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A Cat Can Take You There: the Grenadines

In the archipelago, between St. Vincent and Grenada—there are approximately 600 islands and islets in total. Both St. Vincent and Grenada are home to charter operations so you can approach the vacation from either end...

September 1 marks the beginning of lobster season in the Grenadines. I’ll never forget that, because it was on September 1 that I ate a most unforgettable lobster.

It came out on a massive platter: a half-dozen fire-red crustaceans piled high, served beside mounds of steamed vegetables and fried plantains, all placed on an old splintery picnic table where I sat, barefoot on the beach. As my crew and I dug in, the skinny proprietor grinned and sang a song called “Big Bamboo” while our charter catamaran bobbed peacefully at anchor behind us. “Black Boy,” as he called himself, was the cook, the waiter and the entertainment. The only other customers on the beach that served as his “restaurant” were the French crew of the other charter boat in the anchorage. The meal was so strikingly genuine, so Caribbean, that I am still torn between telling everyone and telling no one, torn between sharing it and keeping it all to myself.

Moments like this can be found everywhere in the archipelago between St. Vincent and Grenada—approximately 600 islands and islets in total. Both St. Vincent and Grenada are home to charter operations, so you can approach the vacation from either end. Some companies will even allow you to sail a one-way trip. Click to view map.

Whatever itinerary you choose, don’t rush. Be sure to allow two full weeks for this charter. You’ll want to be able to build in extra days for those moments when a man from Mayreau like Black Boy appears and offers to entertain you for a few hours.

A word of advice, though: set reasonable expectations. This is not Florida, nor is it the British Virgin Islands. This is the heart of the Caribbean, and on many islands, things like cell service and refrigerated provisions are hard to come by. Mooring balls are policed by locals in sketchy dinghies, and beach bars are almost always cash only. There are no major grocery stores, and petty crime is not uncommon. You don’t need to be worried, but you do need to be careful. Knowing that, you can unplug, unfurl and enjoy your time in the Grenadines.

St. Vincent

If you begin your charter in the north, it will likely be out of Blue Lagoon. Boats are kept on mooring balls or at the docks, and the area provides plenty of provisioning options. There’s a lovely white-sand beach, and Young Island, which is mostly private with excellent beachfront restaurants, is a short dinghy ride away. If you choose to spend a day on St. Vincent, sail up to Petit Byahaut and snorkel at the famous Bat Cave, where you can swim in one side and out the other. Spend the night at anchor and travel ashore to enjoy the small beach and the tiny restaurant at the base of picturesque hills.


In many ways, Bequia embodies the transition between the old and new Caribbean. The northernmost Grenadine, its main drag has a handful of souvenir shops, bars and restaurants, but they’re interspersed with brightly painted ramshackle houses and rustic boatbuilding shops that produce local craft to a design dating back centuries to the island’s Scottish ancestry. There is a “beachfront boulevard,” which is actually just a tiny strip of beach, at times a foot wide, that connects the bars and restaurants along the coast of Port Elizabeth. Admiralty Bay is an easy place to clear customs, and there is plenty of room to anchor on either side of the well-marked shipping lane. If you want to stay the night away from the madness, drop anchor off Princess Margaret Beach in the South of Admiralty Bay, where you’ll find good holding and a lovely beach.


Mustique is the exception that shatters that rule about adjusting your expectations. The tiny island was purchased in 1958 by a wealthy British aristocrat, Lord Glenconner, and turned into a cotton plantation. When that failed, Glenconner divvied up the land into 120 properties and sold them to an eclectic group of socialites, rock stars, designers and artists who all wanted to be a part of this exclusive and pristine Caribbean getaway. Today these properties are private and rental villas—beautiful, exclusive homes that can be enjoyed for an arm and a leg. For visitors, there’s also one hotel, one guesthouse and one beach bar (Basil’s Bar), accessible from Britannia Bay where moorings cost upwards of $65/night. The whole island is utterly pristine, with the best-kept topiary you’ve ever seen, and it’s well worth your while to take a tour with a local driver who can point out the homes of the rich and the famous, including Mick Jagger, David Bowie, Tommy Hilfiger and the late Princess Margaret, to whom Glenconner gifted a plot as a wedding present. Customs is inconveniently located at the airport, in the middle of the island, so as long as you’re driving, you can stop at Macaroni Beach, described as one of the “Sexiest Beaches in the World.”


Canouan is also a mix of old and new Caribbean. The main anchorage and mooring field, Charlestown Bay, was once home to a Moorings base and is now mostly run by a local named Marcus who services the moorings and also delivers water and fuel on request. On shore, the northern half of the island has been converted into a high-end Italian resort, offering visitors a day of relaxation at the Amrita Spa or a round of golf at the Trump International Golf Course. The rest of the island—where you’ll find your fellow charter brethren—maintains its original Caribbean charm, and is known for its great hiking and snorkeling. After a meal at the Tamarind Beach Hotel, spend some time strolling the beaches, hiking Mount Royal to enjoy a spectacular view of the surrounding islands, or snorkeling on the impressive lagoon on the windward side, which is surrounded by a colorful coral reef.


