British Virgin Islands
Price per night: From $225
Why you should go: This eco-resort, only accessible by private boat, has an extensive bar of rare rums.
While yacht-up resorts aren't exactly a rarity in the BVI, the king of the crop is at Cooper Island. By day, the bar overflows with folks in Vineyard Vines and Sperrys, taking their drinks to the in-water cocktail tables. The solar-powered resort is also home to one of the Caribbean's most extensive rum bars, where you'll find rare-production stuff in a space barely bigger than a utility closet near the main restaurant. The custom-roasted coffee is worth the ferry ride from Tortola, even if you're not staying at the resort. But if you are, the rooms are big, airy suites perched atop the hills behind the main house, each with balconies staring out onto the vast Caribbean.