Island Time

It's impossible to rank these favorite destinations by beauty. Instead, sailors should set a waypoint based on what they want to experience

- LEXI FISHER

From Martinique to Grenada, the Windward Islands trace the border of the southern Caribbean Sea. They include four countries, dozens of islands-many of them uninhabited-steady trade winds, and hundreds of miles of navigable coastline. This tropical playground is an ideal sailing destination for seasoned sailors and first-time charterers alike.

At the northern end of the Windwards is Martinique, the only French territory of the group. With its fine wine, boulangeries and chic Paris fashions, it's the island where resisting indulgence is hardest. It's also a major yachting destination with skilled technicians, though it's often the most expensive. Colorful colonial architecture dots the coastline, and cafes and restaurants line the beaches.

St. Lucia's mountainous coastline beckons to the south of Martinique, with tourist destinations such as the Pitons bringing well-deserved fame. Diving and snorkeling can provide equally spectacular views underwater. There is no shortage of all-inclusive luxury resorts and romantic retreats, especially in the area around the Pitons.

St. Vincent and the Grenadines, by contrast, is where sailors get away from the crowds. The west coast of the St. Vincent mainland is rural, secluded and steep, making anchoring and mooring a challenge. Almost no yacht services are available, except at the Blue Lagoon Hotel and Marina at the southern end of the island.

From there, sailors can leave the mainland behind and head south to the Grenadines for idyllic turquoise Caribbean water. Sandy, uninhabited islets speckle the horizon. The Tobago Cays are on par with the Pitons as far as cinematic vistas, and are the destination for charter yachts.