There are many reasons to travel to the Caribbean: the crisp splash of crystalline waters, the warmth of afternoons spent beachside, and even the post-hike glimpse of forested cliffs atop volcanic islands. But no one who spends the time and money flying to these islands need lock themselves inside some carbon-copy all-inclusive without a sense of place. To help break out of the resort-industrial complex and offer some inspiration, our comprehensive guides, itineraries, and hacks will help you plan your next trip to the tropics—and fill it with sights and experiences you’ll remember for life.