the diving pelican make appearances. Learn about the strange creatures making their homes in the deep.

stand_up_paddleboardingStand Up Paddleboarding

Get a totally fun core body workout while surrounded by nature. Learn to propel and maneuver with perfect balance. You’ll find out why this sport is rocketing in popularity. Ask your Mate to show you a few yoga moves on a board. Maybe you’ll even master Warrior stance!


It started out as ‘skurfing’, a combination of skiing and surfing born in New Zealand. Now it’s popular everywhere; especially at Sail Caribbean! It’s your turn to pop off the wake and catch some air!


It’s bright red and yellow, it’s full of hot air, and its name is Paparazzi! If you’ve got a passion for excitement, you’ve just got to try this out. This is tubing to the max. You’ll be hanging on so tight you won’t even be able to give a thumbs-up.


Getting up for the first time might take a few tries, but once you’ve got the hang of this sport you’ll be hooked. Racing across the water and learning to jump the wake makes for a thrill a minute.


There’s no better way to explore the gorgeous coastline than from the cockpit of a kayak propelled by your own paddle power. You might even want to challenge a friend to a kayak race and give those biceps a workout. Kayaking is what you make it, a leisurely paddle or an exercise adventure.

small_boat_sailingSmall Boat Sailing

Less is more, so swap your 50-footer for a sailing dinghy and get close to the water. Try a Laser, Hobie Cat, or one of our Pico’s or Colgate 26.


This is minimalist sailing for sure…just you, the rig and the wind! Our instructors will have you carving jibes across the bay in no time or at least sailing across the anchorage.


Island Excursions

Since Columbus, explorers have been amazed by the natural beauty and variety of the Caribbean islands. Now it’s your turn. Hike through a rainforest or to the top of a volcano. Spy on exotic tropical birds that live in the colorful foliage. Ride the narrow winding hillside roads of St. Barths with a breathtaking bird’s eye view around each turn. Learn about the art of glassblowing, watch a demonstration, and see the beauty of the finished products produced. Visit an organic farm and taste the fruits of the islands. Find your own special place to watch a sunset. You’ll see why the islanders cherish their part of the world, meeting unique characters born from a melting pot of cultures.


Whether you’re at Norman Island, Virgin Gorda, Saba, or Sage Mountain, you can bet that your tropical sunset hike is going to deliver a spectacular view of turquoise waters, white sandy beaches, and green lush islands. At Salt Island, you can look out on the exact spot where the RMS Rhone ran aground and sank to her current resting place. The Sage Mountain trail will make you feel like you’re in the middle of a jungle from which you’ll be able to look out on all of Tortola. At the Baths you’ll follow a trail that winds around, through, and over massive boulders. You’ll learn about the geologic formation of the islands and why the Baths is such a different experience.

social_eventsSocial Events

There’s no shortage of opportunity to meet new people. We travel as a fleet, so when we go ashore you’ll meet the crews and staff from the other boats. During the day the beach is alive with games and the anchorage is full of activity. As the sun goes down there could be a barbecue, we might hit a local restaurant for dinner, or dance at a beachside disco. In the BVI, there’s the Fireball Party at Trellis Bay complete with Moko-Jumbie stilt walkers, a local band, and artfully constructed fireballs. To wrap it all up, the group faces off for honor and glory at the Sail Caribbean Olympics, a time-honored tradition that’s a highlight of each program.

While on docks and at various mooring fields, you’ll have the opportunity to do a little shopping and buy some souvenirs to bring home to friends and family. We’ll also go out to eat dinner or just some dessert and tropical drinks from time to time. Nothing cools you down like a virgin Pina Colada!

Beach Activities

We may live on a boat, but that doesn’t mean we can’t appreciate the joy of a true beach day! Our beaches and the shallow waters off them are perfect for watersport games. Test your talents with a group synchronized swim, ultimate water frisbee, or a circular volleyball battle.We’ll have picnics and BBQs and always leave time for a game or two of football, volleyball, soccer, or Frisbee. Bring a book and find a cool spot in the shade where you can relax to the sounds of the tide lapping against the shore.