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Or three. Settled in the late 1600s and named for England’s Prince James, this Rhode Island town comprises the 9-by-1-mile Conanicut Island and the much smaller Dutch and Gould Islands, the last having served as a military fort and a torpedo station during both World Wars. Today, Jamestown is a great place to watch the seasonal parade of boats heading to and from Newport, as well as the numerous local regattas—all while avoiding the general hubbub of that busy harbor to the east. “If you’re passing through on a boat, Jamestown is a little easier to deal with than Newport,”...

Brant Point Light.Nantucket Harbor has come a long way since its days as a whaling hub. Today, the well-protected port welcomes mariners of a very different sort, who come to stroll the narrow cobblestone streets, dine in five-star restaurants, browse the boutiques and art galleries or relax on beautiful beaches. And it’s surprisingly accessible, even for daytrippers, lying just 26 miles south of Hyannis. If approaching from the west, use the Cross Rip Channel, between Cross Rip Shoal and Horseshoe Shoal. Keep Tuckernuck Shoal to starboard as you plot a course for the red-white “NB” buoy. The twin jetties flanking the...