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Sailing the Grenadines

In 2015 we and some friends chartered a sailboat with a skipper in Guadeloupe. The skipper, a Frenchman named Denis, who had seen the world several times over, provided us with an enthusiastic commentary as we sailed from Guadeloupe to Marie Gallant and Les Saintes. But we wanted to know: What was his favorite place to sail?

“Ooooh,” he replied, “les Grenadines sont les plus belles, les meilleures des îles des Caraïbes.“

This lived in the backs of our minds as we set out on our sailing adventure, and while we were at first overwhelmed, we soon grew to appreciate the wisdom of Denis. Yes, we agreed, after sailing up and down through them, the Grenadines are the best of the Caribbean islands.

Stretching from Grenada in the south to the island of St. Vincent in the north, the Grenadines comprise 22 individual islands (not all inhabited). They jut raggedly from the ocean, irregular and distinctive, each proclaiming its individuality, separate voices. Now, as we make our way back to Grenada for the summer and wrap-up our sailing season, it’s time to reflect back on each of our stops in these special places.


Though Carriacou is politically part of the country of Grenada, it is geographically part of the Grenadines. It was the destination for our first big sail (32 nautical miles) when we left Woburn Bay on December 1st. And it was where we returned as we headed back to Grenada for the end of the sailing season. Like Bequia, Carriacou is a very walkable island. To supplement walking, it also has the same convenient bus service found on Grenada.

Tyrell Bay, where we anchor, is big without feeling vast, and there are two marinas and a Budget Marine store along the waterfront. And there is a proper supermarket with real food in it, too. There are some restaurants and bars, but not too many, giving it a laid-back, folksy feel. It’s a great place to come and drop out.

Union Island

Union was a mixed bag for us. Clifton Harbour was the first stop after we left Grenada heading north. The clearing-in process was, humbly, a bunch of baloney. It was done not through customs and immigration, but through an agent, who was also supposed to do a health screening. Incoming cruisers were supposed to take a mooring ball, which a boat boy would lead them too. Of course, all this cost money. We were irked when the boat boy, who is supposed to be paid by the agent, tried to double-dip us for more. Sure, it’s only a few bucks, but don’t pee on my head and tell me it’s raining.

We moved immediately to Chatham Bay, which was delightful and peaceful—except when the wind gusted to over 40 knots and snapped our snubber in the middle of the night. (More on that in my previous blog post, “Santa’s Flatulence and the Naked Celtic Sailors”:

We stopped on Union Island once more on our way down, to clear out of St. Vincent and the Grenadines, but we vowed not to anchor in Clifton Harbour. Instead we dropped the hook behind Frigate Island, and it was lovely. Even with some wind the anchorage was smooth, and we could watch the kite surfing school students as well. Clifton Harbour was less than an hour walk when we went to clear out (this time only with customs and immigration—no agent B.S.), and we treated ourselves to one of the best meals we have had while cruising, at Sparrow’s.


We stopped in Bequia twice, and we were enchanted by its beauty and its people both times. Admiralty Bay has lots of room to anchor, plus a floating bar. The colorful houses pop from the hillsides, as if Paul Gauguin himself had passed through here on his way to Tahiti. (Close: He spent time in St. Pierre, Martinique.)

We arrived the first time on the Winter Solstice. Admiralty Bay was busy for the holiday season, and for a specific reason. It has become tradition for Scandinavian sailors in the Caribbean to gather there for Christmas. The tradition started some years back when a Swedish couple sailed into the bay, looked around, and decided they would make it their home. They began inviting other Scandinavian sailors to stop there for Christmas, and it caught on. The result is now scores of boats flagged in Denmark, Sweden, and Norway filling up the anchorage over the holidays. It makes for a festive and lively international crowd.

The next time we stopped in Bequia was in April, on our way down. It was as lovely as we remembered. One of the things we love is the village feel Port Elizabeth has to it. Front Street is lined with small shops and bars and restaurants. And there is a walkway along the southern edge of the bay called the Belmont Walkway that leads to Princess Margaret Beach. (Yes, it’s named for that Princess Margaret. Apparently this was one of the places she loved to swim naked.) And Bequia is a small enough island so that it is easily walkable, which is good therapy for cruisers cloistered aboard 40-foot sailboats.

Tobago Cays

The Tobago Cays were a unique and unforgettable experience. And, it turns out, a crowded experience when we were there. It fills up midweek with charters, making for a busy spot. But it is visually stunning, and anchoring is between reefs in waters for whom the word “turquoise” was invented. We swam with turtles and oodles of other reef fish.


Mayreau is a small island just north of Union Island. The people are among the friendliest we have met. We spent some time with Maurice at Wine & Things, chatting about how he can expand his wine bar business. And since we were there over Easter, we attended mass at the Catholic church, located on the highest spot of the island. The bishop was the guest padre, and he ministered to an overflowing crowd of sailors.

We anchored in Saline Bay—Salt Whistle Bay is purportedly the desired spot, but it is always full, and we had a nice walk over there, where we met a friend from Bequia, and were treated to an incredible fish lunch from Larston, one of the restauranteurs there. As lovely as the people of Mayreau are, their island would benefit from the spirit of Vermont’s Green Up day, a state-wide, community-driven effort to pick up trash every year. It was the only negative thing during our stay there.


The other magic of the Grenadines is the sailing itself. The islands are no more than a half-day sail from each other, allowing sailors to mix-n-match their experiences. Once in place, it's easy to slip away from the Tobago Cays and head over to Union for dinner at Sparrow's. Or get up to Bequia for a regatta. Or head over to Mustique for the blues festival. (We did not have time to stop and explore Canouan and Mustique.) The winds are always fresh and the currents are challenging, but when you drop anchor behind Horseshoe Reef and there is nothing but the Atlantic Ocean and some breakers in front of you, well, as Stephen Stills sang:

You understand now why you came this way

Cause the truth you might be runnin' from is so small

But it's as big as the promise, the promise of a comin' day.

For now, the Grenadines will occupy one of the most exciting chapters in our memories of sailing this year. But the distinct characters of each island, whether visiting or sailing by, will stay with us no matter where our camino takes us.

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