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Caribbean, the Real Deal

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 the 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 nothing or a
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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 the 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 nothing or a bakery that serves rotis and johnnycakes. Head into a funky rum shop for an earful of political commentary and slapping dominos. Chat up the locals, and what you’ll learn won’t come from a guidebook.

Every island in the Caribbean has its own cultural flavor and a unique personality. So 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. Barts is a billion euros from sleepy Anguilla, while the buffer between them, St. Marten, offers visitors a split personality with the Wild West Indies on the Dutch side and country charm on the French side. And so on down the chain.

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 a no-problem attitude.

Island pride is a big thing in the Caribbean; everyone thinks theirs is the best. But oddly enough, each island is a melting pot. Recently we found ourselves in that cauldron when we dragged our new-to-the-tropics sailing buddy away from the Trellis Bay tourist beach to Tortola’s real-deal town of Long Look. Wanting to give him a chance to taste the soul of the Caribbean, to meet the people who have inspired us to sail there again and again, we wandered into a little bar/snack shop/hangout where several customers and a lady behind the bar were having too much fun. The place was filled with sound from a televised cricket match and their infectious laughter—and not one of our new acquaintances was a Tortolan. Together we limed away the day, laughed hard, learned that cricket is a complicated game, and left with a story to tell.

I began sailing in the Caribbean 30 years ago, and even though we always 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. Each time I row back to the boat after a shore excursion, I’ve got a tale to tell—and you will, too. Yes, mon, head in…make a memory, make a friend, and make the most of your island time.

On our third day at Jost Van Dyke I rowed ashore with a grocery list, intent on replenishing our fresh stores. I walked the length of the town on the main road, a one-lane track in the sand. Passing five bars, the customs house, a tiny stone church, and a herd of goats, I followed signs to Rudy’s Rendezvous Grocery, nestled behind Rudy’s Mariner Bar. At two in the afternoon it was closed. The next day at eleven it was closed again, so I went searching down a back street, not far from the icehouse. As I approached I saw three local women on the porch, two of them engaged in a hair-braiding session, the third one shelling pigeon peas in her lap. “Good afternoon, ladies,” I greeted.

“Afta-noon, madam. How you?” one asked.

“I’m fine, thank you,” I replied. “How about you?’

“Blessed, my dear. Blessed today.”

The pigeon-pea sheller followed me in, taking her proprietor’s spot behind the wooden counter.

“I’m looking for fruits and vegetables,” I told her. She pointed beyond me toward a wall of deep wooden bins holding…one onion. Nothing more. “Do you have anything else?” I asked.

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