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Sailboat chartering in the Caribbean

Updated on April 15, 2013

Vacation of a Lifetime

If you're looking for a vacation you'll never forget, then you should consider sailing the Virgin Islands in the Caribbean Sea. Three of the islands are US territories while the rest are administered by the British.

The Virgins are breathtakingly beautiful. The water is crystal clear and the beaches are pristine white sand. Most of the islands are rather mountainous, while the tropical climate means the foliage is always lush and green.

But the real reason to go to the Virgins is the water and the sailing conditions. It is generally perfect sailing weather.

St. Croix is the largest of the U.S. Virgin Islands but it is some 45 miles from the other islands and is not a popular recreational sailing spot.

Most charter companies are located on either St. Thomas, in the U.S. Virgins, or Tortola, located in the British Virgins.

There are basically two ways you can charter a boat. One is with a captain. Or, if you have adequate sailing experience, you can bareboat charter, which means you take the boat and are the captain and your shipmates are the crew. Then you get to sail when, where and how you want.

All the boats are designed to be self-sufficient for a week long charter. Your sailboat comes stocked with enough provisions to last a week. However, there are plenty of places to anchor and restock if you run short of something.

The boats, depending on the size, can sleep 4, 6 or even 8 people (double occupancy) in relative comfort. The sailboats have shower, cooking and toilet facilities and a fresh water supply, but you learn to conserve fresh water.

When you compare the cost of a vacation for four or six, including room, food and entertainment, chartering in the Caribbean is actually very economical. And you get to see sights with virtually no crowds.

Nothing can compare to sailing down St. Francis Drake Channel, dropping anchor at a secluded beach and snorkeling among the reefs before lunch. Then a rum punch with lunch sets the mood for relaxing under the canopy.

And the most romantic evening you can ever imagine happens when you are anchored in a protected cove, the boat gently rocking, the moon reflecting off the water and the sound of island music drifting across the way.

St. Thomas is a frequent stop for cruise ships and therefore has plenty of duty free shopping. China is a real bargain there. But there are two must see attractions on St. Thomas. The aquarium is actually an underwater enclosure where you are looking out at the fish. They constantly feed the fish so there are always plenty of exotic fish around the aquarium. It is a totally different way to view fish; instead of seeing fish in tanks, you are in the enclosure looking at the fish in their natural habitat.

The other must see attraction on St. Thomas is the banana daiquiri shop. It is located on top of a mountain with a panoramic view of the islands. The ride up to the shop is very winding since there is probably a 1,500 feet elevation rise. And the frozen daiquiris are wonderful. After a couple, you get a little light headed.

St. John's is the other American island in the immediate area. Most of St. John's is a National Park. There are only about 3,000 people living on the island. There is a luxury resort there, Caneel Bay. But you can anchor in the bay, walk the grounds and dine at the restaurants, getting all the atmosphere without paying anything near what the guests there pay.

On the British side, there are two very interesting islands: Peter's Island and Virgin Gorda. There are two must see attractions on Virgin Gorda. One is Little Dix Bay, a luxury resort with The Bitter End Yacht Club. And the Baths at Virgin Gorda is a great place to throw anchor and swim among the huge rocks that jut out of the water.

On Peter's Island is another luxury resort. There is no place to anchor your sailboat so you will need to take a water taxi.

Navigating the Virgins is easy. For the most part you can see your destination. If you are going from one end of St. Francis Drake Channel to the other, it is still rather easy. It is not possible to get lost.

If you have basic sailing skills, you should be able to charter a vessel on a bareboat basis. That way you will have your own floating hotel. And you can go on your own schedule. If not, hire a captain. If you have to hire a captain, talk to him prior to hiring him. It's no fun being on a sailboat for a week with someone you don't like. That also goes for whoever you choose to take with you. Make sure you get along well with them.

There is plenty to do, exploring the islands and the old sugar plantation ruins, snorkeling, swimming or just relaxing. It is a vacation you will remember forever.


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  • Andrew Buys profile image

    Andrew R Buys 4 years ago from Fort Lauderdale, Florida

    Great description for someone considering a private yacht charter. The BVIs are gorgeous any time of year.

  • profile image

    Larry Earl 7 years ago

    One of our favorite BVI locations is a bit out of the way, 15 miles due north of northern sound, Virgin Gorda, is the "drowned land" of Anegada. So named for it's greatest elevation of 28 feet, this 10 by 2 mile wide long island of coral reef islands is a secluded gem of white sand beaches, large salt ponds and unique fauna. The lobster dinners on the beach are unsurpassed. Not every bareboat charter company allows excursions here because the entrance to the horseshoe reef surrounding the harbor can be treacherous. A crewed yacht with an experienced captain may be the best way to make your way to this rare treat.