The Continental U.S. runs out of land at Key West, which is why it's always been a dropout's paradise, attracting artists and drinkers such as Tennessee Williams and Ernest Hemingway. The place I'd most like to drop out to, chilled beverage of choice in hand, is Sunset Key, a small and exclusive island of Key West, which features a dazzling array of elegant, pastel-colored cottages, its own private beach and resort precinct, and the lovely gourmet restaurant and bar, Latitudes.
This tiny island is reached by taking a launch from the wharf outside of its sister property, the Westin Key West Resort & Marina. In a few minutes you will indeed arrive in paradise, which is actually a part of the Luxury Collection Resort; If you're very lucky you will have booked one of the Sunset Key cottages and be about to embark on the kind of retreat that Oprah enjoys. If that's beyond your budget this time, maybe you'll be lucky enough to snag an outdoor table at Latitudes. There, you'll be torn between gazing at the gorgeous cuisine on your plate, or at the stunning, technicolor sunset right in front of you.