Key West, at the southernmost tip of the US, is part party town, part tropical beauty, part artsy hideaway. The 4-by-1¼-mile speck of land jutting into the ocean—next stop, Cuba—has long been a hotbed of reinvention, a place to recharge, rethink, and reset. (Here’s looking at you, Ernest Hemingway and Tennessee Williams.) Several new boutique hotels have opened in recent years, bringing a welcome change from the island’s formerly fusty offerings. Among them is the Perry Hotel (7001 Shrimp Rd.; 305-296-1717), which has an industrial-chic design and a posh pool deck overlooking the marina. Cheap bikes, carts, and scooters throughout Key West mean you can explore the restaurants and famed bars without a car or a care. Because no visit is complete unless it includes time on the water, plan on a sunset cruise with craft cocktails aboard a historic Appledore schooner (205 Elizabeth St.; 305-704-8624).
Best of Jamaica
Jamaica really is the laid-back island that Bob Marley sang about, but its greatest pleasures are all too often hidden from visitors. Knowing where to stay is every-thing. For grown-up glam, book one of the new Caribbean-fronted luxury cottages at Jamaica Inn (Ocho Rios; 855-441-2044), a genteel retreat that has attracted movie stars since the 1950s. For family fun without the crowds, head to Half Moon (Rose Hall, Montego Bay; 800-626-0592), with horseback riding on the beach and spa treatments in bungalows overlooking the ocean. Another family favorite, Round Hill (Montego Bay; 800-972-2159), has rooms designed by Ralph Lauren, who owns a home on the lush property. All of these resorts can help you dig deeper into local culture by arranging tours of such attractions as coffee-rich mountain plantations, coral reefs, and famous film sites, including the locale for the James Bond movie Dr. No.
This article appears in the January 2019 issue of Washingtonian.