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.

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.

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.

Corner Brook, a small but bustling city, is on Newfoundland’s west coast. Captain Cook initially mapped this area, known as the Bay of Islands, in 1767, and like many other Newfoundland settlements, Corner Brook started out as a fishing village. Later, one of the largest pulp and paper mills in the world was built here. In the city’s downtown core, West Street and Broadway are the center of action, thanks to numerous pubs, shops and restaurants. The local university has renowned fine-arts and drama programs, so you’re never too far from entertainment. Corner Brook also has an impressive amount of green space—you’re always within walking distance of a park or trail. Nearby Humber Valley and the Marble Mountain offer some of the best skiing in Atlantic Canada, a big enticement for outdoor-adventure junkies. Even if you’d prefer to just take in the scenery, the rolling green mountains and the views overlooking the bay are worth the trip.

On a Caribbean Cruise, the capital island of the U.S. Virgin Island is often the first stop for travelers. Its easy access, use of American currency and cultural cues, as well as its reputation for safety, make St. Thomas the easy first choice. But just because it appeals to the comfortable side of travel doesn’t mean that St. Thomas is basic. Just the opposite—the 80-square-kilometer (31-square-mile) island is full of superlatives. It’s home to some of the Caribbean’s highest viewpoints, spectacularly positioned among verdant tropical foliage. It offers some of the best snorkeling around. And the island has got the hands-down coolest attraction in the region—an ice museum. Cruise to St. Thomas and surround yourself with pristine beaches, excellent shopping and dining. Charlotte Amalie, the main town in St. Thomas, buzzes with activity. It’s one of the busiest cruise ports in the Caribbean. Founded in 1666 and renamed in 1691 to honor the Danish queen, Charlotte Amalie contains excellent of all Danish-colonial architecture. In fact, a number of sites in Charlotte Amalie are listed on the National Register of Historic Places. Seeking a relaxing vacation for a fun adventure? Explore an array of activities like a guided Sea Trek Helmet Drive at Coral World Ocean Park, or go snorkeling and after relax under the palms while sipping on a refreshing beverage. Discover these activities ranging from scuba diving to food tours on a cruise to St. Thomas

Gorgeous, green and Gallic, this charming village is your gateway to some of the most stunning scenery in North America: majestic fjords, dramatic rocky capes and picturesque hamlets are all here. So are artisans of every ilk, from glassblowers to angora goat farmers. Sample shore excursions: Saguenay Village Highlights; Saguenay National Park by Zodiac (or Seaplane); The Craftsman Road.

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.

Montréal, Canada is a city of contrasts, one that defies a simple description or a catchy tagline. It sits on the New World’s St. Lawrence River, yet it has an undeniable Old-World French flair. It is a historic city, founded in 1642, and the streets of Old Montréal are lined with sights that range from a 17th-century seminary to grand commercial buildings erected in the 19th century. But Montréal is also home to contemporary architectural masterpieces—most notably those erected for Expo 67, including Buckminster Fuller’s Biosphere. Montréal is at once the cultural capital of the Québecois and a decidedly global and cosmopolitan city, attracting migrants from around the world. The walls of its galleries and museums showcase leading artists from the province and the rest of Canada, while the city hosts festivals that feature the best international films, musicians and performers. Many of its restaurants serve traditional specialties—poutine, bagels and smoked meats; others are helmed by some of the continent’s most innovative chefs. Montréal is a vibrant urban center, with buzzing streets and attractions, yet crowned by peaceful, leafy Mount Royal Park, designed by Frederick Law Olmsted (also responsible for New York’s Central Park). Whichever of the city’s many aspects appeals to you most, you are sure to be charmed by this unique city and find many things to do in Montréal.