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.

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.

Sure, you can leave the sunny sands in favor of a crocodile watch or horseback ride, but when the main strand is called Seven Mile Beach, it's clear what draws most visitors to Negril. Depending on how much sun you want, you're welcome to go topless or even sunbathe in the buff in some places.

The Dominican Republic lies in the same waters as Cuba and Puerto Rico, taking up the eastern two-thirds of the island it shares with Haiti. Offering a lush interior with a mix of caves, Victorian gingerbread houses and the lore of pirates, plus 900 miles of coastline along its brim, island highlights include riding a cable car up Mount Isabel de Torres and basking on stunning Saona Island. Oh, and did we mention the D.R. is family-friendly, has just about perfect weather and is affordable?

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.

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?

To the first-time visitor, Palermo is a city of ever-changing character. An abundance of dusty museums, Arabian domes and flourishes of baroque splendor jostle with boisterous markets, chaotic traffic and oppressive summer heat. The Sicilian hotspot is a noisy, polluted, often dangerous, but always fascinating city. Don't miss marvels of Arab-Norman architecture, such as 12th-century Palazzo dei Normanni or San Giovanni degli Eremiti. Ask your hotel to arrange cabs and negotiate fares before setting off.