Unlike Canouan and Mustique, there is no airstrip on Mayreau, so you have to get there on a boat. As such, the island remains untouched, genuine and wildly Caribbean—the kind of place where the likes of Black Boy feel right at home. The preferred anchorage here is Salt Whistle Bay, which is everything an anchorage should be: crescent-moon-shaped, protected on all sides, peaceful, and surrounded by perfect white sand beaches dotted with coconut palms. One narrow strip of beach is home to the infamous Salt Whistle Bay Club, a sailors’ favorite. Unless you’re lucky enough to show up at one of Black Boy’s parties, you’re not likely to see many people on this quiet bit of paradise, just evidence that they live there: a tiny church at the crest of Station Hill, a cemetery, a school and a small shack with the name “Honour and Glory Souvenir Shop” printed above its entrance.

Tobago Cays

There are a handful of memorable places you visit in a lifetime that instantly secure a spot on your “Best of” list. The Tobago Cays are that sort of a place. A cluster of five tiny islets just a few miles from Mayreau, the Tobago Cays are both a National Park and a turtle sanctuary, meaning there are government-run boat and dinghy moorings and a ban on fishing to protect the reef and marine wildlife. The effects of this protection are dramatic: the snorkeling is colorful, diverse and gorgeous, with too many turtles to count. Above the water, the islets are all a short dinghy ride apart, and you can easily spend a day beach-hopping, enjoying the uninhabited sandy beaches and searching for wildlife; box tortoises, hermit crabs, iguanas and bird life abound. At night, the southern sky envelopes the Cays in a blanket of stars unspoiled by light pollution, and the only sound you hear is the chatter of neighboring sailors, who are also in awe of the place. Here you’ll appreciate the shoal draft of your charter catamaran: channels between islets are shallow and should be carefully navigated. Unfortunately, the Tobago Cays are far from undiscovered, so be sure you arrive in plenty of time to grab a mooring ball. Then settle in and let the place infest your mind.

Union Island

Compared to the tranquility of Mayreau and the Tobago Cays, Union Island feels cosmopolitan. Its main town, Clifton, sits at the heart of the southern Grenadine sailing industry and has a number of shops, markets and docking facilities. On shore you can hike nature trails, peruse the multiple beaches or bike along the winding roads while perpetually being greeted by friendly locals. The best gem is found in the middle of the reef off Clifton. Here a creative local entrepreneur named Janti has collected bushels of the island’s discarded conch shells, piled them up on the shallow part of the reef, added a couple of palms from nearby Palm Island and christened the place “Happy Island,” where he serves snacks and rum drinks. Access is only by dinghy, payment is only in cash, and it’s only open when Janti feels like it. It’s a treat you’d only find in this part of the world—just ask well-known food critic Anthony Bourdain, who featured Happy Island in his show “No Reservations”.


Carriacou is locally considered a “large” island, but is still only 13 square miles, which helps put the region in perspective. Similar to Mayreau, it has managed to avoid the onslaught of tourism that has plagued much of the Caribbean and instead has preserved its island charm. The locals trace their ancestry back to Africa, which lent them a lively music tradition, and Scotland, which accounts for the rich boatbuilding tradition. Between the two, things are vibrant on Carriacou, and there are several great excuses to visit throughout the year: Panang (the annual Christmas celebration-cum-Battle of the Bands); Carriacou Regatta (both a race and celebration of boatbuilding history) and Festival (one of the best in the region) top the list. Carriacou, from the ancient Amerindians’ “Kayryouacou,” means “Land surrounded by reef” and for sailors, the list of sheltered anchorages with great snorkeling is exhaustive. Anse La Roch in the south offers scenic beaches and beautiful coral reefs and Tyrrel Bay on the southwest shore is utterly picturesque. The town of Windward offers a view into the island’s boatbuilding past, while the capitol Hillsborough has enough shops and restaurants to make for a fun visit, but also enough colorful shacks and characters to remind you that you’re in the heart of the Caribbean.


It’s almost a shame that charter companies make their base on Grenada, because it’s all too tempting to toss off the lines and use it only as a casting-off point. While Port Louis in St. George’s, the capital, is indeed an excellent place to provision and maintain charter boats, the city and countryside offer so much more, it’s definitely worth taking a couple of days at either end of your trip to explore. The possibilities are exhaustive: shop in True Blue Bay, hike to the top of Mount Maitland in the awesome Grand Etang Forrest, dine in St. George’s, admire the colonial architecture of the town’s churches and streets, stroll miles of white sand on Grand Anse Beach, visit a chocolate factory (ask Horizon Yacht Charters about its chocolate tours), tour a rum distillery or get lost in the rolling hills and crater lakes that are home to thousands of plant and herb species, giving Grenada its well-earned title as “The Spice Island”. Water sports are abundant as well, as the island is surrounded by beaches for combing and reefs for diving. Consider visiting during the Grenada Sailing Festival when the island comes alive to celebrate its seaborne past.

Charter Resources

Barefoot Yacht Charters, Blue Lagoon, St. Vincent,

TMM Yacht Charters, Blue Lagoon, St. Vincent,

Dream Yacht Charter, St. George’s, Grenada,

Horizon Yacht Charters, True Blue Bay, Grenada,

The Moorings, St. George’s, Grenada,

Sunsail Yacht Charters, St. George’s, Grenada,





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