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.

Sydney is the largest city on Cape Breton Island, which is linked by causeway to the rest of Nova Scotia. Sydney’s attractions start at the harbor, where visitors can shop for locally made crafts and see the world’s largest fiddle, which towers beside the port’s cruise pavilion. Some of the city’s historic houses and churches date back to the 1700s and 1800s and are open for tours. Restaurants often provide live music (expect fiddles and sea chanteys) along with meals of seafood fresh-caught in nearby waters. Sydney’s galleries give visitors a chance to meet local artists and purchase their work. Cape Breton’s natural wonders include the spectacular scenic drive known as the Cabot Trail. Hikers in Cape Breton Highlands National Park will find stunning vistas around every turn, while a boat ride on massive Bras d’Or Lake, which is ringed by wild hills, offers a different perspective on the province. Explore the region’s past with a visit to the Fortress of Louisbourg National Historic Site, and learn about the area’s First Nations communities at Membertou Heritage Park. If you decide to go deep underground at the Cape Breton Miners Museum, your tour guide is likely to be a man who toiled for years in the island’s coal mines and has many stories to tell. Another must-see: the Alexander Graham Bell National Historic Site, where the famous inventor made his summer home.

Saint John, on the southern coast of New Brunswick, is Canada’s oldest incorporated city as well as the only city on the Bay of Fundy.

Give your stroll through uptown Saint John a little focus by taking the self-guided Loyalist Trail walking tour, which visits historic attractions like the 1784 Burial Grounds, the 1876 Old City Market, a general store and the Jewish Historical Museum. The New Brunswick Museum, also along the Loyalist Trail, tells the story of the town and exhibits cover some of its natural history, too, with an 80,000-year-old mastodon skeleton. The Martello Tower has been part of Saint John’s identity since it was erected for the War of 1812; it was even used to house prisoners during World War I.

The most exciting part of your trip to Saint John may be your chance to view the point at which the Bay of Fundy and the Saint John River collide: the Reversing Falls Rapids. If simply observing the churning waves and whirlpool is not enough, ride a zip line over the waters for added thrills.

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.