Top 10
Top Ten Italian Towns

Italy abounds with spellbinding towns in idyllic settings. As with all my Top Ten lists, these are not placed in order of preference.

1. Siena – Tuscany

   Situated in the heart of Tuscany in the Chianti wine region, Siena has its roots in the Middle Ages. At its center sits Piazza del Campo, renowned for the annual Palio delle Contrade, a bareback horse race that originated in the early 15th century. Thousands of spectators pack the square to watch the race, which consists of three laps around the piazza at breakneck speed and lasts for all of ninety seconds.

   
   
   
   

   
   
   
   

   The maze of cobbled streets that lead off the piazza in every direction is a pure delight. Most are traffic-free and brimming with a wide variety of irresistible small boutiques, gelateria, restaurants, pasticceria (pastry), and coffee shops. I love shopping in Siena. It has an intimate, invigorating atmosphere versus Florence, which is larger and has become overrun with tourists other than in the winter offseason.

   
   
   
   

   
   
   
   

   
   
   
   

   
   
   
   

   The Duomo on Piazza del Duomo is breathtaking. The façade is adorned with pale pink carved bands of marble, while the interior has a forest of soaring zebra-striped marble columns.

   
   
   
   

   
   
   
   

   The floors are embedded with inlaid marble scenes depicting mythological and biblical subjects.

   
   
   
   

   The Piccolomini Library inside the Duomo is not to be missed for its exquisite frescoes.

   
   
   
   

2. Lucca – Tuscany

   Old Town Lucca is wrapped in defensive walls originally constructed in the Middle Ages. The Renaissance era walls that one sees today are the most recent and the best-preserved defensive ramparts in Europe. A two-and- a- half-mile walk atop the walls – beneath the shade of plane trees – treats one to a bird’s-eye view of the entire town. It’s a perfect orientation to this seductive town.

   
   
   
   

   Piazza dell’ Anfiteatro is an elliptical square ringed by private homes, boutiques, and outdoor cafés. Built between the 1st and 2nd century BC as a Roman amphitheater, it held thousands of cheering spectators. Today one can still identify signs of its original purpose in several remaining archways, which puncture the piazza’s outer walls.

   
   
   
   

   Lose yourself in the cobblestone streets where centuries-old churches overlook tiny medieval piazzas and 21st Century restaurants; enjoy the upscale boutiques; purchase some ‘olio d’oliva Lucchese,’ Lucca’s superior olive oil from the olive groves beyond the Old Town’s ancient walls. Visit a café in Piazza Napoleone, Piazza San Michele, or Piazza dell’ Anfiteatro. Sip a cappuccino or a glass of wine accompanied by local cheese and olives and take in the ambiance – the theater of life in this gorgeous Italian town. And speaking of theater, Lucca, the home of Puccini, is well known for its roster of music festivals between July and September. From jazz and rock, to classical music and opera, the town comes alive with music.

   
   
   
   

   
   
   
   

3. Portofino

   The fishing town of Portofino sits on a promontory of the Ligurian coast thirty miles southeast of Genoa. At its center is a half-moon harbor hugged by a pastel-colored palette of houses.

   
   
   
   

   Luxury hotels, upscale boutiques, and seafood restaurants line the piazetta (little piazza); pleasure boats, fishing boats, and opulent yachts of the world’s rich and famous rest in the water.

   
   
   
   

   Portofino is so picture-perfect that it seems more like an idyllic movie set than a thriving harbor village where locals enjoy their evening passeggiata and jet setters linger over cocktails on the decks of their luxurious boats or at harbor-front cafés.

   
   
   
   

   
   
   
   

   Portofino National Park was initially founded to create a simple path that would link Camogli, Santa Margherita, and Portofino. Hiking trails lead one through ever-changing terrain, past olive groves, lush forested areas where an abundant variety of plant life thrives, tiny hamlets where farmers tend their land, and views of the emerald blue sea and rugged coves.

