Antigua
SAILING IN THE CARIBBEAN? It's tough to narrow down to just one island, we know, but if there's a single place that balances both the sport and its well-lubricated after-hours lifestyle, it's 108-square-mile Antigua. The island has become the quintessential yachtie hot spot and, from late April to early May, hosts more than 1,500 sailors during Stanford Antigua Sailing Week, the Caribbean's second-largest regatta. More than 200 boats race in eight different classes, with participants ranging from landlubbers on chartered sloops to America's Cup winners crewing billion-dollar boats. And when the sails drop, the long pours begin. The island's own Antigua Distillery churns out award-winning rums (pick up a bottle of the English Harbour five-year-old). In Falmouth Harbour, where many of Sailing Week's festivities take place, work your way from the Last Lemming to the Mad Mongoose and then on to Skullduggery, where it's required that you have at least one espresso martini before hitting up the bars in English Harbour.

PLAYTIME: A slew of private charter companies like Horizon Yacht Charters, whose founder, Andrew Thompson, often races in Sailing Week, operate out of Antigua (a full list is available at sailingweek.com/imc/charters). Qualified captains can take off on their own, or you can always hire a skipper.

ISLAND LIVING: If you don't feel like sleeping where you sail, grab a room at the newly opened—and swanky—Antigua Yacht Club Marina and Resort, in Falmouth Harbour. They'll even dock your boat for a daily rate. Doubles from $277; aycmarina.com