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.

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.

Amsterdam is truly a biker’s city, although pedaling along the labyrinthine streets can get a little chaotic. Stick to walking and you won’t be disappointed. The gentle canals make a perfect backdrop for exploring the Jordaan and Rembrandtplein square. Pop into the Red Light District if you must—if only so you can say you’ve been there. The Anne Frank House is one of the most moving experiences a traveller can have, and the Van Gogh Museum boasts a sensational collection of works.

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.

Campo dei Miracolo and Pisa's precarious tower are the main reason people visit this Tuscan city that traces its history back to around 1000 B.C. The grand buildings are relics of the former republic of Pisa's maritime might. Visitors can climb the Tower's 300 steps for a tilted view. Other spots in the city where Galileo was born include the National Museum of San Matteo and Camposanto cemetery. Local bus tickets can be bought at tabacs. An excellent rail network links Pisa with other Tuscan cities.

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?