Much of the charter fleet bases in the northern islands of the eastern Caribbean, but the Tobago Cays are well worth the ride down south.

By Kim Kavin

The Caribbean Sea is bigger than most of us realize. It’s bigger, in fact, than the Mediterranean, but because most of the yachts congregate at the top of the Caribbean, a skewed image of the region’s charter possibilities is the norm. Itineraries often seem limited to the islands above, say, Guadeloupe, because that’s about the distance that can be covered during a one-week charter out of Antigua or Sint Maarten. Clients willing to cruise farther afield can start at St. Vincent and head south into the Grenadines, with the reward being truly memorable anchorages like the one in the Tobago Cays. They’re one of the best-kept secrets in one of the world’s most popular charter destinations.

Here’s the thing to know about cruising into the Tobago Cays: You have to stand on the bow, looking over the side at the clarity of the turquoise water. It’s so unusual in its green and blue hues that even longtime Caribbean cruisers will think, I wonder if we took a wrong turn back at Bequia and ended up in Bora Bora.

Also, it’s imperative to engage in some mental preparation, because the Tobago Cays can be home to yachtsmen who have gone slap-happily native. Up in, say, Sint Maarten, it’s wall-to-wall superyachts with buttoned-up crew, but down in the Tobago Cays, charter guests share the waters with liveaboard cruisers. It’s not unusual for guests on the aft deck of a superyacht to cruise past a deeply tanned man standing full-on naked in his cockpit, blonde dreadlocks blowing in the breeze halfway down his back, waving as exuberantly as a 5-year-old child.

Even the wildlife is different in this part of the Grenadines. The Tobago Cays are a marine sanctuary, so the sea turtles are not only everywhere, but also are huge. Snorkeling alongside them feels almost like seeing nature for the first time, with all the curiosity and joy that implies. The moments are somehow both once-in-a-lifetime and countless, every single day, for as many days as an itinerary allows between stops at Bequia, Mustique and other pearls in the Grenadines chain. Really, 10 days is better than a week here. The extra days allow a more leisurely pace all the way down to Grenada.

This winter is going to be a good time to visit all of these places thanks to a few top-notch charter yachts that have announced availability. Quality charter yachts in the Grenadines are far fewer than in the northern Caribbean, and the stars this winter are expected to include Northrop and Johnson’s Aquavita, which is the only Westport 164 (50-meter) available for charter worldwide. Also 164 feet and heading to the Grenadines this winter is the Benetti Jo, with Camper and Nicholsons International. Burgess Yachts says early word is that 147-foot (44.8-meter) Vitters Lady B will be sailing in the region this winter, while Fraser Yachts Worldwide is promoting 96-foot (29.2-meter) Ferretti Alandrea.

No matter which yacht you book for the Grenadines, when you get to the Tobago Cays, be sure to stand on the bow and look out over that pristine water as you enter the harbor. That memory will stay with you forever. And hopefully, the tan guy’s dreads have grown a bit longer and are now completing the scenic view by serving as a modest toga.