The Most Beautiful (and Under the Radar) Places to Visit In Italy

  • April 28, 2022
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These stunning locations are perfect for your next vacation—and far from any tourist trap.

Italy is one of the most popular vacation destinations in the world, and it's no wonder. However, not every Italian getaway needs to be in the hub of Florence or along the Amalfi Coast. Here, we take a look at some of the most beautiful—and under the radar—places in Italy to book your next vacation to.

Tom Marchant is the co-founder of luxury travel company and trip planner, Black Tomato, which delivers luxe experiences around the world via inspiring itineraries and access to the globe's up-and-coming, remote destinations. Marchant's finger on the pulse of travel trends and the world's best in hotels, restaurants, destinations, and honeymoons is unique and incomparable–and he's sharing his expertise and curated lists of where to visit, stay, eat and more with

Via Krupp, Capri

While the risk of tumbling rocks means you can no longer stroll the elegant switchback bends that make up Via Krupp, that doesn’t stop the view at the top from being any less spectacular. Head up to the Augustus Gardens and gaze out at the best of Capri laid before you.

San Cassiano

Not only is San Cassiano the epitome of alpine charm (think wooden-clad chalets with castle-like turrets), but it’s also home to a rich Ladin culture and a consequently authentic South Tyrolean experience. Soak it all in from a rustic-luxe loft suite at Rosa Alpina.

San Gimignano, Tuscany

Serving up some of the country’s best gelato (an accolade that isn’t given out freely), an afternoon in San Gimignano is always one well spent. The hilltop town provides a relaxed antidote to the bustle of Siena and with its enchanting views across the cypress-topped hillsides, it feels a million miles from city life.

Isola Bella, Sicily

Tucked away in a quiet cove and joined onto the mainland by just a narrow strip of land, Isola Bella is a pinprick of an island with more than its fair share of natural beauty. So-called ‘The Pearl of the Ionian Sea’, wait for low tide before heading across the island to discover hidden sea grottoes and pebbled beaches in a place that will feel all your own.


Delicately perched on the cliff face, equidistant from Amalfi and Positano and just a short drive from the effortless romance of Ravello, Praiano is my go-to whenever I visit this sun-drenched stretch of coastline. Not just for the saunters down to secluded coves or the glasses of prosecco at beachside bars in Vivaro and Fioriere, but for a stay at Casa Angelina where the crisp decor and serene views always leave you floating on cloud nine.

Bologna, Emilia-Romagna

Bologna is one of those places that really comes into its own come sunrise and sunset. Clad in terracotta, the shifting sun adds a whole new dimension to the city as those red hues are lifted and bathed in a golden light, most befitting of the city nicknamed ‘La Rossa’.

Ostuni, Puglia

Puglia has long been a favorite of mine and each time I visit, I love to get to know it better. A few years ago, my curiosity took me into the tiny village of Ostuni and what I found there has brought me back ever since. A white-washed hilltop town, it could be Greece on first glance but come around 8 or 9PM in the summer, when local families spill out onto the street to enjoy a meal al fresco in the balmy evening sun; you’re left in no doubt that this is Italy at its purest.

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