THE 5 BEST Brighton Boutique Hotels

Boasting a historical dockyard housing Henry VIII’s Mary Rose and Lord Nelson’s HMS Victory, Portsmouth has maritime heritage written all over it. Museums aside, the city still lives and breathes the sea—best exemplified in its nautical spirit, cobbled historic district, and sail-shaped Spinnaker Tower viewpoint.

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.

Home to Windsor Castle, the second residence of Queen Elizabeth II, Windsor is a popular day-trip destination from London. Those who tarry in the riverside town fill their time wandering the cobbled streets, popping in and out of the luxe boutiques, restaurants, and tea shops that tumble down toward the Thames River.

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.

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.

Everyone who visits Paris for the first time probably has the same punchlist of major attractions to hit: The Louvre, Notre Dame, The Eiffel Tower, etc. Just make sure you leave some time to wander the city’s grand boulevards and eat in as many cafes, bistros and brasseries as possible. And don’t forget the shopping—whether your tastes run to Louis Vuitton or Les Puces (the flea market), you can find it here.

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.

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.

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.

At the shore in Miami Beach, visitors can swim, surf and jet ski in the warm and crystal-clear Atlantic waters. You can also nap on the white sands, work on a tan or simply watch the beautiful people, especially at South Beach, a favourite of models and celebrities.

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.