   Take a walk along the shaded pathway that leads uphill from the harbor to the delightful Museo del Parco and outdoor sculpture garden that features contemporary, international artists’ works.

   
   
   
   

   
   Hike up to Brown Castle for sensational panoramic views of Portofino.

   
   
   
   

4. Assisi – Umbria

   Assisi, sitting on a lofty hill overlooking the Umbrian countryside, has a unique aura of serenity.
   The spirit of St. Francis – who was born and lived out his life in Assisi – hovers over the town. He was a lover of mankind, animals, birds, and nature.

   
   
   
   

   The entrance to the Old Town is framed by an archway that takes on a pink hue as the early morning sunshine caresses its ancient stones. A tree-lined promenade flanked by stores leads to the piazza where birds perch on the edge of the fountain, locals chat at espresso bars over their early morning coffee, and neighbors stop to greet each other while walking their dogs. By mid-morning, the piazza is crammed with tourists following their umbrella toting guides. Get there early, and you’ll be one of only a handful of visitors.

   
   
   
   

   
   
   
   

   
   
   
   

   While wending your way along the narrow streets towards Basilica di San Francesco d’Assisi, notice the frescoes and the views framed by ancient stone archways.

   
   
   
   

   
   
   
   

   The simplicity of the Gothic style Upper Basilica in the church of San Francesco, gives it an atmosphere of tranquility not found in more opulent Italian churches. Its soaring walls are covered from floor to ceiling with twenty-eight frescoes painted in muted colors depicting the life of St. Francis. The majority of the artwork is attributed to the great Italian masters Cimabue and Giotto.

   
   
   
   

   In The Lower Basilica, designed as a massive crypt with ribbed vaults, the frescoes that blanket the walls have been expertly and painstakingly restored.

   
   
   
   

   As you walk the cobbled streets, pop into the stores that sell exquisite inlaid marble tabletops, the art galleries, trendy boutiques, and indulge in irresistible Assisi pasticcini (pastries).

   
   
   
   

   
   
   
   

5. Orvieto – Umbria

   Orvieto rests on an isolated plateau of volcanic rock above soaring tufa cliffs. This impenetrable town surrounded by defensive tufa walls dates back to Etruscan times. With its limited size and no room for expansion, it has retained its unique, intimate charm.

   
   
   
   

   
   
   
   

   I highly recommend that one spend a night or two in Orvieto at one of the reimagined Renaissance palazzos. The early mornings and late afternoons/evenings when the tour buses depart, and the locals are going about their daily routines, are magical. Linger over a glass of Orvieto’s renowned white wine while taking in the evening passeggiata and children playing in the piazzas. Browse the art galleries, ceramic stores, jewelry, linen, and interior design stores.

   
   
   
   

   
   
   
   

   
   
   
   

   
   
   
   

   Choose a restaurant in one of the hidden courtyards or narrow alleys and imbibe the vibe of dinner in a romantic setting.

   
   
   
   

   
   
   
   

   
   
   
   

   Don’t miss Orvieto’s Duomo, which is listed as one of Italy’s top five cathedrals. Mornings and evenings when the sun’s gentle rays illuminate the gold, blue, and rose colored mosaics of the façade and the massive bronze doors, are the perfect time to savor the beauty of the magnificent cathedral that combines and balances both Gothic and Romanesque styles. Enjoy your morning coffee on the piazza gazing at the cathedral, then explore the interior with its exquisite frescoed walls and ceilings, sculptural masterpieces, and the Brizio and Corporale side chapels.

   
   
   
   

   
   
   
   

   
   
   
   

   
   
   
   

   Orvieto has over 1200 underground caves, tunnels and wells, many of which date to Etruscan times. At times they were used when the city was under siege but also provided additional space for storage, workshops, and oil presses. A guided tour will lead you through this centuries-old hidden world.

   
   

   courtesy of atlasobscura.com

   
   

6. Positano – The Amalfi Coast

   Drive the Amalfi Coast along the narrow road which snakes beneath lofty tufa formations and offers tantalizing views of crystal-clear waters and sandy coves below. The antics of drivers who maneuver buses, SUVs, and trucks past one another is like an ongoing Italian comedy. It involves gesticulating, arm-waving, cursing, muttering, joking, and laughter.

