Go Ahead: Make a Plan. Now Try Sticking to It

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I was in my late 20s, working in book publishing and broker than broke, when I first dove into the Caribbean. Mexico’s Isla Mujeres, Cozumel and Playa del Carmen were sleepier then than they are now, and I had never seen water so turquoise, strolled sand so soft, or quaffed beer so deliciously cold. Each day, I baked on the beach, cooled off in the sea and read a whole book. Each night, I ordered a lightly charred fish with a squeeze of lime and at least one ice-cold, perfect margarita. This was heaven—I was sure of it.

Soon, I learned that this was only one version of the many heavens the Caribbean has to offer. Off the top of my head (and I’m sure I’m forgetting a place or two), I’ve been to St. Barts, Saba, the Dominican Republic, Costa Rica, St. Kitts and Nevis, Trinidad and Tobago, Bequia and Mustique, Antigua, Barbados, Puerto Rico, Jamaica and Panama. Some, I’ve visited several times, and more often than not, aboard a boat.

I’ve been to St. Barts twice, once as a guest on a superyacht during the week between Christmas and New Year’s. The yacht was magnificent and the company was stellar, but the real fun of it was not being in the epicenter of the St. Barths holiday madness. If you like fine beachfront dining, cold and dry rosé, luxury boutique shopping and rubbing elbows with a who’s who of New York, then you’ll love St. Barts.

In Trinidad, I fell in love with the rich culture of Carnival: The highlight for me was Panorama, a multiday competition among steelpan orchestras that was sensationally exciting. People brought (and shared) picnics and stayed all day to cheer on their favorite bands. I found Trinidad fascinating. Oil reserves have driven the economy for many years, and it was refreshing to experience a Caribbean culture that’s not dependent on tourism. The food, with its mixture of African, Syrian, Indian and Chinese influences, was delicious, and the people were beautiful and friendly.

Extensive and well developed fringe reefs encircle most of the islands throughout the Caribbean. Many of these reefs can be found in shallow water, thus providing great opportunities for snorkeling and diving.

Extensive and well developed fringe reefs encircle most of the islands throughout the Caribbean. Many of these reefs can be found in shallow water, thus providing great opportunities for snorkeling and diving.

I almost bought a house on Nevis. I liked the mix of local and European residents, the lush scenery of the mountainous island that’s necklaced by stunning beaches, the soft breezes filled with the scent of Flamboyants, and the view to Montserrat in one direction and St. Kitts in the other. Getting to Nevis from the United States was a long and expensive trek, though, and I reluctantly let that particular dream go.

It was the first of my many trips to the British Virgin Islands that made me realize there was one perfect way to experience all of these Caribbean paradises—no choices required. Dazzled by the variety of places to explore in this island chain, and lulled by the steady breeze that seemed perfectly calibrated to temper the blazing sunshine, I saw immediately why so many sailors fall madly in love with the BVI. And line-of-sight navigation: What’s more enticing than being able to see the next adventure beckoning on the horizon?

In a way, the BVI is a microcosm of the greater Caribbean cruising experience. It’s the small lagoon in the big sea, and there’s plenty to like about that if you’re short on time or reluctant to make longer passages.

But, with all the comforts of home aboard and the security of a good engine, the Caribbean is a wonderland for adventurous trawler owners. Good fuel used to be a concern, but marine infrastructure and amenities have improved markedly in the past decade (despite the setbacks of Hurricane Irma and others). And, if you’re riding a solid, full-displacement hull with a single engine, a range of 2,000-plus nautical miles is common. That means you could fuel up in Miami and ride out hurricane season in the safety of Trinidad’s hurricane hole, Chaguaramas, on full tanks.

Of course, this is theoretical, for several reasons: You’d want the “plus” to cover your 10 percent reserve, and much depends on your cruising speed. Most of all, though, if you’re doing it the right way, you will have been seduced by at least a half dozen enchanting detours and will definitely need more fuel.

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The open secret to cruising the Caribbean joyously is this: Be flexible and avoid straight lines. By all means, make a plan. That’s never a bad idea: It educates you on what feels most important to see, how much time you’ll need for passages between islands, where you might put in to refuel or reprovision. I’ve always found that planning a trip doesn’t just prepare you; it adds to the anticipation. And if you have a good imagination (as I do), it’s almost like a bonus, virtual pretrip.

Usually, however, the Caribbean voyage you wind up making will have little in common with the one you imagined. Schedules here are merely suggestions and will be hijacked by everything from weather to new friendships to a favorite rum shack. Every island exerts its own brand of magic. What’s the hurry? you will think as you stroll the main street of Port Elizabeth on sleepy Bequia and turn to see your boat happily napping at its mooring. After all, there are fruit stands to visit and fresh fish to buy for lunch. And maybe afterward, a nap. Then we’ll dinghy down to De Reef for a rum punch and a swim. Let’s stay a while…

I know almost no one, for instance, who planned to spend as much time in the natural paradise of Dominica as they did. More than one friend has stopped to check out the place for a day and stayed a week, raving about its unexpected beauty. There are some lovely beaches, mostly black sand or rocky, but the real draw is the lush interior, which has waterfalls, nature trails and botanical gardens. Diving and snorkeling are fantastic here, too, so even if Dominica isn’t on your original route, stopping for a look may mean staying for a while.

Modern-day Caribbean islands draw on a wide range of influences—something that few other destinations can rival—so you may want to consider spending some time soaking in the local culture and history of the islands. From traditional music to classic cuisine, every island has a story to tell.  

Modern-day Caribbean islands draw on a wide range of influences—something that few other destinations can rival—so you may want to consider spending some time soaking in the local culture and history of the islands. From traditional music to classic cuisine, every island has a story to tell.  

Island hopping is part of the great allure of the Caribbean, and jumping from landfall to landfall makes for pleasant cruising. It reduces the wear and tear on guests and crew, makes it easier to provision, and eases the timing of passages for the best weather windows.

Most of all, though, the Caribbean relaxes a person like nowhere else. It’s awfully hard to worry about what’s happening at the office, or whether your investment portfolio has inched up or down, when you’re sitting on deck with a good book, a cold beverage and a view of a pastel-painted town, studded with palm trees and a welcome mat of soft, white sand.

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