Ciao, Italy

Pizza, vino, ages old art, and ancient architecture all come to mind when we hear the word “Italy.” While there’s of course plenty to see along the well-trodden tourist paths that weave through the immense sea of famous Italian wonders that people from all over the world flock to see, there’s so much more to Italy than that. The thing about the well worn path is that so much of what the path doesn’t touch remains uncharted territory to visitors, just begging to be explored. If you’ve got a wandering soul, take a trot through these Italian gems and get lost, in the best way possible.

Milan, Italy

Yep, it’s true—Milan is certainly one of the fashion hubs of the world and is often left behind when it comes to touring Italy, and with good reason. Unless you really have the time to dedicate to getting to know the city, Milan feels cold, daunting, and hollow, which it can be. However, once you peel back her prickly outer layers, Milan will reveal wonders that one can only find in this special place. You’ll fill your time with things like taking a spin down Corso Magenta to marvel at all the beautiful homes before stumbling upon the museum that houses the Last Supper; things like cruising along the Metro’s Yellow Line and getting off at the Duomo stop, entering into a world that blends history and modernity, whose piazza sports a black and gold McDonald’s, forced to conform to the branding standards of the surrounding stores in true Italian style. You’ll find yourself eating the best aperitivos ever for eight euros and drinking beer at Bar Frida, listening to live music surrounded by local art. If you only have a few hours or just one day, you really should skip Milan—you’ll hate it. But if you have more time to dedicate to her, getting lost in this diamond in the urban rough will delight you.

Positano, Italy


Practically everyone has heard this by now, but it’s still as true as can be: “Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.” This is how John Steinbeck described this glimpse of heaven on the Amalfi coast in a piece for Harper’s Bazaar in 1953, and not much has changed. While Positano isn’t that far from the tourist trail that includes Cinque Terre, one can spend hours, even days, wandering the winding, stair-filled streets that compose Positano. A popular vacation spot for affluent Italians, there are shops and cafes galore along the main road that will satiate your tastebuds time and time again. When walking tires you out, rent a moped—nothing will acquaint you more with Italian living than taking on its traffic. At the end of every day in Positano, you’ll find yourself glowing like Diane Lane in Under the Tuscan Sun.

Bologna, Italy


Home to one of the oldest universities in all of Europe, Bologna is both an academic and cultural wonderland. You’ll get your fill of famous Bolognese sauce that was originally developed there, as well as mortadella, the cold cut-esque meat that has transformed into what Americans now know as bologna of the sandwich variety. Roam the streets listening to young students chatter and wander into amazing cafes like Ranzani 13, brimming with all the pizza and birra you can handle within their mirrored and chalkboard-covered walls.

Palermo, Sicily


Although Sicily is autonomous, it’s still a part of Italy, so, luckily, Palermo can still make this list because it’s not to be missed. Most travelers don’t get off of Italy proper, so even just venturing to Sicily is a unique experience in and of itself. Flying is an option, but the ferry is so much more fun—you’re practically guaranteed at least two crazy travel stories to come out of it. It’s a highly Catholic area, so expect churches galore and a modestly dressed population. While Palermo can be a little rough around the edges, it’s a whole other version of Italy that has to be experienced. Mill around this city for a few days and you’ll have a brand new view of how diverse the country really is, and you’ll likely have encountered a couple of tough-as-nails Italian grandmothers along the way as well that will leave you with #lifegoals.

Entracque, Italy


If you leave Italy without experiencing the Italian Alps, you’d hardly be able to call your journey complete. This tiny place is just outside the French border, so you’ll feel that influence everywhere you go. With just under 900 residents, Entracque is about as quaint and charming as it gets. If you’ve ever wanted to pick up skiing, or you’re just in it for the chocolata calda, the sheer beauty of this place will blow you away day after day—you’ll have no trouble getting lost in this winter wonderland.