New England’s largest city, Boston, Massachusetts, is home to historic sights and modern neighborhoods; stores and restaurants with old-time character; and gracious green spaces as well as a beautiful waterfront. Legendary figures of the American Revolution come alive at buildings and attractions along Boston’s Freedom Trail, including the Paul Revere House and Old South Meeting House, and in Lexington and Concord just outside Boston. Pay homage to great U.S. presidents at the John F. Kennedy Presidential Library and Museum and in the town of Quincy, birthplace of Presidents John Adams and John Quincy Adams.

Each of Boston’s neighborhoods has its own personality and things to do, whether you’re enjoying the food of the North End’s Little Italy, admiring the beautiful 19th-century architecture of Beacon Hill or watching the street performers in Cambridge’s Harvard Square. The waterfront offers harbor views, while boat tours allow you to take in the city skyline while sightseeing. In every neighborhood, shopping and dining reveal Boston’s true eclectic self, from casual to high-end, but always interesting.

Finally, Boston is a city of green spaces where you can relax and enjoy the outdoors. The Emerald Necklace, designed by Frederick Law Olmsted, is a 445-hectare (1,100-acre) chain of nine linked parks, including the lovely Boston Common and Public Garden.

Squint your eyes and admit it: Doesn’t that skinny, bearded hipster walking down the cobbled street look a lot like a 19th-century sea captain heading to the wharf to check his ship? Modern Portland, first settled in 1633, carries the marks of both subsets of Mainers. The restored brick buildings and warehouses of the Old Port and the fine upright houses of prosperous captains, merchants and shipbuilders make the city’s past a living part of its present. And the waterfront is a going concern, not a museum: Fishing boats chug into and out of their berths, buoys clang, harbor seals bark. Those shop windows aren’t displaying hardtack, rope or hand salve, though. Juice joints, art galleries, bookstores (and comic-book stores!), worshipful temples to coffee, locavore bistros with national press, bespoke menswear designers and gelato shops all jostle for attention. Don’t limit your visit to the Old Port, though. Wander through the terrific art museum or take a tour of one of the city’s historic homes. Jump on a ferry or whale-watching boat and get out into the busy harbor. Head to the coast—craggy, windswept, dramatic—a glorious and undeniably New England panorama. Get out and take it all in. Welcome to Vacationland.

Located on a rocky inlet on the Atlantic Ocean, Halifax—Nova Scotia’s provincial capital—is defined by its maritime geography. It’s a spirited mix of world-class history and nautical-themed museums alongside bunkers and fortresses that guarded the harbor, plus striking public art and sights, funky shops and excellent pubs serving up folk music (and good pints).

Explore the Halifax waterfront where steamships once anchored to drop off arriving immigrants at Pier 21. Savor the low-key but classy culinary scene for fresh seafood and Nova Scotia specialties—the city has both street vendors and casual joints catering to university students and upscale eateries with elegant settings. Along Nova Scotia’s southern shores, the city is surrounded by lush greenery and charming villages that are worth the trip from downtown proper. Snap photos of attractions in the charming fishing village, Peggy’s Cove, with its picturesque lighthouse on a rocky outcropping. Or wander the streets of Lunenburg, whose colorful Old Town is designated a UNESCO World Heritage Site. You can also soak in the charms and sights of Mahone Bay, home to artists’ studios and a trio of steepled churches.

Charlottetown is the capital of Canada’s smallest province, Prince Edward Island, as well as its largest city, though it has fewer than 35,000 residents. Despite its modest size, the city has an impressive number of Victorian houses and buildings and great parks waiting to be explored. For Canadians, it is perhaps most famous as the Birthplace of Confederation. It was here, mostly at Province House, that an 1864 conference led to the creation of the Dominion of Canada.

Prince Edward Island is linked to New Brunswick on the mainland of Canada by the 13-kilometer (eight-mile) Confederation Bridge that soars over the Northumberland Strait. A remarkable feat of engineering, the bridge opened in 1997 and is the longest in the world over icy waters.

Sites within downtown Charlottetown include the lovely Victoria Row, which becomes a pedestrian mall each summer, and other historic buildings, some of which are now museums. Nearby Prince Edward Island National Park is home to white-sand beaches and hiking and biking trails—plus fans can see the house and farm that inspired the beloved book Anne of Green Gables. During your visit, you can also learn about the daily lives, past and present, of residents on lighthouse and boat tours.

Few places in North America are as steeped in history as Québec City, Canada. Older than Jamestown and founded before the Pilgrims landed at Plymouth Rock, it is the only city north of Mexico whose original fortifications remain intact. The Québec City historic district, a UNESCO World Heritage Site, is still home to religious orders and hospitals that date back to the 17th century. Its Place-Royale would look familiar to the explorer Samuel de Champlain, even with its modern attractions of gift shops and cafés. On the Plains of Abraham, you can walk the battlefield where, in 1759, the French forces under General Montcalm were decisively trounced by the British, led by General Wolfe.

The British took control of all of New France within a year of that 1759 battle, but even so French culture still lives on here in Québec City. More than 95 percent of Québec City’s population speaks French as its first language, though it’s easy to sightsee and navigate the city in English. As you tour the museums and historic sights of Québec City that celebrate Québecois history and dine at restaurants that serve its distinctive cuisine, you’ll discover a remarkable culture that has survived and thrived into the 21st century.