One of Puglia’s most picturesque enclaves, Ostuni is known as the White City thanks to its plenitude of white-washed houses. A quick trip from the coast, the city is also celebrated for its labyrinthine streets, cathedral, and ancient defensive walls.

The southern Italian region of Puglia is symbolized by its white-tipped, cone-shaped trulli houses—and Alberobello, where more than a thousand UNESCO-listed trulli can be found, is the perfect place to discover them.

A Puglia port town that’s equal parts historic and functional, Monopoli makes a splash with medieval churches and castles jutting above the Adriatic. It’s also a painter’s dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.

A patchwork of vineyards and olive groves, dotted with whitewashed hill towns and sun-bronzed beaches—Italy’s southern heel has no shortage of photogenic landscapes. There are a few surprises, too, including the baroque city of Lecce and the Itria Valley, with its UNESCO-listed trulli houses.

One of Germany’s biggest and best-known resorts, Bavarian Alpine village Oberstdorf is popular with families year round. It’s home to Heini-Klopfer-Skiflugschanze, the world's second largest ski-jumping hill (and site of the famous "agony of defeat" ski-jump wipeout clip from ABC's Wide World of Sports). Nearby are the ski areas of Nebelhorn, Kanzelwand/Fellhorn and Kleinwalsertal.

Munich was almost completely destroyed in two world wars, yet it's managed to recreate much of its folkloric, Bavarian past. Oktoberfest is legendary, but you can visit the Hofbrauhaus any time of year for an immense beer. Olympiapark, the site of the 1972 games, is not to be missed (you can skate on the Olympic ice rink and swim in the pool). On a somber note, take time to visit the concentration camp at Dachau—it's an intense, yet unforgettable, glimpse into the not-too-distant horrors of the Holocaust.

Dating from at least the 10th century, today Kassel is most famous internationally as the home of Documenta, an every-five-years exhibition of modern and contemporary art. In the late 17th century Kassel received a large influx of Huguenot refugees from France. During the 1800s, it became the capital of the Brothers Grimm's Fairy Tale Route. In 1943, the city was virtually razed by British bombers, leaving few old sights, but the 18th-century Wilhelmshöhe Castle overlooking the city remains.

Located on the Bay of Biscay, La Rochelle’s history has mostly involved the sea, and today it has a large pleasure boat marina. Thus, its heart is the picturesque "Vieux Port" ("Old Harbour"). The city retains a rich architectural heritage, and has an aquarium, attractive gardens and a natural-history museum. Book early for summer; mid-July in particular features Francofolies, a huge French music festival.

Copenhagen is one of Europe’s oldest and most popular cities. It’s also one of the cleanest and most metropolitan. The dynamic Danish capital features progressive modern architecture, the must-visit Tivoli Gardens amusement park, stunning palaces, and all the activities and amenities you would expect in a world-class destination. Explore the canals and pretty narrow streets, appreciate beautiful old homes, and find great shopping and people watching on The Ströget.

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.