   
   

   
   

   ‘Po-sitano, the artists’ paradise the paradise of the artists.’ That poetic refrain delivered in a sing-song tone has stuck with me since I was nine years old and caught my first glimpse of Positano. Our guide repeated it over and over again as our tour bus approached Positano.
   In late September, this idyllic Italian town that cascades down the mountain like a multi-teared birthday cake was ablaze in color and a hive of activity.

   
   

   
   

   In the cluster of lanes, bright yellow lemons bursting with juice sat beside bottles of Limoncello; at the fruit stand, perfect, plump, juicy Sicilian peaches blushed in the late summer sunshine; technicolor beach ware was displayed in outdoor stores; flowering vines wrapped themselves around patios; a picture-perfect salumeria (delicatessen) perched atop a flight of stairs in a tiny piazza.

   
   
   
   

   
   
   
   

   
   
   
   

   
   
   
   

   I recommend Hotel Bucca de Baco perched over the beach beneath the green-domed church of Maria Assunta, the hallmark of Positano. Our suite overlooked the emerald blue sea and the beach, dotted with bright green and orange umbrellas and chaises lounges.

   
   

   
   

   At night, Positano sparkles like a fairytale town. Restaurants spill onto those tiny, winding roads. Diners stand up to move their chairs out of the way of the Sita buses that come and go.

   
   
   
   

   
   
   
   

   Animated balladeers wander among the guests uniting restaurant staff and diners in spontaneous camaraderie.

   
   

   
   

   On a night lit by a full silver moon, Positano IS the artists’ paradise, the paradise of the artists.

   
   

   
   

7. Ortygia Island – Siracusa – Sicily

   Ortygia Island is an ancient gem said to have been ruled by the mythological sea goddess Calypso, daughter of Atlas. It is reached via Ponte Nuova, a mile-long bridge that links it to the mainland.
   The ruins of the Temple of Apollo in Piazza Pancali, built in the early 6th century, is the oldest Doric temple in Western Europe. An inscription to Apollo – god of music, poetry, art, truth, sun, and light – on the top step of the temple base provides evidence that the temple was dedicated to Apollo.

   
   

   
   

   The island is a marvelous blend of its ancient Greek origins (the Greek mathematician Archimedes was born here) and its Italian heritage that dates back to 212 AD when Siracusa fell to the Romans.
   The Duomo, which dominates the unique V-shaped Piazza del Duomo, was built atop the ruins of the Temple of Minerva. Here, multiple architectural styles intertwine with the combination of massive Doric columns of a pagan temple and an elaborate Italian baroque façade.

   
   

   
   

   Piazza Duomo, surrounded by elegant palazzos, is one of the most beautiful in Italy. The outdoor restaurant beneath Palazzo Beneventano del Bosco – opposite the cathedral – entices one to order a drink and stay awhile.

   
   

   
   

   An ancient sea wall surrounds Ortygia Island. Within these walls are a treasure trove of boutiques; tiny, superb, family-run restaurants; and the open air market bursting with exuberant colors that offers an impressive variety of the freshest seafood and fruit ripened to perfection.

   
   

   The view from my balcony at hotel Domus Mariae.

   
   

   
   

   A SicilianStreet Market

   
   

   Foro Italico – the seaside promenade – while rich in ancient Greek mythology, is also the most gorgeous location on the island to watch a Sicilian sunset when the sun hovers over the horizon before setting in a blaze of gold. Choose a waterfront restaurant and idle over a platter of antipasti accompanied by a glass of wine while taking in the bewitching beauty of your surroundings.

   
   
   
   

   
   
   
   

   Adjacent to Foro Italico is Fonte Arethusa (Arethusa Spring). Legend has it that the river god, Alpheus, fell in love with Arethusa, the sea nymph, who turned into a water-spring. Alpheus became a river, and the lovers were united in the waters. Today it’s also renowned for its papyrus plant, which is traditionally found in the Nile delta of Egypt, yet it thrives here in the waters of Arethusa and Alpheus.

