When I told my parents I was going to Jamaica—with two female friends, on a road tip—the parental anxiety was palpable from across the Atlantic. (Our route: a loop around the lush eastern side of the island, starting and ending in Kingston and stopping in Treasure Beach, Oracabessa, and Port Antonio along the way.) And they did have some valid concerns: Though much of the violence there is confined to easily avoided areas of major cities, Jamaica has a disproportionately high crime rate for an island its size. 

The roads can be difficult to manage. And we had chosen to risk going during the tail end of hurricane season. But, thanks to plenty of advice from friends on the island, careful planning, and probably some good luck (at least with the weather), we were fine. 

In fact, it was one of the best trips any of us had ever taken—and knowing your parents disapprove rarely makes something less fun. Here's what else I learned.

1. If you do rent a car, be prepared.

The roads are potholed, speed limits are largely ignored by other drivers, and, if you're coming from the U.S., you'll be driving on the "wrong" side of the road. Upgrading to a 4x4 is more than worth it. Drive with confidence (bordering on aggression). And before you leave the car rental facility (we chose Avis), make sure to double-check you have a functional spare tire—even some of the so-called highways are extremely potholed and punctures are common.

2. Plan your route carefully.

Planning a route in Jamaica is not a question of plugging point A and point B into GoogleMaps as it often is at home. Sometimes what looks like a major road on a map is actually just a dirt track, and sometimes, thanks to hurricane damage, it doesn't exist at all. Talk to people on the island (the staff at your hotel are a great place to start) before plotting out your journey. But a general rule of thumb is that taking a larger "A" road will always be quicker than a series of smaller "B" roads—even if this means adding miles to your drive.

3. Go in the off season.

Hurricane season in Jamaica runs from July through November, and while the risk of visiting the island during these months is clear, the benefits are equally hard to ignore: hotel rates drop by anywhere from 20 to 60 percent, tour and activity rates are slashed, and in many places you might be the only person on the beach.

4. Mix up your accommodation. 

Jamaica is home to some of the most iconic (and sometimes therefore expensive) resorts in the Caribbean— Round Hill, GoldenEye—but it also has some of the best budget-friendly options. Jake's, the legendary hippie hotel in Treasure Beach, offers double rooms starting at $95 in low season, for example.

Check out more tips for traveling in Jamaica.

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