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.

Located on the shores of Lake Michigan, Milwaukee is perhaps best known for its famous breweries and the Major League Brewers, but there's more to the city than beer and baseball. Milwaukee is rich in historical and cultural attractions, making it the perfect place for a weekend of exploring. Check out the newly expanded Milwaukee Art Museum or the Mitchell Park Horticultural Society, which hosts an annual show of the same flora and fauna seen in Georgia O'Keefe's paintings. Those interested in the city's history can visit the grand Pabst Mansion, former home of one of the city's famous beer barons, or the Milwaukee Public Museum, to see what life was like in Old Milwaukee. If the kids are along, don't miss the Milwaukee County Zoo or the Betty Brinn Children's Museum. Of course a trip to the "Genuine American City" would not be complete without a tour of the Miller Brewing Company and a Brewers game at Miller Park.

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.

The Texas Rangers and Dallas Cowboys both make their home in Arlington. Midway between Dallas and Fort Worth, the city has long been home to Rangers baseball and now also hosts the Cowboys. Their state-of-the-art structure is the world’s largest domed arena. Visitors looking for other adventures can enjoy the original Six Flags Over Texas and Hurricane Harbor water park, along with shopping, golf and nightlife. Arlington also has a vibrant culture of live music, symphony, museums and theater.

Mansions and majestic hotels serve as reminders of Bar Harbor’s past (in the 19th century, it was a favorite vacation spot of society’s upper crust). Today, visitors kayak, explore Acadia National Park, go bird- or whale-watching, and enjoy salty sea air and sandy beaches.

A city trapped in time, Havana captures the imagination like no other. Faded glamour meets careful colonial-era reconstruction with a backdrop of irresistible color. Walk El Malecón, the walkway bordering the ocean; visit Old Havana and the Catedral de San Cristóbal; and listen for salsa music, open-air bazaars and parties that last all night.

Honfleur, a harbor in Normandy, was popular with Impressionist painters like Monet and Boudin. They found its changing light and picturesque quays inspiring—and even today, if you return to the same spot every day to take a photo, you'll find no two are the same. On Saturday, visit the town's lively market and stock up on local cheese.

So many of Madrid’s buildings look like castles, you’ll think you’ve stumbled into a fairytale. Even City Hall is astounding, with its white pinnacles and neo-Gothic features. A self-guided architecture tour can begin by the great bear statue in the central Puerta del Sol. Wander by the fanciful Royal Palace before absorbing the natural beauty of Retiro Park, then visit one of the city’s many museums. You could happily cap off each day by nibbling on forkfuls of paella while sipping Spanish rioja.

One of the world’s fashion capitals, Milan offers endless opportunities for chic shopping. Hit the artsy neighborhood of Brera for leather goods and Via Monte Napoleone for exclusive, expensive boutiques. The enchanting mosaics and glass vaults of Galleria Vittorio Emanuele II make shoppers feel like they’re wandering inside a painting. Take break from your spree to gape at the iconic Duomo, then grab tickets to a performance at La Scala. Post-opera, the Navigli district pulses with late-night activity.

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 traveler 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.