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Caribbean Sailboat Charter

A Caribbean Sailboat Charter is an outstanding Vacation. With warmth almost year-round, the Caribbean is an ideal vacation destination with something for everyone. Relax. You will have a crew on a charter sailboat. Sometimes the crew is two persons: a Captain and a Chef/Steward. And other times, you could have three or more crew members depending on the yacht’s size, which can mean higher service levels.

Just climb aboard and set sail; no need to worry about finding your way around or running out of food or drink. Family Fun, kids love sailing because it’s not just a boring old boat ride. They can do all sorts of things, like watch the captain steer, explore onboard, swim off the side if they feel brave, or you can even attend cooking classes while onboard. All around, a Caribbean sailboat charter is a fantastic vacation.

There are two popular types of Sailboats for your Caribbean Sailboat Charter. One is a traditional sailboat; as you can imagine, this is formally referred to as a “Monohull.” Having 1 “mono” hull typically allows the vessel to sail faster overall; however, it does lean over “sometimes fairly dramatically.” It is exciting to feel the wind on your face while marveling at how the boat moves.

On the one hand, this makes for a more authentic and traditional sailing experience; however, it can be a bit cumbersome. The second and more popular sailing boat to charter in the Caribbean is a “Catamaran.” Unlike the more traditional sailboats, a catamaran has two hulls and is a bit wider. Due to the catamaran’s design, they are typically more spacious and much more stable when sailing. It’s almost inevitable that you’ll feel like you’re on a floating condo.

Some of the top Caribbean Sailboat Charter Destinations

An Entire New Adventure

Sail to a new destination every day as one destination blends with another. All in an ever-changing landscape that promises a new exploration each time. You’ll be taking it all in knowing you are on a crewed yacht. There are so many excellent snorkeling spots that it’s simply too many to list here!

Smooth Sailing

With so many unique destinations to choose from in the Caribbean. Maybe you’ve been wondering what makes the BVI so popular. The British Virgin Islands offer many protected anchorages and little open ocean sailing. The islands form a ring that helps keep the higher waves and swells out of the general sailing area. The sailing here is World Class.

Plenty to do in The BVI

Sip on a Painkiller at The Soggy Dollar. Located on the famous Jost Van Dyke in the BVI, you’ll find the Soggy Dollar. The Soggy Dollar is world-renowned, and for a good reason. The setting is perfect, with distant views of the other islands, such as Tortola. This is a great spot to anchor and swim on the white sand beach for their staple “Painkiller” concoction. Their name is derived from an event; swimming to the beach with money in your pocket.

Also located on Jost Van Dyke is the very famous or “infamous” Foxy’s bar and grill. All year round, Foxy’s draws many people seeking a perfect beach bar scenario. However, New Years’ eve is when this place gets going with its infamous “Old Year’s Night Party.” One of the most happening places in the world aboard a private yacht!

In addition, the BVI is known for scuba diving, with many wrecks, caves, and reefs to explore. Check out these seven Amazing BVI Dive Spots.

Check out this always “live” webcam of Soggy Dollar bar

United States Virgin Islands “The USVI” | Caribbean Sailboat Charter

Convenient Caribbean charter destination

Several factors make the USVI a more convenient sailboat charter destination. For US citizens, no passport is needed since the USVI is a US territory, Just like Puerto Rico. Another factor is that, unlike most other Caribbean destinations, St. Thomas has direct flights from the New York City Airports, Charlotte, Orlando, Atlanta, and Miami.

Explore new cultures | Caribbean Sailboat Charter

Spend a day or a week exploring what our Frenchtown base has to offer. These range from the Emancipation Garden, where enslaved people were freed to Blackbeard’s Castle, a national historic landmark on St. Thomas.

Explore St. John – USVI

St. John is surrounded by crystal blue waters, tropical foliage, historic ruins, and many beaches, perfect for snorkeling or simply relaxing in tranquil solitude. Experience natural beauty amid modern luxuries at St. John’s unspoiled beaches like Trunk Bay, a popular snorkeling spot known for its crystal sands and underwater nature trail. Explore the culture and history of St. John.

Plenty to do in the USVI

From the countless excellent snorkeling spots to the St. John hiking and the unique and fun Pizza boat. You will have plenty to do on your Caribbean sailboat charter in the USVI! Here’s a link to anchorages in the US Virgin Islands.

Other Leeward Islands; St. Martin/St. Maarten, Anguilla St. Barths, and more

You’ll find unparalleled beauty and adventure when you take a sailboat charter to the Leeward Islands. This vacation destination is halfway down the eastern Caribbean chain islands, including Nevis, St Kitts, St Bart’s, and St Maartin in the north; Antigua and Barbuda in the middle; Montserrat and Guadeloupe to the south.

Sailing vacations offer everything, including majestic tropical landscapes, powdery white beaches, sparkling waters, one-of-a-kind cuisine on St Maartin island, and lively nightlife on Antigua island. Nature lovers will love visiting St Kitts and Nevis, where both islands are crowned with spectacular cloud-ringed peaks covered with tropical forests and brilliant flowers.

Windward Islands

Caribbean Sailboat Charter
Piton peak, St. Lucia

Sailboat charter in the Windward Islands Sprinkled across the southern Lesser Antilles, stretching from Martinique to Grenada, the stunning Windward Islands blaze a trail of powder-white beaches and crystalline waters.

Lying in the southeastern Caribbean in the path of the northeast trade winds, Barbados, Trinidad & Tobago, Martinique, St Lucia, St Vincent, and The Grenadines, and Grenada are known for their tropical scenery, stunning beaches, remote anchorages, and hidden coves: all the ingredients for a perfect yacht charter.

Volcanic and rugged, adorned with lush scenery and surrounded by whimsical reefs and cays, this excellent yachting destination benefits from the proximity between these islands. Those seeking secluded anchorages, excellent dive sites, and sublime island beauty will not be disappointed with this little slice of paradise. So which island of the Caribbean is best for you and your next Sailboat Charter? Call us, and we will happily help you sort out any of your Caribbean yacht charter questions…

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.