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Exhilirating Sailing in the Caribbean Windward Islands

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For sailors, the Windward Islands of the Caribbean have long been a dream destination. With strong and steady Tradewinds, warm air and clear, blue waters, sailing here offers the promise of ideal conditions, while island hopping to unique and varied locales.

It was with this promise that we recently sailed a 10-day bareboat catamaran voyage, starting in St. Lucia and finishing in Grenada.

The Windward Islands

The Caribbean region is generally broken down into three groups of islands, the Bahamas, Greater Antilles, and Lesser Antilles. The Lesser Antilles, the easternmost group of islands, are further divided into the the Leeward Islands in the northern part, and the Windward Islands in the southern part. The main islands in the group, Martinique, Lt. Lucia, St. Vincent, and Grenada, form a north to south chain a couple of hundred miles long. Standing apart, and farther east, are Barbados, Trinidad and Tobago.

Each of these island groups are also independent nations, with their own history, customs and culture. Most even have their own dialect of Creole, which is some mix of French, English, and various African languages. With the exception of Martinique, which is still a part of France, they all broke free from their colonial past over a period of a couple of decades in the 1960s and 1970s.

Bushman, the fabulous chef of our beach lobster barbecue in Mayreau
Street Food Wednesday is a highlight in Grenada, with lots of food stalls and live music.

St. Lucia

St. Lucia is best known for The Pitons, conical mountain peaks in the southwestern part of the island. From our first night’s anchorage, they did indeed form a very picturesque backdrop. The rest of the island is also very mountainous, making getting around slow and difficult. Despite this, the tourism industry is well established here, with many resorts throughout the island, as well as a cruise ship terminal.

St. Vincent & The Grenadines

Sailing south from St. Lucia, across 35 miles of exciting open ocean, you arrive at St. Vincent, the largest island and capital of this small nation. Unlike the others, St. Vincent & the Grenadines comprise a group of 32 islands, but only 7 are inhabited. St. Vincent has become known as an upscale sailing destination, with places like Bequia and Mustique catering to the rich and famous.

All of Mustique is in fact owned by its 132 homeowners and non-owners can only come ashore to take a short guided tour or to visit Basil’s Bar and Restaurant. Also in St. Vincent are the Tobago Cays, a group of small islands surrounded by a fringing reef. The clear, shallow waters inside the reef and the sea turtle preserve make this a popular snorkeling spot, with dozens of boats visiting every day.

Grenada

After another exciting passage south, we next reached Grenada, which also includes the island of Carriacou. Known as “The Spice Island”, Grenada features an interior full of lush rainforest and waterfalls, as well as many beautiful beaches. It is also noticeably more prosperous than its northern neighbors. One odd but interesting attraction is the remains of several Soviet warplanes that were abandoned after the US invaded Grenada in 1983.

Locals enjoying an intense game of dominoes
Rain squalls were a daily occurrence. This one in the Tobago Cays included 40 knots of wind.

Barbados

After leaving our boat in Grenada, we took a short flight over to Barbados. Leaving the airport on a modern, multi-lane highway, lined with fancy shops, made it immediately apparent that Barbados is far wealthier than its other neighbors. It seems to be a popular spot for wealthy Brits to have vacation homes.

Unlike the other islands in the Windwards, Barbados was created from coral, rather than volcanic activity. One result of this is that almost nothing grows in the poor soil here, except for sugar cane. Mount Gay Rum, the sailor’s rum, was founded here in 1703 and is the oldest continuously operating rum distillery in the world.

Being sailors, of course we wanted to tour the distillery. Unfortunately, all tours were fully booked for the next week. Undaunted, we drove to the distillery anyway, hoping we could sweet talk our way in. Sadly, the gate guards were not impressed with my Mount Gay regatta hat.

This was close as we got to the Mount Gay Rum distillery tour

Final Thoughts

Our first sign that this would be a different kind of sailing trip was on approach to the St. Lucia airport. Flying low over the water, the ocean was solid whitecaps and the boats we could see were reefed down and fully heeled over. This was not going to be a cocktail cruise!

The good news is that we were smart enough to do a one way charter, with all the sailing being downwind. Thank goodness, because sailing upwind in those conditions surely would have led to a mutiny by the crew and me being keelhauled. If it’s exciting sailing you’re after, in ideal tropical conditions, the Windward Islands offer some of the best to be found anywhere.

We found the head chocolatier at Belmont Estate in Grenada in a tree, picking fruit for his daily chocolate creation
A cacao pod freshly opened

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