Martinique and the Grenadines Sailing Itinerary: An Eleven-Night Cruise to Saint Lucia, Bequia and the Tobago Cays

The waters south of Martinique open onto one of the most celebrated cruising grounds in the Caribbean: the chain of islands and islets that runs down through Saint Lucia, Saint Vincent and the Grenadines toward Grenada. Trade winds blow steadily from the east for most of the year, filling sails on comfortable reaching courses between islands that are rarely more than a few hours apart, while calm, turquoise anchorages give sailors of every level a chance to relax between passages. It is a region built for sailing: consistent wind, short hops, and a string of protected bays that reward those willing to leave the marina behind.

Passages typically run between fifteen and thirty five nautical miles, comfortable half day sails that leave plenty of time to arrive, anchor and explore before the light fades. The channels between islands can build a short, occasionally lively sea, particularly crossing from Saint Lucia into the Grenadines, but once in the lee of an island the water flattens and the sailing turns into easy, downwind cruising. The rhythm settles quickly: mornings under sail, afternoons at anchor, with enough slack in the schedule to wait out a squall or linger an extra hour over a good snorkelling spot.

The landscape shifts from island to island: the volcanic peaks and forested slopes of Saint Lucia give way to the low, scrub covered hills of the Grenadines, where white sand cuts a sharp line against impossibly clear, pale blue water. Bequia's Admiralty Bay offers a wide, well protected anchorage backed by a lively waterfront, while the uninhabited cays and reefs further south, culminating in the Tobago Cays, are as close to postcard Caribbean scenery as sailing gets: a scattering of sandy islets ringed by a horseshoe reef, with turtles grazing in the seagrass just off the boat.

Ashore, the character of the islands changes as often as the scenery. Saint Lucia and Saint Vincent carry a strong Creole and British colonial heritage, visible in weathered fishing villages, small rum shops and markets selling the morning's catch alongside local produce. Bequia has long been a whaling and boatbuilding community, and its waterfront still has the unhurried feel of a place that has welcomed sailors for generations. Union Island and the smaller Grenadines feel more remote again, with beach bars, a handful of small restaurants and a slower pace that suits a crew happy to swap sightseeing for swimming and simply watching the light change over the water.

Life on board follows the sun: an early swim before breakfast, a morning passage with the trade wind on the beam, lunch at anchor in a quiet bay, then an afternoon free for snorkelling, a walk ashore or simply reading in the cockpit before the evening meal. Evenings are unhurried, spent over a sundowner watching the anchorage fill with other boats, or ashore at one of the small beach restaurants that dot the more popular bays. It is sailing paced for enjoyment rather than mileage, with the flexibility to stay an extra night somewhere that feels right and press on quickly through anywhere that does not.