This pleasant, walkable town right at the elbow of Cape Cod is a classic New England vacation spot. Bringing kids? Check out calm beaches like Cockle Cove Beach and Harding’s Beach. If you’re looking for stunning scenery, however, try Chatham Lighthouse Beach. Its tides can be strong (heed the posted warnings), but it’s one of the most beautiful beaches on the Cape.

Windswept beaches, sand dunes, blinking lighthouses and a charming pace of life await on this 50-square mile island. The world's former top whaling port is now designated a National Historic District. Leave the car and take the shuttle or bike around. Seaside cottages, old whaling captains' mansions and historic harbours contain quaint inns, boutique stores, chowder shacks and upscale dining delights. Swim, surf or load up the tackle for Nantucket's excellent striper, bluefish and bonito fishing.

It's no wonder that the Pilgrims fell in love with America when they landed at gorgeous Plymouth, set in the calm waters of Plymouth Harbor along Cape Cod Bay. It was here that the first English colonists made war and then peace with the Natives, celebrating their newfound cooperation with the first Thanksgiving dinner. Visit the landmarks that honor this piece of American history, from Plymouth Rock to Mayflower II to Burial Hill. Or just enjoy the sandy beaches and calm sea breeze.

Middletown, Rhode Island, is home to miles of wide sandy beaches, thousands of acres of unspoiled nature preserves, historic attractions, outdoor recreation and many restaurants. Bordering the popular resort city of Newport, this diverse coastal community is where you’ll find the Norman Bird Sanctuary, which encompasses more than 325 acres of diverse habitats and seven miles of marked trails, as well as the Sachuest Point National Wildlife Refuge, which offers a 2.5-mile trail with panoramic ocean views.

You've got to walk the Freedom Trail the first time you visit Boston. That's just a given. Make sure you step off the line on the pavement, though, and explore some of Boston's fine museums (try the Gardner—art masterpieces displayed in their collector's mansion) and old neighbourhoods (like the North End, where you can get the best cannoli this side of Italy). You can't claim to have experienced real Boston culture, though, unless you've watched a Red Sox game from the bleachers.

Home to two of America's most prestigious universities, Cambridge exudes a certain intellectual quirkiness. A mix of historical haunts, student hang-outs, alternative art and culture venues, vintage clothing shops, bookstores and ethnic restaurants, the city is, well, really cool. Although it is located just across the Charles River from Boston, Cambridge has a distinct vibe that is noticeable immediately. Start at Harvard Square, a hub of activity and mishmash of trendy stores, outdoor cafes and colorful local characters. Pick up a walking tour map at the visitors information booth in the centre of the Square. The route will take you past many important landmarks including the Mount Auburn Cemetery, Tory Row and the Longfellow National Historic Site. Harvard University offers student-led tours through the illustrious buildings and monuments of its sprawling campus. Art and architecture buffs should meander around the M.I.T campus, which includes outdoor sculptures by masters such as Picasso and 20th-century buildings designed by modern greats like Eero Saarinen and I. M. Pei. Along the way, browse through bookstores, stop to watch street performers and grab a coffee at an outdoor café to take in all this captivating city has to offer.

Best known for the witch trials that took place in 1692, Salem is sure to bewitch you with its seaside charm, its maritime history and spellbinding beauty. Follow the Red Line along the sidewalks to navigate your journey through historic sites, including the Witch Trial Memorial, the Old Burying Point Cemetery and more. Discover serenity by the sea on the beaches of Salem Willows. The Bewitched statue, the Witch Museum and the Witch Dungeon conjure up diverse takes on witchery through history.

With its sandy North Shore beaches, rocky outcrops, green parks, hemlock woods and wild estuaries full of shorebirds, it is no wonder that Gloucester has attracted such a rich and diverse artists' community. Fitz Hugh Lane, Winslow Homer and John Sloan are just some of the artists who have taken inspiration from Gloucester's beautiful surrounds. Still boasting dozens of galleries and boutiques, as well as museums, theaters and an artists' colony, the city's art scene clearly continues to thrive.

The first time you go to New York, go ahead and be a sight-seer—everyone should visit the Statue of Liberty, the Met, Times Square, etc. But on a return trip, pick a neighbourhood and go deep. You’ll find hole-in-the-wall bars, great delis, quirky shops… exploring the non-touristy side of New York is an incredibly rewarding experience for a traveller.

Montreal, c’est si bon! This French-speaking city is considered the cultural capital of Canada, and is a cosmopolitan celebration of Québécois style. A horse-drawn carriage ride around the cobblestone streets and grand buildings of Vieux-Montréal will give you a taste of European flavour. The Basilique Notre-Dame is a confection of stained glass, and the Plateau Mont-Royal district will delight you with its quaint boutiques and cafés. Dig in to a massive plate of poutine to fuel up for a tour of the epic Olympic Park.

Ottawa is a compact, clean, cleverly planned centre of culture and politics. And it's an ideal choice for a weekend getaway. Start downtown at the architecturally stunning National Gallery of Canada, and don't miss the Canadian Nature Museum and the National Aviation Museum. Rideau Canal offers boating in the summer and ice-skating in the winter. Gatineau Park attracts cyclists and walkers, while Byward Market blends old and new Ottawa.

We've heard Toronto described as "New York City run by the Swiss," and it's true—you can find world-class theatre, shopping and restaurants here, but the sidewalks are clean and the people are friendly. The best place to start is literally at the top—the CN Tower, the tallest freestanding structure in the Western Hemisphere.

A cosmopolitan city known as the "cultural cradle of Canada," Winnipeg is family friendly with plenty of charm. It boasts a dazzling arts, theatre and indie music scene, as well as lip-smacking dining options to tantalize every taste bud. Experience nine acres of shopping and interactive fun at the Forks Market or explore Winnipeg’s diverse neighborhoods like the historic French Quarter and Exchange District or the boho chic Osborne Village.

Although situated on a flat plain with few indigenous trees, Regina boasts some of western Canada's most innovative urban landscaping, with plentiful green spaces, hiking and biking paths, playgrounds, oak-lined streets and parks throughout the city. The popular Wascana Lake plays host to summer boaters and winter skating. Regina is also home to numerous cultural and educational institutions, including museums, galleries, theaters and Canada's RCMP Training Academy Grounds.

Named for the sweet berry that grows wild in the region, Saskatoon boasts various cultural festivals, concerts and sporting events throughout the year. Explore the trails and beaches of Beaver Creek and Cranberry Flats, cross-country ski the Meewasin Valley Trail, check out the city's many galleries and museums, and shop for bargains at Midtown Plaza.

As North America’s northernmost large metropolis, Edmonton is a fascinating study in contrasts — a vibrant urban centre in the heart of the wilderness. It’s a city that’s never been afraid to do things a little differently, as visitors discover through close encounters with free-roaming bison, a shopping mall that spans more than 48 city blocks, and a dynamic arts and culture scene that embraces more than 40 annual festivals, including the continent’s biggest and wildest Fringe Theatre Festival.

What happens when a "gassy" Englishman rows into town feeling thirsty? A pub is born. And from that a city—in this case Vancouver. Though the pubs are plentiful, food and drink aren’t the only things to take in during your trip. In its 150 years, Vancouver has grown into a cosmopolitan city nestled in the great outdoors. Enjoy the snow-capped mountains, waterfront forests, cityside beaches, Olympic history and the world’s highest suspension bridge. Hipsters welcome. (Don’t worry, they don’t bite.)