Hidden In Italy's Alps Is The Country's Northernmost Town Full Of Enchanting Medieval Shopping Streets

Italy is one of those countries where every region brings something different to the table. Whether it's the colorful canals of Burano — one of the most beautiful and lesser visited Italian islands that don't get enough attention — or the breathtaking shores of Levanto, an underrated Cinque Terre beach town, every corner of this country holds a magic of its own. But beyond the pristine coastlines and rolling vineyards, Italy's medieval history is just as rich — and often overlooked. Hidden away in the Alps, there's a gem that few travelers have heard of. Vipiteno, Italy's northernmost town, is a place where time seems to slow down. With its enchanting medieval shopping streets, fairytale architecture, and striking mountain backdrop, this South Tyrol destination exudes undeniable charm.

If you look up Vipiteno, you might get confused — why does it also go by Sterzing? And why do so many sites have both Italian and German names? That's because this town, situated near the Austrian border, has been pulled between two worlds for over a century. When South Tyrol was annexed to Italy in 1919, it divided a region that had long shared language and culture with Austria. Benito Mussolini tried to erase its German roots, banning the language, closing schools, and forcing Italian identity. Decades of unrest followed — protests, tensions, even bombings — but by the late 1960s, South Tyrol gained autonomy. Today, it has two names and speaks two languages, but it remains one unforgettable place.

Getting to Vipiteno isn't as complicated as you might think, and the route itself is a fun journey. Driving from Milan takes anywhere between four and five hours. Those coming from Venice will have a shorter ride — about three and a half hours. The great thing about Europe is that you have easy access to multiple countries, so if you've been admiring the water tricks of Hellbrunn Palace in Salzburg, Vipiteno can easily be a part of your Euro trip itinerary, considering it's less than three hours away. Alternatively, you can always take a train from Milan to Vipiteno, the ride being about four and a half hours long. And if you're traveling from far away, fly into Innsbruck Airport in Austria, the closest air hub to town.

As a year-round destination, every season in Vipiteno brings something special. Summer is all about fresh air, green peaks, and long days for hiking. Autumn turns the town into a scene straight out of a storybook, with red and gold leaves and lively harvest festivals. Winter brings heavy snowfall, twinkling Christmas markets, and some of the best skiing around at Rosskopf. Meanwhile, spring is quiet and peaceful, as flowers start to bloom and the town eases into warmer days.

Vipiteno knows how to make an impression. Its main street, Via Città Nuova, is full of colorful buildings, quirky little shops, and cafes serving up Trentino speck (a type of ham) that you'll want to sample. At the center of it all is the Torre delle Dodici, a 150-foot clock tower that's been watching over the town since the 15th century. Also referred to as Zwölferturm in German, this historic site once marked the city gate, and its bell still rings at noon.

For something you won't find on every postcard, head to the 15th-century Town Hall, a Gothic-style structure that boasts gorgeous wood paneling and a beamed ceiling. A quick 10-minute walk from there will lead you to the Civic and Multscher museums, where you can view pieces of the Alps' grandest and priciest altars. No visit to Vipiteno is complete without marveling at castles. Castel Tasso, or Burg Reifenstein, is one of the most impressive landmarks in the region, and the inside is even better than the outside. You can still see the kitchen in its ancient setup and the rustic furnishings of the dormitories. A little farther out is Castel Pietra, which stands proudly against the mountains. Although you can't tour the grounds, its dramatic silhouette alone is enough to make you stop and stare.

Vipiteno doesn't try too hard, and that's what makes it great. It's got the kind of old-world atmosphere that pulls you in without needing to shout about it — one medieval street, castle, and tower at a time. There are so many more of these towns worth exploring, like Atrani on the Amalfi Coast and Gubbio in the heart of Italy.