Ocho Rios

The hospitality offered by “Scotchie’s” close-knit team of five—cook, butler, waiter, housekeeper, and gardener—is unmatched in Ocho Rios. Head chef Cherry consults with guests daily to craft seasonal menus that take into consideration dietary intolerances and food sensitivities. Rooms in this villa are impeccable, with high-quality linens and beautiful details, but the best feature of this five-bedroom house is its location. It’s right on the edge of a cliff, hovering above the White River Fish Sanctuary coral reef. Wake up early—sunrise over the Caribbean Sea from your bedroom window should help—and start the day with kayaking, paddleboarding, or snorkeling (all your gear is provided).

The resort is known for having the same feel now as it did when it opened (when Sir Winston Churchill used to come here to paint). Colonial-style cottages offset the tropical beachside setting that has a bit of a retro Jamaican feel—and there's croquet on the lawn. Blessedly, there are no TVs to be found. The rooms are as on the beach as it gets (open the door and step in sand) and they are happy to bring you breakfast on your veranda if you don’t feel like making it over to the palm-covered dining room.