Let the Wind Be Your Guide: The Top Charter Sailing Vacations

Windward Islands: Sailing in the other Caribbean

Sooner or later, you'll tire of the Virgins and think of exploring other Caribbean cruising grounds. Rest assured, that instinct is well informed. For confirmation, head to the more rugged Windward Islands, from St. Lucia in the north to Grenada in the south, which offers some of the finest sailing in the West Indies. St. Lucia's Anse des Pitons is one of the most spectacular anchorages in the world, with sugarloaf-shaped peaks towering 2,000 feet above the ocean. Anchoring is quite a challenge, for there is 600 feet of water only 400 yards from the beach. You should anchor 50 yards offshore and secure a stern line to a nearby tree.
From Anse des Pitons, most people sail south to Blue Lagoon or Young Island at the southern tip of St. Vincent, before taking off for The Grenadines. The prevailing trades allow you to reach comfortably down-island, even if the inter-island passages can be a trifle bumpy. Coming home, you'll be hard on the wind, so allow plenty of time to work your way up north.

Start by sailing down the westerly side of the islands, spending your first night at Bequia, only about nine miles from Blue Lagoon. Admiralty Bay, near the main town, is a fine anchorage, and there are simple restaurants ashore. No visit to Bequia is complete without an excursion to Friendship Bay and the island of Petit Nevis off the south coast.
Most charterers head south from Bequia to Tobago Cays and Union Island. Tobago Cays consists of four islands inside Horse Shoe Reef. Avid snorkelers spend days here, either anchored off Baradal Island, or in the narrow cut between Petit Rameau and Petit Bateau Islands. You can walk ashore and admire the aloes, collect shells on island beaches, or simply snorkel for hours on end. Nearby Palm Island, Union Island, and Petit St. Vincent offer a pleasant mix of island resorts, with the best anchorage in Clifton Harbor sheltered behind the reefs, just off the resort hotel.
From Union Island, it's a comfortable day's run south to Grenada, a superlative cruising ground by any standard. The best anchorages are along the southwestern coast, so plan to visit St. George's first. This is a good shopping town, and the public market on Wednesdays and Saturdays is always a treat. The Dutch-style architecture of the town is well worth a leisurely tour. The southwestern coast is a gunkholer's paradise with many sheltered anchorages. The anchorage west of Hog Island is among the best. At Hog Island, you eyeball your way between reefs, conning the ship from the bow through brilliantly clear water. Once inside, anchor in about twenty-five feet of water, and use your dinghy to explore the channel into Clarke's Court Bay and to snorkel local reefs. Most sailors work their way as far east as Bacaye Harbor, having explored many secluded anchorages like Port Egmont. The reefs are tricky here, so enter the harbor when the sun is high so you can detect changing water colors.
Practically Speaking
The best time to sail here is between November and April, when the northeast trades blow steadily at a constant 15 to 25 knots. Most bareboat charters in the Windwards start in St. Lucia or St. Vincent. From St. Lucia you can anchor in Anse des Pitons on the first evening of your charter.

Paul McMenamin is the author, editor, and photo director of the original Ultimate Adventure Sourcebook.

Published: 1 Feb 2001 | Last Updated: 15 Sep 2010
Details mentioned in this article were accurate at the time of publication


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