   
   

   Papyrus flourishes in the waters of Arethusa and Alpheus.

   
   

   *Also worth a visit on the mainland of Siracusa are The Greek Theater and the Catacombs.

   *On Ortygia Island, I highly recommend Hotel Domus Mariae. The rooms and bathrooms are spacious, and the balconies, which overhang the ancient sea walls, treat one to views of Mount Etna and the archways leading into Siracusa.
   The breakfasts are delicious, and the staff is efficient and helpful.

8. Taormina – Sicily

   While many towns scatted across the Sicilian landscape are dilapidated and dreary, Taormina sits like a crown jewel atop a cliff overlooking the Ionian Sea. A town that dates back to the 4th century, Taormina is elegant, picturesque, and enchanting. It has long been a favored destination for the rich and famous. Visit in mid-October when the tsunami of visitors that flood the town in high season have headed home.

   
   

   Outside the Archway that leads to The Old Town

   
   

   
   

   View of the Ionian sea from Taormina

   
   

   Stroll through the historic archways that deliver you to Corso Umberto 1, Taormina’s main street, lined with upscale stores. Linger in the town’s intimate piazzas that beckon one to sit at a café nursing a cappuccino or a gelato while soaking up the charm of Taormina.

   
   
   
   

   
   
   
   

   Admire the textured walls, the exposed brick, the natural stone, and the decorative ironwork.

   
   
   
   

   
   
   
   

   Branch off onto the narrow alleys where you’ll come across a choice of cozy atmospheric restaurants and be treated to views of Mount Etna puffing smoke into the blue sky.

   
   
   
   

   
   
   
   

   
   
   
   

   Visit the Greek amphitheater built during the Hellenistic period (3rd century BC) and rebuilt by the Romans in the 2nd century AD. Its unique setting offers gorgeous views of both the sea and Mount Etna.

   
   
   
   

   Taormina has some fabulous beaches. Take the funicular down to the beach at Lido Mazzaro. As you descend, enjoy the bird’s eye view of homes and hotels clustered together on the hillside. Spend the day at Isola Bella, swimming in the calm turquoise waters. Choose a restaurant on the golden sand and relax over a seafood lunch and a glass of white wine.

   
   

   Lido Mazzaro – Isola Bella.

   
   

9. Matera

   Matera is located above the heel of Italy’s boot in the Basilicata region on the border of Puglia. Inhabited for 7,000 years since the Neolithic Age, it is one of the world’s oldest cities. Upon reaching the Old City, one is greeted by the sight of stone houses and ancient cave dwellings – ‘Sassi’ – clinging to each other in a haphazard fashion, which is so utterly charming that for most visitors, it’s a case of love at first sight.

   
   
   
   

   La Citta Sotterranea (the underground city), as Matera is often referred to – overlooks a plateau and a canyon where a river winds and skips over stones.

   
   
   
   

   The most captivating and historic area is Sasso Caveoso, located in the south of Old Town in the vicinity of Piazza San Pietro. Here one comes across rupestrian churches carved into the limestone rock where the original, fading, and peeling Christian artwork that adorned the walls is currently being painstakingly restored.

   
   

   Rupestrian rock-church Santa Maria de Idris.

   
   

   
   

   The rock- church, Santa Maria de Idris, overlooks Piazza San Pietro Caveoso and the canyons.

   
   

   
   

   Faded artwork in Santa Maria de Idris.

   
   

   
   

   Restoration underway in Santa Lucia Alle Malve.

   
   

   A visit to the historic, authentic ‘sasso’ (cave-dwelling), Casa Grotta, gives one a glimpse of how large families lived with their animals in the sassis. Every inch of space was put to use to accommodate hens and their chicks, the family mule, a weaving loom, bread baking, and numerous children.

