Just west of London, Reading offers redbrick Victorian buildings, medieval ruins, a thriving university, and pretty waterside walks along the Thames River. Its student community and annual rock-music blowout—the Reading Festival—add an offbeat edge.

If you saw Chevy Chasy's masterpiece European Holiday, you'll recognise Stonehenge's massive formation. (As a citizen of the world, you should recognise Stonehenge anyway.) The prehistoric stone circle is eight miles from Salisbury, and its visitors provide a boost to the local economy. With a history dating back over 5,000 years, there is no shortage of significant places to visit in and around Salisbury. On the "must see" list are Salisbury Cathedral, Longleat and Stourhead gardens (and Stonehenge, of course).

Presided over by its cathedral, where Jane Austen is buried, and medieval castle, home to King Arthur’s Round Table; Winchester wears its history on its sleeve. A maze of cobbled lanes and half-timbered buildings harbour old English pubs, traditional cafés, lively markets, and artisan shops.

From Shoreditch’s swaggering style to Camden’s punky vibe and chic Portobello Road, London is many worlds in one. The city’s energy means that no two days are the same. Explore royal or historic sites, tick off landmarks from your bucket list, eat and drink in exclusive Michelin-starred restaurants, enjoy a pint in a traditional pub, or get lost down winding cobbled streets and see what you stumble across – when it comes to London, the possibilities are endless.

Visitors flock to Poole for its sandy beaches—like the prestigious Sandbanks—and for boat trips in one of Europe’s largest natural harbours. A buzzing quayside, trendy restaurants, and sundowner bars make Poole one of southern England’s most popular seaside spots.

Home to a colorful array of culture and cuisine, Leicester combines traditional English heritage with a diverse cultural scene. Famous for the National Space Centre, the city offers English staples such as pubs and parks, and is the final resting place of King Richard III.

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.

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.

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.

Among the best golf destinations in the world, Punta Cana is the very picture of leisure. Several of the courses have been designed by professional golfers, making for the perfect sort of kicked-back challenge that you want on a golfing vacation. The beaches here are simply perfect: calm, warm waters that gently lap at stretches of fine white sand. Thrill yourself with a zip-line adventure, clap along with traditional Dominican music at a cultural performance, or explore the magical lagoons of the Indigenous Eyes Ecological Park.

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.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.

Cuba's top beach destination sits on a 13-mile-long peninsula with powder soft sands lapped by waters of the Kawama Channel. Resort hotels teem along the shore that U.S. celebrities and gangsters, including Capone, discovered in the 1920s. Clubs and bars provide mojitos and merriment, after long days baking on the beach, golfing, diving or deep sea fishing. Rent a scooter or hop aboard an open-air tourist train or bus to see more of this stunning spot. Caves, keys and virgin forest add to the area's allure.