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.Black Tomato

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.Black Tomato

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.Black Tomato

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.Black Tomato

Praiano

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.Black Tomato

Campo de’Fiori, Rome

For a glimpse of Roman day-to-day life, it has to be the vibrancy of Campo de’Fiori. Drawn in by the inviting smell of fresh baked bread, sit here with an espresso doppio in hand and watch as locals peruse the daily farmers’ market, shopping for everything from local cheeses to plump and juicy fruits and the best cuts of meat. Keep an eye out for market stalwart, Franca, whose family has been selling some of the market’s freshest fruits and vegetables for over 150 years.Black Tomato

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’.Black Tomato

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.Black Tomato

Dorsoduro, Venice

Tucked away behind the Chiesa Santa Maria della Salute, the cultural hub of Dorsoduro is a taste of the real Venice; that of the locals. The quiet streets lend themselves to an arty crowd, and bring a feeling of relaxed charm. Be sure to stop by the Gallerie dell’Accademia and the Peggy Guggenheim Collection before bedding down at Ca Maria Adele.Black Tomato

Varenna, Lake Como

Everyone always talks about Bellagio when it comes to Como, but that’s only because they haven’t been to Varenna. Overlooking the Lake’s most famous town, this quiet neighbor has an unpretentious charm with its old fishermen’s houses and picturesque waterfront.Black Tomato

Locorotondo, Puglia

Rolling effortlessly off the tongue, you need only say ‘Locorotondo’ to feel the allure of this beautiful Apulian village. This is not a town of grand attractions or famous tales, but that’s what makes it so irresistible. Calm and quiet, lose yourself in the myriad of side streets of a town that time forgot.Black Tomato

Santa Margherita, Cinque Terre

A jumble of pastel buildings, set overlooking the azure hues of sky meets sea and framed by tumbling geraniums and bougainvillea, Manarola is that scene straight out of a '50s postcard. Brightly painted fishing boats bob gently in the harbor to complete the scene.Black Tomato

Brera, Milan

In a city synonymous with slick design and effortless style, Brera typifies what it is to be Milano. A bohemian neighborhood of decades gone by, Brera now drips with sophistication. Pull up a chair at one of the al fresco spots on Piazza del Carmine and enjoy an aperitivo in what is easily one of Milan’s most attractive neighborhoods.Black Tomato

Camogli, Liguria

Camogli is the Riviera that the world forgot. You’ll find the same steep hillsides and pastel hued homes of the Cinque Terre, but what you won’t find are the crowds. Just sleepy enough to feel undiscovered but with enough local life and quaint trattorias to easily while away the days, this is a place to go before everyone else.Black Tomato

Matera, Basilicata

Limestone cliffs pockmarked as the surface of the moon, walking through the sassi neighborhoods of Matera has an almost otherworldly feel to it. Hewn out of the rock, the city is testament to regeneration with subterranean tunnels that once housed the poor and now takes the shape of UNESCO World Heritage sites, museums and luxury hotels. Stay for the night or just for an aperitivo; Materia is living history.Black Tomato

Rinella Bay, Salina, Aeolian Islands

Set to a backdrop of verdant hillsides and conical volcanoes, the beauty of the bay of Rinella is that peculiar kind, born out of contrast. Volcanic sands the color of night, are lapped by those aquamarine Mediterranean waters and perfectly offset by the pastel pink, blue, and white hues of the seafront villages.Black Tomato

Basilica San Miniato, Florence

While many will stop at the Cattedrale di Santa Maria del Fiore, continue uphill past the Piazzale di Michelangelo to the smaller, more intimate Basilica San Miniato. Clad in the same multi-colored marble of Santa Maria, the two may seem much the same at first but what sets San Miniato apart is the sweeping view that extends from the doorway over the city below.Black Tomato

Villa Cimbrone, Ravello

Arriving at Villa Cimbrone feels a bit like arriving at a grand party hosted by the Montagues or the Capulets. Faced with a towering set of doors, step through into this tranquil estate and stroll through the manicured gardens before coming to rest at the aptly named Terrace of Infinity, overlooking the Amalfi Coast in all its glory.Black Tomato

Mazzorbo, Venice

A short vaporetto ride from the buzz of Piazza San Marco, the lagoon island of Mazzorbo offers a slower pace of life in Venice. Come by during the day for a stroll through the vineyards and orchards before crossing over the bridge that links the island to the bright colors of Burano. Then, by night, stop by for the Michelin-starred cuisine of Venissa.Black Tomato

Church of San Biagio, Montepulciano

This Renaissance hill town is pretty idyllic no matter where you are, but for some of the most picture-perfect views of the Tuscan countryside, head to the Church of San Biagio located just below the city walls. Come autumn, when the sun sets and reflects off the crisping leaves; the sight is pure magic.Getty Images

Pantelleria

Ruggedly beautiful, Pantelleria has long been a favorite of in-the-know Italian society looking for an escape to somewhere altogether more secluded. Offering a whole new spin on wellness, head up to Lago di Venere where the warm waters form and volcanic mud form a natural spa at the heart of the island. Take a swim in the secluded coves that surround the island before holing up at the impossibly-chic Sikelia in a getaway that is about as off-the-grid as it gets.Black Tomato

Lake Orta

While the crowds head East to the better-known Lake Como and Maggiore, hang a left and check out Lake Orta instead. Smaller in stature and status, this is easily the Italian Lake District’s best-kept secret. Italians have dubbed it ‘Cinderella’ for so softly-spoken is its beauty that Orta takes on an almost mythical quality, such that even once you’re here, you can’t quite bring yourself to believe it.Black Tomato

La Maddalena Archipelago, Sardinia

If you sailed out from Sardinia’s Costa Smeralda, you would come across this cluster of islands and, until now, you would probably have kept on sailing. Why though? Dotted amid the larger islands, the tiny isolotti of the La Maddalena islands boasts some of the clearest waters and quietest beaches in all the Mediterranean. Stop off, it’d be rude not to.Black Tomato

Scilla, Calabria

Come for the Ancient Greek mythology, but stay for the local charm. The beaches here are well-known during the summer months, but less so are the tiny fishing villages of Chinalea and Scaro Allegio. It’s here that you’ll get a real sense for Scilla as boats bob in the harbor and fishermen tend to their nets while sharing a tale or two.Black Tomato

Spoleto, Umbria

A favorite haunt of Roman nobility, Spoleto has managed to hang onto its charm over the centuries and now makes for a tranquil day trip into the Umbrian hillside. Start in the medieval Upper Town with a visit to the Duomo, before making your way down through the modern Lower Town to the ancient city walls.Black Tomato

UNESCO Ravenna, Emilia Romagna

Home to a staggering eight UNESCO World Heritage Sites, Ravenna is hardly ‘under the radar’ but some places are well-visited for a reason. Combine the historical city with a killer gourmet scene and a stunning classical music festival and you get a sense of classic Italia as you switch your phone off and forget the emails for a few days.Black Tomato

Spiaggia delle Due Sorelle, Sirolo

The best beaches have always been those only accessible by boat and Spiaggia delle Due Sorelle is no exception. Years of being overlooked in favor of the Cinque Terre and Amalfi Coast has left this strip of coastline untouched and unspoiled. Pack a picnic-you won’t find anything else on this serene stretch of sand-and while away an hour or two.Black Tomato