Caribbean Voyages

The Windward Islands offer a glimpse of a bygone era for intrepid voyagers.


As our small plane pulled up to the airport terminal on St. Vincent, the propellers sputtered to a halt, and I felt like I had been transported back into another time. Not to the time of pirates and buccaneers that define the early years of many Caribbean islands. But back four decades or so when getting to the Caribbean was still a journey welcomed by rugged voyagers or anyone looking to hide out for a spell. Back to a time when air travel was usually in a creaky old DC-3. Walking off the plane I was smothered by a blanket of heavy, thick August air, peppered with the tropical scents of burning sugar cane and fragrant vegetation. The more I soaked in my surroundings, the more I began to float away into Herman Wouk's Don't Stop the Carnival. The novel about hopeless romantic and philanderer Norman Paperman (can you be both a romantic and a philanderer? Hmm...) who ditched his Manhattan lifestyle to run the fictitious Gull Reef Club seemed alive and I could see how this might have played out multiple times throughout St. Vincent and the rest of the Windward Island chain. And I hadn't even left the runway yet! This was my type of place.

The Windward Islands form the southernmost arc of the Lesser Antilles. They consist of the Grenadines, St. Vincent, St. Lucia, Martinique, and Grenada. Dominica is often classified as both a Windward and Leeward island. Together the Windwards and Leewards make up the Lesser Antilles and, in my opinion, provide some of the most idyllic cruising destinations in the world. Sailors drool over the steady, strong trade winds that combine with a general north/ south orientation to create long reaches throughout the chain. And for powerboaters with a seaworthy craft who have gone as far as The Virgin Islands or St. Martin, I encourage you to go a little farther. The extra effort will repay you in spades.

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Driving down to our motoryacht anchored behind Young Island off the southern tip of St. Vincent, I was struck by the lack of development. In my opinion, this was generally a good thing. I met with local government officials who recognized the importance that yachting played in the region and they were weighing options for the future. But for now, my Don't Stop the Carnival fantasy would remain uninterrupted.

We arrived at our boat just as the sun was setting. The Young Island Resort exemplifies the Windward Island charm with its "barefoot chic" dress code. The 35-acre resort was reportedly named for Sir William Young, the British governor at the time, who traded a Carib chief his horse for the island. Thus the name. It must have been some horse! The resort offers 19 cottages for rent or the entire island can be taken over from about $15,000 to $20,000 per night depending upon the time of year (

South of St. Vincent and Young Island lie the rest of the Grenadines, another island paradise within the Windwards. This chain spans approximately 60 miles and is broken into two "administrative" districts: The northern chain falls under St. Vincent and includes Bequia, Canouan, Mayreau, Mustique, Union Island, the Tobago Cays, and other smaller islands.

Bequia is about nine miles to the south of St. Vincent and is the largest of these northern Grenadines. The island reeks of maritime history and is a must-stop during any cruise. The relaxed pace of the "Big Little Island" is contagious. Shops, galleries, and good restaurants line the harbor and whitesand beach of Admiralty Bay. Be sure to stop by Mauvins Model Boat Shop and Sargeant Brothers Model Boat Shop to see some of the most finely crafted boat models you'll find anywhere. Gourmands won't go hungry on Bequia, or anywhere in the Windwards for that matter. Restaurants serving up a variety of West Indian and Creole fare are plentiful. Having a chicken roti and a cold beer under the shade of a palm at Green Boley is how I began my Bequia experience.

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South of Bequia lies an island that could not be more different and at the same time more similar to the other Windwards. Mustique is privately owned, consisting of about 100 villas, some of which can be rented. I've been to other "private" enclaves that project a 'get off our island' atmosphere. Mustique, however, is charming, gentrified, and welcoming. Be sure to stop by Basil's Bar for some evening libation. This is home of the famous Basil's Blues Festival held every January and February. I've never been, but it is certainly on the list of things to do. Firefly is another dining spot in the hills that is worth the trek. Golf carts are available for rent and a must-have tool for exploring the island.

Watersport enthusiasts will fall in love with the Tobago Cays. These small islands sit within Horseshoe Reef. On the day we were there, the trades blew strong, but the water was sheltered from the reef. This created the most exhilarating windsurfing conditions that I have ever experienced. Needless to say, after a few hours on a board, I was reminded that I was no longer 20. But what a thrill. The snorkeling is world-class, and kiteboarders have also discovered the region.

Development has found nearby Canouan, which now has decent air connections to the rest of the Caribbean and North America. The five-star Raffles Canouan Resort blends nicely into the island setting. The island is complete with a golf resort, shops, yacht club, and restaurants. For me personally, I could hang out all day long in the outer islands, wearing the same swim suit almost every day and not caring if I have a pair of shoes on board. However, I've learned that when cruising with guests, it's a nice respite during a trip to get off the boat and enjoy resort living. Canouan offers just that break. And to be honest, I now enjoy these breaks as well.

So if you're cooped up in a wintery climate somewhere, go grab a copy of Don't Stop the Carnival, maybe put on a little Jimmy Buffet, and think about heading down to the Windward Islands.

Trip Planner Charter Vacations: The Moorings has a base on Canouan with both sail and power vessels. Rent a Villa: Live like a rock star on Mustique.