Nearly crossing northern Italy from the Adriatic Sea westward, Emilia-Romagna gets its name from Via Emilia, the Rimini-to-Piacenza ancient Roman road it straddles. With a rich mix of age-old agriculture and modern industry, the region is home to many historic and cultural gems, both in its larger towns like Bologna, Modena and Ravenna, as well as in its many small hilltop villages. Of course, the region’s best offerings also include native culinary wonders like parmigiano cheese and tortellini.

Lucca's array of wonderfully intact historical sites makes it a must-see stop on any Tuscan itinerary. The mediaeval city walls still stand—you can hike or bike on top of them. Also visit the Duomo di San Martino and the Roman amphitheatre.

Go ahead and take that photo of yourself with a tilted hand "holding up" the Tower of Pisa. We won't tell; your rep as a sophisticated traveller will remain unblemished. Now that you've gotten that out of the way, climb the tower's 300 steps for a tilted view, or visit the National Museum of San Matteo and the Camposanto cemetery.

Everyone’s heard the Doors of Paradise, the Duomo, and Michelangelo’s David are captivating, but in Florence, beauty can sneak up on a traveller unexpectedly. You’ll duck into a random church to escape the heat only to spend two hours staring at an impossibly pure blue in a fresco. Or you’ll consider writing a sonnet about pear gelato. It’s just that kind of place. Don't miss the sunset over the Arno and the famous wines of the Chianti region just south of town.

A quick trip away from Ancona, the capital of the Le Marche province, pretty Senigallia is best known for its top-notch beaches—with velveteen sand and gentle tides, they’re perfect for families. The Rotonda a Mare, an art deco pier, is another highlight.

South of Garmisch-Partenkirchen on the Austrian border lies Germany's highest mountain, Zugspitze, rising nearly 10,000 feet and offering gorgeous glacier-top skiing. The towns of Garmisch and Partenkirchen used to be separate, but were merged for the 1936 Winter Olympics. With almost 75 miles of downhill runs of all difficulty levels, Zugspitze also has 68 miles of cross-country trails, a terrain park and Germany's first superpipe. It's super cool to say you were skiing in Garmisch, so be sure to spread the word upon your return.

Surrounded by water on three sides, Agios Nikolaos combines the sleepy feel of a seaside resort with all the amenities of a cosmopolitan port. Villas and tavernas spill over the town’s three hills to meet a harbour dotted with both mega-yachts and fishing boats.

Want to make your co-workers insanely jealous? Just casually drop "I’m holiday making in the Maldives this year" into conversation, preferably in the dead of winter. Or better yet, go there without mentioning it to anyone—then send them a "Wish you were here!" postcard.