When Winter Comes

…SPRING CAN SEEM FAR behind, especially if you live above the frostline and your boat is laid up for the winter. The tropical and subtropical cruising grounds most easily accessible to North American charterers—these include the Virgin, Windward, and Leeward islands of the Caribbean, Florida, the Bahamas, and Belize—are, for the most part, year-round destinations, and it’s undeniably satisfying to escape unpleasant weather back home.

When I’m chartering, I like to poke around ashore almost as much as I like to sail; there’s much history and eco-interest in these cruising grounds. Doing a one-way charter (you pay to have the boat delivered back to the base) allows you to cover more ground). From the top:

Virgin Islands The U.S. and British Virgins are justifiably the most popular charter-cruising grounds for U.S. charterers. The charter infrastructure, honed over the years since its beginnings in the 1960s, combines with the area’s natural attributes—protected waters in the Sir Francis Drake Channel, close-together anchorages and plenty of them, and line-of-sight navigation—to make sailing here about as relaxed as it gets. In the something-for-everyone category, the Virgins offer superb snorkeling and diving, interesting walks, numerous restaurants, and shopping ops. If you’re looking to stretch your sailing legs, charter out of St. Thomas and head south to St. Croix or west to the Spanish Virgins.

St. Martin This French/Dutch island is a convenient hub for exploring the Leeward Islands. A one-week charter will allow you to take in the undeniable charms of St. Martin as well as the splendid beaches of Anguilla and the cosmospolitan atmosphere of St. Barts without pushing too hard. The passages between these islands are short but can be active.

You’ll need more time (about 10 days) to cruise the group of mountainous islands to the south—Saba, St. Eustatius (Statia), St. Kitts, and Nevis. Saba’s two anchorages, Well’s Bay and Ladder Bay (which has some moorings) are totally open to the north. The island is unique, the diving is world-class, and the rain-forest hiking is excellent. Statia has one real anchorage, Oranje Baai, and much history to explore. St. Kitts has a spectacular fort (Brimstone Hill), an architecturally interesting capital (Basseterre), and several protected anchorages in the quiet southern part (a nature preserve), where you can swim and snorkel. Nevis is small, quiet, and picturesque; take a taxi to explore some of the old plantations that have been converted into luxury hotels.

Antigua You can spend a happy week circumnavigating Antigua or add in its sister island, Barbuda. Antigua has plenty of secure anchorages on all sides, and there’s much to see; English Harbour and Falmouth Harbour next to it are renowned sailing centers, and Nelson’s Dockyard and Shirley Heights bring the period of the Napoleonic Wars alive. Quiet Barbuda is known for its outstanding beaches and birds.

Guadeloupe and Martinique These French islands are big and sophisticated; if you’re cruising here, you’ll want to plan for a few great meals ashore. Chartering out of Guadeloupe gives you access to the Iles des Saintes and Marie Galante, both destinations with lots of charm; allot time in Guadeloupe to hike the trails of Basse Terre and visit the waterfalls. Martinique has numerous attractive anchorages on its western and southern coasts and wonderful old plantations.

Dominica, between Guadeloupe and Martinique, has good reason to call itself the “nature island.” Come here for a taste of the old West Indies, and plan to spend some time ashore on the hiking trails and exploring geological oddities.

St. Lucia St. Lucia is an attractive destination in itself—the Pitons have to be one of the most-photographed spots in the Caribbean—as well as one of the gateways to St. Vincent and the Grenadines. Spend time ashore in the rain forest and the walk-in volcano, or join the Friday jump-up in Rodney Bay.

St. Vincent St. Vincent’s charter bases are located in the south of the island and usually serve as a departure point for Bequia and the rest of the Grenadines. Even if this is your plan, save time for a taxi tour of the island, including the botanical gardens (where I was once introduced to the descendent of a breadfruit tree said to have been brought by Captain Bligh himself).

Canouan This island is conveniently located smack in the middle of the Grenadines, probably the most popular destination in the Caribbean chain and home to the well-loved Tobago Cays. The area is not without its hazards—currents, reefs, and rocks demand careful navigation—but the passages between islands are short, the sailing is delightful, and the Grenadine islands are perfect for snorkelers, divers, and interested visitors.

Grenada Tall and lush, Grenada is a rewarding cruising destination in its own right, with lovely anchorages along the south coast. It’s reasonable to include the southern Grenadines in a week’s charter out of Grenada; just going as far as Carriacou will take you to a different world. Be prepared for some blustery sailing if you charter in the early winter (as is true of the Leewards and Windwards in general, where the passages between islands are unprotected).

Belize Belize’s barrier reef, the second-longest in the world, protects its cruising waters. The northern part (San Pedro) has been a diving destination for years, so it has amenities (like restaurants and places to resupply); the southern part (Placencia) has plenty of anchorages, but you’ll have to be careful about water use and the like. Come here for the diving, snorkeling, and fishing (and sailing, of course); extend your stay to explore this fascinating country and visit the exceptional Mayan ruins in Belize and neighboring Guatemala.

Bahamas Chartering here is concentrated in Marsh Harbour, in the Abacos chain. The relatively shallow Sea of Abaco is ideal for catamaran sailing. The towns make for delightful stops, the snorkeling and diving are superb, and the hunt for the perfect conch chowder can be rewarding. Amy Ullrich

Sail Away Archive

Should You Insure Your Trip? (September 2006)

Stormy Weather (August 2006)

Charter a Passage (July 2006)

Less is More (June 2006)

Summer in the Islands (May 2006)

Caribbean Notes (April 2006)

Where to Go Now (March 2006)

Wedding Bells (February 2006)

Charter Cats (January 2006)