Immortalized by Hemingway in “Islands in the Stream,” Cayo Guillermo is perched on Cuba’s north coast between the Bay of Dogs and the Atlantic. It is home to four all-inclusive resorts. Five miles of fine white sand and gorgeous, clear green waters, including the spectacular Playa Pilar, offer picture perfect sunning spots. Fantastic snorkeling and scuba diving opportunities beckon from more than six miles of coral reefs. Flamingos and many other birds live in its lagoons, forest and jungle.

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.

Travelers come to this small island north of mainland Cuba to bask in the sun, swim in sparkling blue water, and be pampered at an all-inclusive resort. To explore Cuban culture, you’ll need to go farther afield (this is a planned resort development; employees are bused in), but if you’re simply looking for a stress-free tropical break, Cayo Santa Maria might be perfect for you.

It’s not just for spring-breakers. Cancun, with its golden beaches and perfect climate, is the premiere coastal destination in Mexico. And while there is certainly a 365-day party available for college students, resorts cater well to families and to those seeking solitude. This Yucatan paradise is also the gateway to the ruins of Tulum and Chichén Itzá.

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.

Soaring mountains, jewel-coloured lakes and pristine wilderness await you in Canada’s first National Park. The irresistible beauty of the landscape invites travellers to immerse themselves in the outdoors all year round — whether hiking through untouched forests and paddling the turquoise lakes in summertime, or skiing the slopes and soaking in the steamy hot springs during the winter. Travellers also enjoy the warm hospitality of Banff or Lake Louise, the region’s charming mountain townships.

With Cascade Mountain to the north and Sulphur Mountain to the south, the town of Banff boasts a magnificent Canadian Rocky Mountain setting. Travellers are spoiled for choice by the irresistible combination of luxury lodges, perfect powder, renowned restaurants and energetic nightlife on offer. With both summer and winter appeal, Banff lures visitors to its stores, spas and slopes year-round.

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.)

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.

Old-world villages and story-book chateaux bedeck the Loire, once fought over by Gauls, Romans, Visigoths and even Attila the Hun. Hire bikes and roll through the lush valley, visiting fortresses in Amboise and Angers, UNESCO-designated Chartres Cathedral and the Gothic cathedral in Nantes. The Musée Jules Verne houses replicas of futuristic inventions designed by the author. Pay respects to other former residents: the Romans in Tours, the cave dwellers of Touraine, and the liberator of Orleans, Joan of Arc.

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.

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.

Stroll Las Ramblas and enjoy Barcelona's unique blend of Catalan culture, distinctive architecture, lively nightlife and trendy, stylish hotels. You'll find Europe's best-preserved Gothic Quarter here, as well as amazing architectural works by Gaudi. La Sagrada Familia, considered Gaudi's masterpiece, is still under construction (your entrance fee helps to fund the project). Feel like a picnic? Look no further than the rambunctious La Boqueria market, where you can stock up on local delicacies.