A captivating contrast of old and new, Luxembourg City's past is celebrated by its World Heritage status; its present sway by its position as headquarters for several significant European institutions. Small enough to explore on foot, this compact city offers a wealth of attractions, including dramatic promontory The Bock, underground passages in Petrusse Casemates, Palace of the Grand Dukes and the National Museum. Countless banks on Boulevard Royal, once a fortress moat, hint at the duchy's wealth.

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.

Lingering over pain au chocolat in a sidewalk café, relaxing after a day of strolling along the Seine and marveling at icons like the Eiffel Tower and the Arc de Triomphe… the perfect Paris experience combines leisure and liveliness with enough time to savor both an exquisite meal and exhibits at the Louvre. Awaken your spirit at Notre Dame, bargain hunt at the Marché aux Puces de Montreuil or for goodies at the Marché Biologique Raspail, then cap it all off with a risqué show at the Moulin Rouge.

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.

Conquering New York in one visit is impossible. Instead, hit the must-sees – the Empire State Building, the Statue of Liberty, Central Park, the Metropolitan Museum of Art – and then explore off the beaten path with visits to The Cloisters or one of the city’s libraries. Indulge in the bohemian shops of the West Village or the fine dining of the Upper West Side. The bustling marketplace inside of Grand Central Station gives you a literal taste of the best the city has to offer.

Any city that can be the butt of a Simpson's joke ("That's it! We're all going back to Winnipeg!") and simultaneously one of the most vibrant cultural centers in Canada is tops in our book. The city's history of isolation and self-sufficiency means that Winnipeggers are unpretentious and sincere (and fun-loving enough to name Homer an honorary citizen). Though the winters are long and cold, there are plenty of indoor activities to both keep you warm and stimulate your imagination.

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.