Jamaica 101

As anyone who goes knows, Jamaica has soul. Amid a sea of islands that tourism has changed and sometimes overtaken, Jamaica remains distinctly its own place, its soul potently intact. It came at an extraordinary price: from, largely, the suffering of a century’s worth of slaves, imported starting in the 1600s, and the frustrating history that followed. Eventually the populace gained its freedom, with abolition in 1838, but it took another century and then some for the country to win control of its own destiny, when Britain departed, in 1962.

Fifty years later, visitors can certainly go to a resort here for a quick beach getaway, never leave the property for three or four days, and have a great break. With its abundance of beachfront hotels and direct flights, Jamaica is ideal for a “flop and drop” vacation, and in the main it will be easier and less expensive than elsewhere in the Caribbean.

But even as you stretch on your chaise, a Red Stripe beer at your lips and a pile of plantain chips at your fingertips, you’ll sense—you’ll know—you’re somewhere…different. The character forged by the nation’s long and rough-edged coming of age created a people and place with their own outlook. Not for nothing does reggae celebrate— even more than acceptance and understanding—fortitude and strength. Unlike neighboring islands that developed mostly because of tourism, Jamaica is a country where tourism coexists with many such forces, some good, some not. A place apart, deep and multilayered, it rewards those willing to confront its complexities and reflect on what they see. Those willing to dance, or at least think, to Jamaica’s beat.

Or you can just stay right on your chaise, and have another Red Stripe or rum. No one who’s been to Jamaica could argue with that, either.

When to Go

There’s definitely no good reason not to go in peak season if you can, January through March. But don’t discount other seasons entirely; even in the rainiest months (May, October), downpours can be brief, and it’s the mountains, not the coasts, that tend to get the heaviest accumulation. Properties may use the lull caused by hurricane season to shut down and spruce up, but otherwise Jamaica is open all year, and temperature-wise consistently pleasant. The daytime temp varies little and even in July averages in the 80s.

Getting There

Fly into Montego Bay, at the northwest corner of the island. From there your hotel or villa is anywhere from 15 minutes to 2 hours away, unless you’ve chosen to go somewhere more adventurous, like Port Antonio, almost at the opposite end of the island and roughly four hours away. Jamaica is a direct flight from New York and Boston.

Getting Around

You don’t need a car of your own. You’re probably not going far once you reach your hotel, although the roads are now good and so are most drivers, if a bit daring in the way they hopscotch around other vehicles when passing. If you do decide to make a day trip to the Blue Mountains, or you just want to go elsewhere for golf or dinner, taxis and hired cars are definitely the way to get there.

Indagare Tips

In one sense, it’s not so hard to pick a great place for your Jamaican vacation. There’s a huge gap between the handful of top-tier properties and all the rest (the mass-market Caribbean package trip was practically invented here), and you already know on which side of the divide you want to be. But because the choices within the upper rank are quite different in personality, and because you’ll probably be spending most, if not all, of your time on the grounds of your hotel (breakfast, lunch and dinner, for several days), you’ll want to match your family’s expectations with a property that can deliver on them. Don’t worry about the distance from the airport, or getting a great deal, as much as the bigger picture of suiting your style. Let that be your guide first and foremost.