   
   

   Interior of an ancient cave -house.

   
   

   
   
   
   

   In this part of the city, several sassi have been converted into small boutique hotels and restaurants, all of which retain and respect the authenticity of the caves.

   
   

   A bedroom in a reimagined cave. Hotel La Corte dei Pastori.

   
   

   
   

   A restaurant housed in a rock-cave.

   
   

   Wherever one goes in Matera, one sees quirky and endearing cucù. Cucù are Terracotta whistles in the form of brightly colored roosters and doves, which have been an integral part of festivals and family celebrations for generations. Their bold colors are believed to chase away evil spirits. Cucùs are always placed in homes, restaurants, hotels, etc., facing outward.

   
   

   Hand painted Cucu.

   
   

   Take Via B Buozzi from Piazza San Pietro up the hill to Via D Ridola, where a right turn brings one to a broad, bustling pedestrian street flanked by restaurants and stores. Continue to Piazza Franciso, where little side lanes house boutiques, bars, cafés, and gelaterias.

   
   

   Via D. Ridola a pedestrian street.

   
   

   
   

   Lunch at a Cafe bordering Piazza Sn Francisco.

   
   

   Old Town Matera is a walking city that entices one to randomly explore and lose oneself in the alleys among the stone houses and sassis, where the roof of one dwelling often serves as the foundation of another.

   
   

   
   

   While Old Town is the primary draw for visitors, the new city has its share of majestic Baroque churches and all the conveniences of any modern bustling Italian city.

10. Gallipoli – Puglia

    Located in the South West of Italy’s heel, Old Town Gallipoli – surrounded by defensive walls – is reachable by boat or via a 16th-century limestone bridge, which links it to the mainland.

    
    

    
    

    As one crosses the historic bridge, the imposing Byzantine Castella/Castle comes into view. It boasts four bulky towers – one on each corner – and a fifth tower, Rivello, which stands in the water.

    
    

    
    

    A narrow one-way road loops from the bridge around the island Old Town. Clinging to the edge of the ring road is a sidewalk, which is THE place to stroll and savor the views, especially in the evenings when Italians are out for the habitual ‘passeggiata.’
    Stop in to visit the array of beautiful churches along the route. My favorite is the intimate Santa Maria della Purita with its sumptuous baroque art and floors covered in patterned majolica tiles.

    
    
    
    

    
    
    
    

    As the sun tips towards the horizon, grab a seat at a wine bar and watch the sunset.

    
    

    
    

    
    

    
    

    Visit the early morning harborside fish market just beneath the bridge. Mingle with the fishermen and their customers to witness the animated discussions and negotiations.

    
    

    
    

    Cross the bridge toward the mainland and watch the fisherman preparing, mending, and tending their nets against a backdrop of the harbor, and the castle towers.

    
    

    
    

    Within the defensive walls of Gallipoli, a tangle of alleys and lanes go off in all directions. Lose yourself in the exhilarating maze brimming with life, color, beautiful cathedrals, tiny atmospheric stores, and outdoor restaurants. Explore the picturesque little courtyards that lie beyond ancient archways, now home to boutiques and restaurants.

    
    
    
    

    
    
    
    

    Visit Frontoio del Vicerѐ, an underground oil press. Gallipoli has an abundance of underground oil presses and cisterns, many of them still unexplored.

    
    
    
    

    
    
    
    

    Set aside some time to chill out on Spiaggia della Purita (Beach of Purity) sheltered beneath the imposing defensive walls. It’s a perfect crescent-shaped beach with golden sand that fringes crystal clear calm waters, which are like a massive swimming pool – safe for children, and for swimming enthusiasts, it’s an idyllic, endless, uncrowded swimming pool.

    
    
    
    

    For dinner, choose a restaurant on the edge of the ring road along Riviera Nazario Sauro, and order fresh fish and seafood – particularly the red shrimp unique to Gallipoli.

    The Greeks named Gallipoli – Kallipolis – Beautiful City. Stay awhile, and you too will fall in love.