Halifax, N.S., Canada
Anchored by history and propelled into the 21st century by its vibrant citizens, Halifax welcomes visitors with open arms. The harbor is one of the safest in North America. Tie up at Bishop’s Landing, which is close to everything — the Old Triangle Irish Alehouse feels like old Ireland; the Historic Properties section preserves the city’s 19th century character; the tour of Alexander Keith’s Brewery is delightful theater, and the beer is tasty. BRISTOL, RHODE ISLAND Bristol has been a mainstay of America’s maritime scene since 1878, when John Brown Herreshoff and his younger brother Nathanael started Herreshoff Manufacturing Co. and began building what would prove to be some of the fastest racing yachts on the water. Bristol continues to offer a bustling summer season for residents and tourists.
Clayton, New York
David Dodge wrote in to nominate Clayton, home of the Antique Boat Museum, and said, “The yachting/cruising possibilities to and from Clayton are endless. Within a few hours you could be in Lake Ontario with access to the New York State Canal System (Lake Champlain, Finger Lakes, Hudson River) at Oswego, New York. Or, on the Canadian side, to Kingston, Ontario, where the scenic Rideau Canal could take you to Ottawa.”

San Francisco, California
The next America’s Cup will be brought to you live from San Francisco and that’s probably all we need to say about why the City by the Bay is one of the 50 Best towns. Plenty of wind and current make the Bay Area delightfully challenging for mariners. Home of the prestigious St. Francis Yacht Club, the oldest yacht club west of the Mississippi, as well as dozens of other clubs and marinas, San Francisco loves its water, which, thanks to topography, remains the focal point of nearly every view from its vertical streets.
Gloucester, Massachusetts
Gloucester is best known as a fishing town, with a wonderful working waterfront, but it also has shipbuilding roots that date to 1713. If you’re in town and are looking for local color, head to the Crow’s Nest Bar.
Kingston, New York
Kingston, located on the Hudson River, was once a historically important shipping hub. Today, it has an active arts community and a better restaurant scene than most towns its size, thanks to graduates of the nearby Culinary Institute of America. Rob Kinnin also pointed out that “Kingston gets a very nice complement of yachts here as a stopover going to/ from New York City to the canal system.”
Marblehead, Massachusetts
Carol Kent nominated Marblehead and noted a couple of things she likes about it. “Few marinas make this a good-looking and safe harbor for the working fisherman and lobsterman on the mainland; a causeway connects the land to ‘the Neck,’ home of summer people [and] now year-round folks.” It’s an easy commute to Boston for the boater still anchored to a desk.
Monterey, California
Monterey is located within the Monterey Bay National Marine Sanctuary — 276 miles of federally protected coastline that provides great wildlife watching. Schedule your trip during one of the city’s two main music festivals: the Monterey Jazz Festival or the Monterey Pop Festival, whose inaugural show in 1967 drew the likes of The Who, Jimi Hendrix and Janis Joplin.



