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.)

It's still one of the most British cities in North America, but there's more to Victoria than tearooms, antique shops and galleries (though there are plenty of those). Driven by the younger generation, the city has sprouted a collection of cool shops, authentic coffee bars and unique restaurants. It also has more cycling routes than any other Canadian city, providing a great way to explore the picturesque location (and avoid an afternoon of antique shopping).

San Diego embodies laid-back California culture, complete with a Boardwalk, surfing communities, and outstanding Mexican food. Breathe in the fresh ocean air at Sunset Cliffs Natural Park, then gobble down a fresh fish taco at a La Jolla seafood joint. The naval aircrafts at the USS Midway Museum will have you standing at attention. A free Sunday concert at the Spreckels Organ Pavilion is the perfect way to unwind after a Saturday night bar-hop in the thumping Gaslamp Quarter.

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.

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.

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.

Virginia Beach has all the elements of a classic seaside resort: gorgeous beaches, a lively boardwalk, plenty of restaurants and nightspots, and amusement rides sure to appeal to kids. Sports enthusiasts will find celebrated golf courses in Virginia Beach and the surrounding area, as well as sea kayaking and miles of hiking trails. Many believe Virginia Beach is at its best in the off-season, when the town is less crowded but the weather is still mild.

From the Magic Kingdom to magical spa treatments, Orlando sparkles with the promise of adventure. Spend a day exploring the world-famous Disney theme parks or screaming your head off on a Universal Studios roller coaster. For a less adrenaline-pumping afternoon, enjoy the quiet natural beauty of the Harry P. Leu Gardens or enjoy a seaweed scrub at a luxury day spa. Savor fresh and local ingredients at one of Orlando’s James Beard-nominated restaurants.

This canal-laced city is a far cry from its rowdy, party image of the past. Today, following renovation and renewal, upmarket stores and restaurants have replaced fast-food stands and T-shirt shops. But the city's biggest draws are its stretch of gorgeous beaches, great swimming, nearly year-round sunshine and close-to-ideal climate. For great shopping, dining and nightlife, you can't go wrong at Las Olas Riverfront, a waterfront entertainment centre with top-notch clothing and jewellery shops, bars and free entertainment. The city has a host of family-friendly options, such as Everglades Holiday Park and the Museum of Discovery and Science. With the network of canals and waterways, boats are part of the Lauderdale lifestyle, and tourists can get in on the act by hiring a boat or hailing a water taxi. There's a lot to do here, but make sure and spend some quiet time just soaking up the sun or strolling along the beach at dusk.