Southwest of London is Southampton (Soton to the locals), a metropolitan area centered around the port. However, tucked away on the side streets are ancient gems such as the Tudor House, Mottisfont Abbey, and "God's House," a museum located in a tower in the medieval wall. The ultra-modern Sea City Museum celebrates Southampton's seafaring past and the RMS Titanic. Looking for nightlife? Travelers can dance the hours away with bars, clubs, and live music, all accessible by public transportation.

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.

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.

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).

Encircled by medieval walls, Canterbury is doused in history. In the Middle Ages, Canterbury’s pilgrimage-site status made it the setting of Chaucer’s seminal "Canterbury Tales," while today, cobbled streets and the 6th-century Canterbury Cathedral secure this city as one of England’s must-visit destinations.

In the "city of dreaming spires", academia takes centre stage. Gaze out at Oxford's world-famous colleges from the top of St Mary's Church tower before heading into the city's pedestrian-friendly streets. The University's Botanic Garden and Ashmolean Museum are Britain's oldest. Follow your nose to the Covered Market for the makings of a picnic to enjoy on a punt or in the University Parks. Mix the historic and modern with visits to the 12th- century village church of Iffley and trendy Cowley's ethnic shops and music venues.

Amsterdam is truly a biker’s city, although pedaling along the labyrinthine streets can get a little chaotic. Stick to walking and you won’t be disappointed. The gentle canals make a perfect backdrop for exploring the Jordaan and Rembrandtplein square. Pop into the Red Light District if you must—if only so you can say you’ve been there. The Anne Frank House is one of the most moving experiences a traveller can have, and the Van Gogh Museum boasts a sensational collection of works.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?

Lisbon, the capital city of Portugal, has become an increasingly popular place to visit in recent years, with a warm Mediterranean climate in spite of its place facing the Atlantic Ocean. Full of bleached white limestone buildings and intimate alleyways, Lisbon's mix of traditional architecture and contemporary culture makes it the perfect place for a family holiday. Things to do in Lisbon: As Portugal's capital, there is a lot to see and do in Lisbon. Even exploring the city centre will take a few days out of a family holiday as there is no real central district, although Praça do Comércio is a good central place to start, in Baxia, or Rossio, the city's main square which has a sort of Trafalgar Square feel to it. Or you might try climbing up the Cristo Rei, a huge statue of Christ with spectacular views across the whole city. The Castelo de São Jorge also offers great views and isn't quite such a steep climb. A short tram ride to the west of Lisbon will also bring you to Belem, where you can explore attractions like the Belem Tower and the Belem Cultural Centre, which features a fantastic art collection including works by Dali, Picasso, Warhol and Magritte. In downtown Lisbon, you'll also want to visit the Gulbenkian, which has to be Portugal's answer to the British Museum full of fascinating cultural artifacts and with some superb gardens in the grounds. It's possible to have a fascinating educational family holiday in Lisbon, and there are also plenty of great beaches to work on your tan.

Anne of Green Gables! There, we got that out of the way. Besides chasing the famous fictional heroine, you'll find Charlottetown's own history, culture and nightlife keep you more than busy. Enjoy outdoor activities from golfing to boardwalk strolls and biking by day, and theatre and performance arts by night.

Quebec City may be the only fortified city north of Mexico, but it welcomes visitors with open arms. Explore the Citadel, where you might catch Canadian troops staging a military ceremony. As for food, you could splurge on afternoon tea at the Chateau Frontenac, or do as the locals do and snack on poutine—french fries with gravy and cheese curds.

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.

If you’re a history buff and a die-hard foodie, Chicago’s your kind of town. Take an architectural-history walking tour, then dine at Alinea (the most celebrated molecular-gastronomy restaurant in the U.S.). And don’t miss the Museum of Science and Industry, the biggest science museum in the Western Hemisphere.

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.