St. John’s vibrant main town and port, Cruz Bay is home to most of the 28-square-mile island’s restaurants, bars, stores and dive centers. Two-thirds of affluent St. John is a national park, and many safari buses and jeeps set out from Cruz Bay. Don’t miss local art and history at Elaine Ione Sprauve Museum or the pristine sand of Hawksnest Bay, popular with snorkelers due to its nearby reef. There is no airport; ferries connect the town of 2750 with other U.S. and British Virgin Islands.

The former haunt of pirates, the Dutch and the English and Tortola's main town, Road Town is within reach of secluded beaches and hidden coves. The island displays the same leisurely pace as other British Virgin Islands, with festivals and regattas across the calendar. Helicopter and sea charters and diving are popular activities. On land, the ruins of Fort Burt and the still functioning Callwood Rum Distillery provide fun daytrips. Catch a cab between sights or rent a car to get out of town.

Who cares about a little fog (okay, a lot of fog) when there’s so much to do in San Francisco? By day, explore Fisherman’s Wharf and the Aquarium of the Bay, ride a cable car, and stroll around the Presidio; by night, have a fabulous dinner (at a Michelin-starred restaurant or a tiny place in Chinatown), then hit some of the best clubs on the West Coast.