Make the Most of Your Island Time

Go ahead, jump ship, head ashore and you’re sure to find adventure
Go ahead, jump ship, head ashore and you’re sure to find adventure

If you think a Caribbean charter is all about the perfect reach, you might be missing the boat. There’s plenty of fun to be had on shore, so jump ship and find it. Sure, you’ll have a good time at hangouts catering to sailors and pirates, but for a true taste of island life, take a hike. Stroll to a back street, walk the beach, or climb a hill to find that little store full of tradition or a bakery selling johnnycake. Head into a funky rum shop for an earful of political commentary and slapping dominos. Chat up the locals, and what you’ll learn just might surprise.

Every island in the Caribbean has its own cultural flavor and unique personality. If you think you’ve “done” the BVI because you toured Tortola, you’re just getting started. Keep sampling. Little Jost Van Dyke lies decades from the mother island; Anegada stretches a century away to the north. That big gal, Virgin Gorda, is a crazy combo of islands past and future. In the Leewards, St. Barths is a billion euros from sleepy Anguilla, while the buffer between them, St. Martin, offers visitors a split personality with the Wild West Indies on the Dutch side and French country charm on the other. And so on down the chain.

You just never know where a shore trip will lead you
You just never know where a shore trip will lead you

People often ask me to name my favorite island. “For what?” I answer. “What is it you’re after? Beaches, nightlife, food, local culture?” I love them all, each for a different reason, but always because of the people. West Indians, like their music, have a hot, hot spirit and no-problem attitude.

Island pride is a big thing in the Caribbean; everyone thinks theirs is the best but oddly, each is a melting pot. We found ourselves in that cauldron when we drug a vacationing buddy from  a Tortola tourist beach to the real-deal town of Long Look. Wanting to give him a chance to taste the soul of the Caribbean, we wandered into a bar filled with televised cricket and infectious laughter. The customers and owner folded us in; our new BFs from Jamaica, Nevis, Grenada and islands in between. Not one of us was ‘from there’ yet that afternoon we were all Tortolans.

Walk the back streets
Walk the back streets

I began sailing in the Caribbean decades ago, and even though we return to the same places, each visit feels like the first. When our chain rattles out and the hook hits the bottom, I wonder who I’ll meet on shore, what adventure lies ahead.  Some forays, I’m befriended by children or a vendor at the market. I’ve fallen into the middle of weddings and carnival parades. Always, strangers dispense directions and advice and sometimes that’s where the story begins.

One infamous encounter happened in Bequia’s Honeybun Bakery when a local guy entered, announcing, “I NEED A WHITE WOMAN!” Before I could exit, he explained that he needed two ladies, acting as tourists, to join him for the approaching calypso contest. His stage name was Jay Gould and he was after the title of KING.

The King with his GIRLS the day after the big contest
The King with his GIRLS the day after the big contest

It was either curiosity or rum fever that caused me to acquiesce. “Sure,” I said. “I can do that, but what do I wear?”

“Ya whe a beeg hot,” he blurted.  “Ya know, made wid stra. Ya gots ta look like a turst. Like ya layin in de sun!”

On the big day, I joined the other ‘tourist’ he’d shanghaied and together we walked to the high school where Jay Gould paraded us backstage, introducing us as “MY GIRLS, DEEZ MY GIRLS!” He rehearsed the songs he’d written, and I had to admit- he was good. What he lacked in talent was compensated by enthusiasm.

Passing a baptism on the way to shore
Passing a baptism on the way to shore

Out front, a packed crowd was ready to shake the house. The first performance ended with raucous yelling. The second got the crowd on their feet. Jay Gould took the stage and the audience went nuts. While we reclined on stage, he sang his first hip-whining number like a king but it was the next song, the one about the whales, that sealed his fate.

He belted out the lyrics: “If dem whales is dere prop-a-tee, well, tell dem pen dem up!” When he hit the refrain, everyone was with him, jumping and gyrating. It was a hard act to follow and an impossible one to beat. In the end, the crown was placed above Jay Gould’s grinning face; he would move on to the national competition in St. Vincent. My time in the spotlight ended, but his was just beginning.

Although there may never be another Calypso encounter,  I still head ashore with hope. And each time I return to the boat- I’ve got a tale to tell and you will, too. Yes, mon, head in…make a friend, make a memory and make the most of your island time.

Chat up the market vendors for a real taste of the island
Chat up the market vendors for a real taste of the island