Where to stay: In Kingston, the Courtleigh, Knutsford, and Pegasus hotels are popular with business and urban travelers. Hostels offer rates as low as $14/nt, and airbnb options are available as well. If you overnight in town, stay in New Kingston -- it's nicer and closer to the nightlife than the downtown area, which shuts down after dark.
Outside the city, there're plenty of stylish (and historic) resorts from which to choose, including the recently renovated Goldeneye, the one-time island residence of famous 007 author (and British spy) Ian Flemming where many James Bond novels were penned. Strawberry Hill in the Blue Mountains is your move for a romantic getaway, while -- back along the coast -- the elegantly rustic Tensing Pen and Rockhouse in Negril both redefine sexy. Finally, if you want to feel like a welcomed local from the moment you arrive, then Jake’s in Treasure Beach is your play.