This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvellous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a mediaeval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.

Perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun,” gorgeous hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell'Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.

San Gimignano, known as the "city of beautiful towers," had 72 towers in its heyday. Now 14 remain, and, rising above Tuscany's Elsa Valley, they make the town look like a mediaeval dreamscape. Take in the fresco-covered Collegiate Church, the Civic Museum and the views from atop 177-foot Torre Grossa. Daytrippers from Florence tend to fill up the streets during the day, so for a more up-close-and-personal look at the town, spend the night.

One of the most popular regions in Italy, Tuscany stretches from the Tyrrhenian Sea to the Apennines. Its main cities include Florence, Pisa, Siena, Lucca, Arezzo and Livorno. Drive between stunning sites like Florence's cathedral and Uffizi Gallery and the Leaning Tower of Pisa. Or join a bike tour and pedal past sun-baked olive groves and vineyards. Don't miss the towers of San Gimignano or serene northern hill towns. For a more modern take, hit one of Florence's hip clubs, such as Space Electronic.

This picturesque Umbrian city has a history that spans many eras. The city wall and arch are Etruscan; the sixth-century Sant'Angelo church was built atop a Roman temple; the town's cathedral is both Gothic and Renaissance. If you have a sweet tooth, visit the famous Perugina chocolate factory; if you have a full set of sweet teeth, visit during the Eurochocolate festival, held in October, when the entire town reportedly smells of chocolate.

Centrally located Umbria's principal cities include Spoleto, Assisi, and Terni. The capital, Perugia, is famed for its chocolate. Take a tour bus or prepare for daredevil Italian drivers if you opt to rent a car. Assisi's Basilica has a host of treasures, including works by Giotto. The town is also home to the crypt of St. Clare, patron saint of television. St. Francis' meditation retreat is in the mountains to the north. Classes at Velia's Cooking Style in Terni make good use of local produce.

Winter sports enthusiasts will love Berchtesgaden, a village in the German Alps with several ski slopes and a top-notch bobsled track. Visit the Berchtesgaden Salt Mines (TripAdvisor travelers rave about their slides!). Nearby Lake Königsee makes a great day trip.

With half a million people, Nuremberg is Bavaria's second largest city. While its history dates to the 11th century, Nuremberg is most often linked to the 20th century (specifically World War II). It first served as the site of many pre-war Nazi rallies, then was nearly levelled by Allied bombing, then was the site of the famous post-war Nuremberg Trials. The city has much to offer today's visitors, including the rebuilt Nuremberg Castle and the world-famous gingerbread at Hauptmarkt. Hansel and Gretel would have loved this place.

Just north of Frankfurt at the foot of the Taunus Mountains, Bad Homburg has been treasured for its healing baths since the 19th century, when it hosted royalty from across Europe and the world. Of course they also came for its casino, sometimes called "the mother of Monte Carlo." Today, both the original Spa Park (or Kurpark) and the Bad Homburg Casino are still here, and visitors also enjoy Bad Homburg Castle and its White Tower. Just northwest of town is Saalburg, a restored Roman fort.

Just a few miles from the Slovak border in south central Poland, Zakopane is a resort town in the Tatra Mountains, popular with skiers in winter and with hikers and climbers year-round. In the late 18th and early 19th centuries, Zakopane grew into Poland’s most visible art colony, a hotbed of culture ended by Soviet influence after World War II. Today it harkens back to an earlier time, complete with gorgeous wooden houses. Learn about these buildings and more at the Museum of Zakopane Style.

Essen began in the mid-9th century as home to a women's abbey, then during the Renaissance became an important coal mining town and later a major steel production center. The famed metal-working Krupp family opened their first foundry here in 1810. One of Essen's most interesting places is the Zollverein Coal Mine Industrial Complex, once the largest colliery in the world. Now a UNESCO World Heritage Site, it attracts 800,000 visitors a year, often hosting art exhibitions and performances.

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.