Caribbean Escape


This winter, escape the ice and snow by jetting south to the Caribbean for a week or two of charter.  There is nothing like a week or two in the sun and warmth of the Caribbean for chasing away the winter blues and restoring your spirit. The Caribbean has so much to offer and a wide variety of cruising grounds. Here’s a look at six of the favorite locations to take a winter charter vacation.  (published December 2015)


baths    The  U.S. and British Virgin Islands are so well laid out for sailing and chartering, they could have been designed by the charter companies and built by Disney as a marine theme park.

In the U.S. Virgins you can sail out of St. Thomas and explore the many harbors and coves around the island and nearby St. John. There are great places to eat, good snorkeling and fun hikes in the hills.

Or you can head west to the Spanish Virgins and explore Culebra and Vieques where the beaches are perfect and the Puerto Rican influence spicy and raucous.

In the B.V.I., you will find dozens of tempting spots to cruise and some famous beach bars to visit. There is the  new Pirates and the Willie T at Norman Islands, The Bitter End Yacht Club in Virgin Gorda’s North Sound and the famous Foxy’s and The Soggy Dollar on Jost Van Dyke. Or you can chill in the quieter anchorages and swim and relax the week away.


Beautiful tropical beach on St Martin Caribbean
Beautiful tropical beach on St Martin Caribbean

The Leeward Islands of the West Indies, from Anguilla south to Dominica, are a chartering Paradise with hundreds of anchorages and plenty to do ashore. For North Americans, St. Martin and Antigua are the most often used islands for starting a charter in this section of the Caribbean since that is where the largest charter bases are located.

From St. Martin you can be lazy and just poke around the islands visiting both the French and Dutch sides and sampling the many bistros, bars and night clubs ashore.  Or you can head out to Anguilla where the beaches are perfect and the diving around Sandy Cay some of the best in the area.  Southward, you can visit Isle Forche, where the harbor is in the caldera of an ancient volcano and then sail to St. Barths to sample the Caribbean’s swankiest destination. Here the food is wonderful and the people and yacht watching unparalled.
Gustavia harbor, St. Barts, French West Indies
Antigua is an island long favored by sailors and it was here in the years after the Second World War that the Nicholson family invented the Caribbean charter trade. The islands remain a sailor’s haven and a great place to charter. You can poke around the island for a week or make the short passage north to Barbuda where the beaches are amazing and the solitude total. Or you can charter during Antigua Race week and enjoy one of the winter’s most fun regattas and parties.

The Windward Islands of the West indies are famous for boisterous sailing, amazing islands and some of the Caribbean’s finest reefs. From charter bases in St. Vincent, you can head south to Bequia where shipwrights still build wood sailing vessels and the locals take part in an annual whale hunt.

Union Island, Saint Vincent and the Grenadines
Union Island, Saint Vincent and the Grenadines

From there you sail south to the Grenadines. Mustique might be the first stop but you may not be able to anchor and go ashore if the British Royals or other jet setters are there since it is a private island. On southward, the Tobago Cays are the gems of the region and the diving is spectacular. You’ll find plenty of places to eat ashore and explore on Canuoan, PSV and Union and your might get all the way down to Carriacou before returning to St. Vincent.

For cruisers who have explored the wide world, the Grenadines remain one of the planet’s best cruising destinations.



Like Antigua, Grenada is a sailor’s island with several charter bases and lots of anchorages to explore. You can cruise around Grenada for a week quite happily while you explore the beaches, the beach bars and the many good restaurants.  The hiking in the mountains takes you through lush jungles and nutmeg plantations and leads you to tall waterfalls where you can swim on hot afternoons.

Or, you can sail northward to the southern Grenadines, sailing by the infamous Kick’em Jenny  —an active underwater volcano—and make landfall at Carriacou. From there you can explore the Tobago Cays.

Grenada’s capitol St. George’s is one of the prettiest towns in the Caribbean and home to good restaurants, shops and a classic fort from
the days of the Napoleonic wars.

Belize    The Central American nation of Belize is home to the world’s second largest barrier reef. Inside the reef the sailing is in fresh trade winds but flat water. There are hundreds of anchorages, reefs to snorkel over and famous places to visit like Lighthouse Reef and The Blue Hole.

The islands are not all that developed so chartering is more rustic here than in the rest of the Caribbean. You will eat aboard some evenings and will find that the beach bars are scattered around the cays. You go to Belize to enjoy the diving and snorkeling and to be amazed by the coral formations and the abundance of tropical fish.


Ashore there are rain forests to explore—eco tourism—and ancient Mayan ruins to visit. The country is well set up for tourists and charterers and offers a winter sailing vacation unlike anything else you will find in the Caribbean.


Author: Blue Water Sailing