The dilemma: Should you go surfing this winter, or sailing? Most warm-water spots force you to choose one or the other, but in the Virgin Islands you better bring your surfboard on your charter. From Road Town, Tortola, set sail for Cane Garden Bay, on the island's north side. After securing a mooring, hop in the dinghy to Apple Bay for some serene right- and left-hand barrels, or simply paddle out to the Cane Garden's peeling right-hander. From there sail to the north side of St. Thomas and surf Hull Bay.
More information: Skip crowded January and February (for chartering information see moorings.com).