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.

Yes, getting there is a bit of a project. But vacationers have been braving the ferry for years, and this tiny island off Cape Cod remains one of the most popular and picturesque destinations in New England. Among the island's towns, you're sure to find the Vineyard that's right for you. With stately Greek revival houses dating back to the whaling era of the early 19th century, Edgartown is a seaside village of boutique shopping and pristine harbour views. For more of a "beach town" feel, Oak Bluffs has the Flying Horses carousel, an arcade and an easy walk to the beach, plus the history and charm of the "gingerbread" houses in the Methodist campgrounds. Vineyard Haven offers visitors a blend of both. For a real retreat, Chilmark/Aquinnah is the place to get away from it all. In the off-season, the island is quieter and far less crowded, but the shore is always beautiful. Whenever you visit, leave your car behind! Cabs are plentiful and greet the incoming ferries to help you reach your destination. Most visitors prefer to explore the island on a bicycle, scooter or tourist-friendly public buses.

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.

Providence seamlessly blends the old and the new with historic attractions, museums and theatres situated alongside more recent additions like the scenic RiverWalk, outdoor skating centre, downtown mall, convention centre, hotels and acclaimed restaurants. Wander back in time while strolling down historic Benefit Street or explore Roger Williams Park Zoo with the kids. Tantalize your taste buds on Federal Hill or tour the city from a unique perspective on an authentic Venetian gondola.

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.

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.

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 won't lie: Niagara Falls is uber-touristy. There are wax museums and a Ripley's Believe It or Not Museum, and if it's a fast-food chain, you can probably find it here. But even the most jaded hipster shouldn't pass up a chance to visit this town, because the Falls themselves are spectacular.

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.

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.