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.

A city trapped in time, Havana captures the imagination like no other. Faded glamour meets careful colonial-era reconstruction with a backdrop of irresistible colour. Walk El Malecón, the walkway bordering the ocean; visit Old Havana and the Catedral de San Cristóbal; and listen for salsa music, open-air bazaars and parties that last all night.

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.

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.

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.

Who cares about a little fog (okay, a lot of fog) when there’s so much to do in San Francisco? By day, explore Fisherman’s Wharf and the Aquarium of the Bay, ride a cable car, and stroll around the Presidio; by night, have a fabulous dinner (at a Michelin-starred restaurant or a tiny place in Chinatown), then hit some of the best clubs on the West Coast.

It’s no wonder Napa made three of our lists this year… it might just be the world’s most perfect spot for a weekend getaway. What more do you really need than romantic inns, great food and wine, and relaxing spas?

<p>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. </p><div>Things to do in Lisbon </div><p>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. </p>

Iceland’s biggest city, Reykjavik bears the distinction of being the world’s northernmost capital, and for virtually every Icelandic visitor it serves as a gateway, just to the city itself or to the rugged adventure options beyond. Founded in the country’s southwest at the end of the 18th century, Reykjavik has been Iceland’s cultural hub ever since. These days, that culture includes a hip and internationally recognised music and arts scene, not to mention a notoriously wild nightlife.