Skip to main content

Secret Charter Spots of the Caribbean

Charter captains reveal their favorite secret Caribbean haunts.

You can always rely on your captain and crew to carve out something special for your charter vacation. While much depends on what you’re looking for, the most successful charter is the one that delivers even more than you expected, where the crew go out of their way to share special places and experiences with you. Here are a few gems from a handful of seasoned charter captains who have been there, done that and truly seen it all.

Capt. Ronald Paxton, M/Y Sixty Six

On Virgin Gorda, we go to Hog Heaven for barbecue ribs, killer rum punch and the best views of the BVI. You can see Leverick Bay, Bitter End Yacht Club, Saba Rock Resort, Necker Island, and on clear days you can even catch a glimpse of Anegada in the distance.

For more information: or any charter broker; 284 547 5964 (Hog Heaven)

 Capt. Paul Stengel, M/Y Plan A

After you leave Nelson’s Dockyard in Antigua, it is really fun to head to deserted Green Island and pull out the water toys: the slide, the paddle boards. There’s a fantastic beach there, which the guests always enjoy. They think they’re in the middle of nowhere, and then I take them by tender to the mainland, to Harmony Hall, an unexpected boutique hotel and Italian restaurant with an art gallery next door. By the time we get back, the crew has the yacht ready to leave Green Island for our next stop, Nevis, where I hire a special guy to take us deep into the rainforest to learn about all of the medicinal properties of the local plants. The guests love it.

For more information: or any charter broker; +1 268 460 4120 (Harmony Hall)

Capt. Brad Baker, M/Y Rena

One less-traveled gem I can think of right off the bat is Trinidad, especially at Carnival time. It must be the most colorful carnival in the world, maybe even better than New Orleans. Another place is in Puerto Rico. There’s an amazing cave—Camuy River Cave Park—about one hour north and west of San Juan. The main entrance to the park is located in Quebrada. This amazing place is a big hit with kids and adults alike. Another adventure I like to take my guests on is a helicopter tour over Montserrat to see the aftermath of the volcano eruption.

For more information: or any charter broker

Capt. James Box, S/Y Gloria

There is fun to be had in Tobago Cays national park, which is enveloped by Horseshoe Reef. The islands that belong to St. Vincent and the Grenadines are designated as a national park. Beach barbecues are regulated, so we call “Mr. Fabulous” and he organizes a lobster picnic on the beach for us. He’ll have a table set up with sunbrellas and cocktails. He brings his own grill and fish (not from the reef), and he cleans up properly.

For more information: or any charter broker; +1 784 492 4056 (Mr. Fabulous)

Capt. Clive Youlton, S/Y Whisper

When we’re in Anguilla, we organize a trip to Scilly Cay, a tiny, coral-based island in the fishing village of Island Harbour on the eastern tip of Anguilla. It’s basically a tiny sand beach. There’s a great Caribbean beach bar, Gorgeous Scilly Cay, with tables in the sand. They cook your fish or lobster any way you want it. You can snorkel after lunch. It’s only open on select days, so call ahead.

For more information: or any charter broker; +1 264 497 5123 (Gorgeous Scilly Cay)

Capt. Zach Wallen, S/Y Jupiter

Barbuda is a beautiful, quiet island with the most amazing pink sand beach. There’s a fascinating Frigate Bird Sanctuary in Codrington Lagoon with 100 or so species of birds, including over 5,000 frigate birds. The males have a distinctive red throat, and it’s cool to go during mating season. I have a local guide there who’ll give us a tour.

For more information: or any charter broker

Capt. Christiana Virgilio, M/Y Big Eagle

Near Young Island off the coast of St. Vincent is a 200-foot-high basalt rock known as Fort Duvernette. The little fort at the top was built in the 1790s. We tender our guests there for a hike to the top. There are many steps to get up there, so our crew brings up the baskets for a picnic and cocktails. Our guests rave about the views of St. Vincent, Bequia and Young Island from there.

For more information: or any charter broker