Featuring white-sand beaches, volcanic peaks, and protected parks, along with some of the most impressive dive spots in the world, Guadeloupe is an island hopper’s paradise. This French archipelago is one of the Caribbean's best-kept secrets, offering a more relaxed alternative to its better-known neighbours.

Antigua has hundreds of beaches, from the bustling Pigeon Point to the kitesurfing paradise of Jabberwock Beach. It's fun to mix it up—a day spent in a secluded cove, another spent people-watching at a tourist magnet. When you’re tired of sun and sand you can shoot ‘em up at Reservoir Range, where archery and air pistols are a fun way to work out any lingering pre-holiday stress. A tour of the Antigua Distillery is a spirited way to experience a true taste of the island.

Lively Antigua and Barbuda move to the music of steel drums. You can visit a different beach each day and not repeat yourself for a full year—and that's why tourists and celebrities alike flock to this sun-soaked Caribbean island. Take a day cruise, rent some diving gear or cruise up the beach on a Segway for a real adventure, island-style.

In St. John's, the capital city of Antigua, farmers markets, candy- colored architecture and the ruins of sugar plantations vie for attention with a kaleidoscope of coral reefs and sailing adventures. Salute the white baroque towers of St. John's Cathedral that dominate the skyline before joining the flocks of cruise passengers on a Heritage Quay shopping excursion. To experience the island's early cultures, visit the Museum of Antigua and Barbuda, housed in a 1750s colonial courthouse.

With attractions and activities galore, Chicago is everyone's kind of town. See all the famous sights, then go to a show in the theatre district or a Cubs game at historic Wrigley Field, followed by a late-night visit to a blues club or jazz bar. Culture hounds will delight in the multitude of museums, including the prestigious Art Institute and the Chicago Historical Society. Families will find plenty to do at Navy Pier and plenty to explore at the Field Museum and the Lincoln Park Zoo. You could spend all day strolling through Hyde Park or shopping along the Magnificent Mile. Discover vibrant ethnic neighbourhoods, architectural landmarks, delicious food and world-class hotels. From the top of the Sears Tower to the shores of Lake Michigan, Chicago offers so much to do, visitors keep coming back for more.

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.

The town that gave the country (and port wine) its very name, Porto is Portugal’s second-largest metropolis after Lisbon. Sometimes called Oporto, it's an age-old city that has one foot firmly in the industrial present. The old town, centered at Ribeira, was built on the hills overlooking the Douro River, and today is a UNESCO World Heritage Site. The 14th-century São Francisco church is a main attraction, as are the local port wine cellars, mostly located across the river at Vila Nova de Gaia.

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.

Roman legions marched into what is now the Rhineland's largest city in 38 B.C. These two thousand years have produced a wealth of sites to visit, from Roman towers to Gothic churches to modern architecture. With a reputation as a fine art center, Cologne has museums running the gamut from the Museum of Applied Art to Museum Ludwig, home to works by Warhol and Picasso, to the Chocolate Museum. The city has an excellent bus, tram and train system, on which Kolner Tageskarte, Day Tickets, are valid.

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?