1. Pietrasanta

Located in the northwestern corner of Tuscany, just an hour and a half from Florence, (and a mere three kilometers from the coast) the gemlike medieval town of Pietrasanta won my heart the moment I stepped through the ancient gate of Porta a Pisa and found myself in the striking main square, Piazza del Duomo.

Although I first encountered this singularly beautiful town years ago, I can still recall the very first moment I fell in love. It was late afternoon and I sat down at one of the many lively outdoor cafes. I remember being instantly mesmerized by the dramatic contrast between the rectangular geometry of the piazza, the soaring white façade of the Duomo, and an installation of large, unexpectedly modern sculptures. I soon learned that the sculptures change frequently and, that this small town has a huge, worldwide reputation as a mecca for artists and art lovers.

Not only is Pietrasanta known for its proximity to the famed Carrara marble quarries where Michelangelo hand-selected the white marble for his inimitable Pietá, it is now a satellite hub of the international art world. Nicknamed “Little Athens” or the “City of Artists”, the town’s profusion of sculpture studios, foundries and art galleries are teeming with works by celebrated artists including Henry Moore, Isamu Noguchi, Igor Mitoraj, Joan Mirò, Fernando Botero, Damien Hirst and scores more, who have come here to work and to live.

If art and architecture are important to you, I cannot recommend this magical place highly enough. And when it’s time sit and process all you’ve seen, a quiet aperitivo in scenic seaside Forte dei Marme awaits, mere moments away.

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2: Ravenna

An hour’s drive or train ride from Bologna, in the Emilia Romagna region, is a city unlike any other called Ravenna.

An art and history lover’s paradise, ravishing Ravenna was once the capital of the Western Roman Empire, then the capital of the Kingdom of the Ostrogoths and finally a privileged province of the Byzantine Empire. The evidence of this glorious past is everywhere you look, embodied in its remarkable, pristinely preserved architectural treasures and the spectacular 5th and 6th century mosaics that adorn them. Eight of these structures and their precious mosaics are designated as UNESCO World Heritage monuments.

For me, visits to the Basilica of Sant’ Appolinare Nuovo, the Basilica of San Vitale and the Mausoleum of Galla Placidia are essential on every trip. The Mausoleum is my absolute favorite. From outside it appears to be a small unassuming brick building, while inside awaits a breathtaking surprise... the most gorgeous and impressive mosaics I’ve seen in Ravenna or anywhere else!

A sidenote: when composer Cole Porter visited Ravenna in the late 1920s, the Mausoleum’s Night Sky mosaic with its 900 glittering stars inspired him to write the perennial classic Night and Day. Ravenna will surely inspire you too!

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3: Urbino

Three and a half hours by car from Rome or 2 hours from Bologna, this UNESCO World Heritage Site perched atop a hillside in the Marche region is a perfectly preserved walled city and, one of the most important Renaissance sites in Italy.

My personal connection to this evocative place is deeply rooted in my family...it is less than an hour’s drive from Pesaro, my father’s birthplace on the Adriatic Coast, where we still spend summers. Every year, generally on a cool, cloudy day when I can bring myself to leave the beach, I drive to Urbino through the peaceful landscape. The drive itself is a delight and when at the very last turn, Urbino appears as if by magic, it never fails to bring tears to my eyes.

This is the city where revered Renaissance architect and artist Raphael was born; the influence of Urbino’s grace and light still illuminate his paintings. I always revisit the National Gallery of Le Marche in the Palazzo Ducale, hailed as one of the most impressive examples of Italian Renaissance architecture. Significant works by Raphael and many other Renaissance masters are displayed here. I adore the painting “Ideal City” attributed to Piero della Francesca, but you will surely discover your own favorite.

Urbino today is a lively town boasting one of the oldest universities in Italy. A stroll through its charming narrow alleyways and porticos will make you feel as if you are in a medieval fairy tale. Even if your time here is limited, don’t miss a stop at any one of the many cafes or trattorias to taste the traditional crescia, a flaky flatbread stuffed with wild greens, grilled vegetables, local charcuterie, sausages, and cheese. Personally, I dream about the version filled with soft stracchino cheese, arugula, and tomatoes.

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4: Pienza

Halfway between Rome and Florence, in Southern Tuscany, tiny Pienza is quite simply the most perfect town I know. To be honest, I’m not sure I can explain what makes it so delightful. I do know that even getting there is pure bliss!

The route through the Val de Orcia (Orcia River Valley), one of the most picturesque areas of Southern Tuscany, is a panorama of winding hills and roads lined by cypress trees, vineyards, olive groves and in summer, endless golden fields of wheat and sunflowers...an unforgettable prelude to arriving in this magical place.

With its scant population of 2,000 residents, Pienza is known as the “Ideal Renaissance City”. It was designated a UNESCO World Heritage status for its 15th century “model” urban design, architecture, and graceful historic center. But for me, one of the things that makes Pienza so exceptional is its hilltop location, overlooking the single most beautiful view of the Tuscan countryside anywhere.

This is a town made for what we call in Italian, “passeggiare” or strolling. I love exploring its harmonious, warm-hued historical center and getting lost in the countless ivy-draped streets surrounding it, their doorways framed by pots of flowers...or walking past happy people chatting over coffee or lunch at the cafes and restaurants in each enchanting square.

On each visit, I have a ritual of finding the three small, but enormously charming streets that legend says will bring romance and good luck: Via del Bacio (Kiss Street), the famous Via dell’ Amore (Love Street) and Via della Fortuna (Good Luck Street). I urge you at the very least to find your way to Via del Bacio — a sure bet for a fabulous photo, given its stupendous views over the Val d’Orcia.

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Many tourists skip Pienza in favor of well-known towns like Montepulciano and Montalcino, but please trust me, if you’re within reach, this is the place!

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5: Civita di Bagnoregio

In the region of Lazio, (a one-and-a half hour drive from Rome, and 30 minutes from Orvieto), sits the surreal 2,500 year-old Etruscan village of Civita di Bagnoregio. A UNESCO protected site, it feels as if it’s literally suspended in time and space. Hovering on the border between Lazio (where Rome is the capital) and Umbria, it is one of the most scenic and intriguing villages in Italy.

Known also as “the dying city” (la citta’ che muore), Civita perches atop a canyon of crumbling volcanic tuff that rises from the Tiber River Valley, where it faces the constant danger of destruction due to erosion. This miniscule village hosts a population of 100 in the summer and about 12 during the winter.

Even getting here is an adventure, as it is accessible only via a 300-meter pedestrian suspension bridge. It’s an unforgettable walk to a place that will always stay with you.

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I vividly remember my first glimpse of Civita as a child. Looking across the valley from a panorama terrace, the town seemed to be floating in mid-air. To my young eyes it seemed both eerie and enchanting, like a vision from a dream. Years later I returned as an adult and fell totally in love with this impossibly poetic place.

Entering the town through the gate of Porta San Maria you’ll wind through a cluster of pretty houses decorated with wrought iron balconies, creeping ivy, and overflowing flower boxes to the main square. There you’ll be greeted by the stately Romanesque church of San Donato.

I suggest a leisurely wander to soak up the atmosphere and admire the wonderful architecture spanning several hundred years of styles, including some surprisingly elegant Renaissance palazzi. And leave time to enjoy the excellent small trattorias, cafes, and shops of local artisans.

I can say from experience that your visit will truly be a high point!

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If you are ready to discover an Italy you’ll never forget, visit Discover my Italy for information about our spectacular small group tours or working with us to custom design the trip to Italy of your dreams!

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