Sailing the Caribbean in a yacht is the type of bucket-list activity that is far more affordable and easy to organize than people might assume. Although the islands stretch in an arc from off the tip of Florida to off the coast of Venezuela, the sailing areas fall into three main categories: the Leewards, the Windwards and the offshore U.S. islands. Pick any one of these areas and you can enjoy a series of short sails between anchorages. The main sailing considerations to take on board are the hurricane season, which runs from June to November, and places to provision and make repairs, as some islands (St. Maarten and Antigua, for example) are far more yacht-friendly than others.

From the U.S.

During hurricane season, heading south from the East Coast of the United States to the islands involves pitting one’s wits and expertise against frequent storms. The majority of hurricanes and storms that hit pass through Cuba and curve around the Gulf of Mexico before heading east. Sailing legend Don Street recommends heading straight for St. Thomas and skipping a stop-off in the Bahamas entirely. This route provides a better angle for attacking the Gulf Stream. Approach the Lesser Antilles from the Bahamas, and you will be facing strong headwinds that will turn a pleasant sail into a tiring windward beat. The trip from Miami, Florida, is a little more than 1,100 nautical miles. Outside the hurricane season, passages to and between the islands are more predictable, with steady Trade Winds and consistent seas.

Leeward Islands

The Leeward Islands itinerary involves a series of short island-hops among some strikingly different islands, including the British and U.S. Virgin Islands, British Anguilla, Dutch St. Maarten, French St. Barths, and independent St. Kitts and Nevis down to Antigua. With almost constant northwesterly winds, cruising in this area follows a simple path up and down the chain, much gentler on the Caribbean Sea side than the Atlantic Ocean side. For the most relaxing conditions with a following sea, the best bet is to start in Antigua where marine and provisioning facilities are excellent, then head directly to St. Maarten or stop off in St. Kitts and Nevis. From St. Maarten it is possible to visit both Anguilla and St. Barths in two easy day sails. Few areas in the Caribbean offer a better contrast in tempo, culture and activities. Farther north, the Virgin Islands are scattered over a short distance and include some magical smaller islands, such as Jost van Dyke, that are only accessible by yacht.

Windward Islands

The Windward Islands are the southern Caribbean part of the chain that starts in Martinique and ends in Trinidad off the coast of Venezuela, including the popular cruising grounds of the Grenadines and the Tobago Cays. The prevailing winds are east or southeasterly in summer, northeasterly in winter, so the easiest route is to head south, keeping the wind off the beam. Passages between the larger island of St. Lucia and Martinique can be completed in a day, but the big difference between sailing here compared with the Leewards is the greater shift in wind conditions in the passages between islands. The relatively flat Leewards do not interfere as much with wind direction and speed as the steeper ridges islands of St. Lucia, Martinique and Grenada. The safest tactic is to remain within the lee of each island. The majority of cruisers head straight to the Grenadines, where there is a lively cruising community and endless opportunity to potter around the 30 smaller islands teeming with sea life.

Something Different

If the aim is to spend as much time as possible at anchor rather than tackling longer bluewater passages, the Bahamas are perfect. Comprising some 700 islands over 100,000 square miles, the Bahamas present hundreds of isolated, uninhabited cays with turquoise water anchorages and powder sand. The flip side is that yachts need to provision extensively, as self-sufficiency is key off the beaten track. For long passages, hardened sailors can attack the most southerly route from the Dutch ABC islands (Aruba, Bonaire and Curacao) west to Panama. This route is usually undertaken solely for the purpose of crossing the Panama Canal, as conditions are tough. An article by Caribbean Compass observed that “the 400 miles between Aruba and Cartagena ... ranks among the top five worst passages around the world.” The easiest alternative is to focus on the shorter distances between Aruba, Bonaire and Curacao, three delightful islands with great scenery, ample history and well-protected wildlife. Bonaire is all Marine Park offshore, so there is no anchoring.

About the Author

Nick Marshall is a UK-based writer specializing in trends and best-practice in the B2B sector.

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