Best Caribbean Island Cruise | Sail Windjammer | Caribbean Cruise Vacations | Islands

Best Caribbean Island Cruise: Sail Windjammer

This is the Mandalay. A 236-foot schooner with a nose for Caribbean islands that few travelers can even identify. Mayreau. Union. Happy. Those islands. But here's the kicker: There's no real itinerary. On this seven-day Sail Windjammer cruise, Islands photographer Jon Whittle and editor Robert Stephens weren't sure where the captain would be going or what they were about to witness.

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Windjammer | Best Caribbean Cruise | Island Cruise Vacations

The sails are up and the Mandalay is on the move. We’re somewhere in the Grenadines. Headed somewhere amazing. Yes, somewhere.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Mandalay

We board the Mandalay in a protected cove in St. George's, Grenada. On the shore-to-ship tender are 19 passengers, including a magician from Las Vegas, a Russian couple, and a lady on her 23rd Windjammer cruise. Waiting on the Mandalay is a slim, modest man with the smooth skin and life-is-good smile of a teenager. This is our captain.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Captain

His name is Sylvester Dzomeku. “Captain Sly,” he says. He's not a teenager. He's been working the seas since he was 15 — nearly 25 years ago. When asked where we’re going, Captain Sly says, “One rule on the ship: Don’t ask where we’re going. I like to surprise you.”

Robert Stephens

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Sails

The crew hoists the ship’s seven sails during the middle of the night to the tune of "Amazing Grace." A few passengers shuffle up to the top deck, still in pajamas, to watch before going back to their cabins. Where we wake up is anyone’s guess.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Carriacou

“This … is … Carriacou,” Captain Sly announces after breakfast. Anse La Roche, to be exact. This is the quiet end of an island known for its 100 rum shops and one gas station. The crew shuttles a cooler to shore. There’s snorkeling. Lounging. Later, we’ll go for a ride with the captain. Exploring is in his blood.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Carriacou Life

We happen upon 59-year-old William Bethel on Carriacou. Wearing a T-shirt and underwear, he picks guavas for us to snack on. His forearms are chiseled from rowing the handmade boat he uses to fish and dive for food. As it is for everyone on these islands, the sea is his life.

Read about the Best Caribbean Rums.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Grenadine Island

In view of the Mandalay, at all times, is a Grenadine island that’s hard to find on any map. The closer we get, the higher the arm hairs stand. And then we step ashore.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Chatam Bay

Union Island. Most of the passengers drift on floats, dive off the ship and order drinks at an otherwise empty beach-bar hut in Chatham Bay. A few of us follow the captain on a hike to Bora Bora-like spires, where we stop, wipe sweat and gawk. We could stay all afternoon, if only we'd brought some water.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Sunset Sail

The sails go up at sunset. "Amazing Grace" rises from the Mandalay: “My chains are gone, I’ve been set free.” And where she lands? Don’t ask.

Learn about the Best Caribbean Islands to Live On.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Windjammer Captain

The captain sets the tone. Fun. Clean. Full of wonder.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | St. Hilaire

We arrive on Mayreau, an island of 250 people, some of whom are picking sea grapes. “What we have, we share,” says Curtis St. Hilaire, offering a ride in one of Mayreau’s seven vehicles. They even share some of the Caribbean’s most beautiful and under-touched sand.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Island Life

This is Dennis Ford (most Mayreau residents are named Ford). Dennis left the island at 12 to work on a ship. He came back 26 years later to draw Mayreau’s first tourists with its first restaurant: Dennis’ Hideaway. "The property was full of trees and garbage, but I saw hope."

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Empty Islands

We pass islands that have been claimed only by the frigatebirds. “I can tell you we are not going there,” says Captain Sly. “But I do have a special place in mind.”

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Tobago Keys

We anchor off Tobago Cays and take a tender ashore. We eat lunch on the beach. Snorkel with sea turtles. “Come with me,” Captain Sly says. Two of us follow him on a trail, ducking under cacti and hopping over a dry streambed. He stops here, without saying a word.

Discover the Best Islands for Snorkeling.

Jon Whittle

Windjammer | Best Caribbean Cruise | Island Cruise Vacations | Sailing Crew

The Mandalay crew, plus a wayward photographer and editor. Right after this shot was taken, another crewmember fired four shots from the ship’s small rail-mounted cannon. Shots that signified the end of the cruise and the start of new connections.

Book your Sail Windjammer cruise.

Tiffany Sosa

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