Getting lost in the mazy streets of a tucked-away hill town is one of the true delights of travel in Italy. Here you’ll wander cobbled streets lined with shuttered houses, turning a corner to find a majestic piazza or wonderful family-run trattoria. But don’t limit yourself to the best-known towns—read on for six of our hidden favorites.
## Montalcino: A Tuscan Dreamscape Unveiled
Tuscan hill towns are celebrated far and wide, and their allure is undoubtedly well-deserved. However, to truly experience the magic of the Tuscan countryside, venture beyond the familiar paths of Siena and San Gimignano and discover the enchanting medieval walled hill town of Montalcino. Poised majestically high above the breathtaking Val d’Orcia, Montalcino offers a unique perspective on the beauty of Tuscany. From its elevated vantage point, the town gazes out over a tapestry of verdant vineyards, the very source of its renowned Brunello red wines. These exceptional wines, celebrated for their rich character and exquisite flavor, can be sampled and savored at numerous local establishments within the town’s ancient walls.
From the imposing ramparts of Montalcino’s 14th-century fortress, known as the Rocca, an unparalleled panorama of Tuscan scenery unfolds before your very eyes. The vista stretches across a landscape of golden cornfields, silvery olive groves, and rolling hills that gently dip and rise towards the distant mountains of the Maremma. This breathtaking view is a feast for the senses, a reminder of the timeless beauty that defines the Tuscan countryside. Immerse yourself in the local culture by indulging in the full-bodied, robust wines at a traditional enoteca, where you can sample the flavors that have made Montalcino famous. Find a comfortable spot at a charming cafe on the historic Gothic Piazza del Popolo, the heart of Montalcino, and soak in the atmosphere of this vibrant town. For a dose of art and history, explore the Museum of Sacred Art, which houses a remarkable collection of Sienese paintings and sculptures, offering a glimpse into the region’s rich artistic heritage.
When hunger calls, make your way to the rustic charm of Locanda Demetra, a delightful establishment located just south of Montalcino. Here, you can experience the true taste of Tuscany with a farm-to-plate lunch, featuring fresh, locally sourced ingredients prepared with traditional recipes. The restaurant’s commitment to using seasonal produce ensures an authentic culinary experience that will tantalize your taste buds. As evening approaches, Montalcino offers a wealth of atmospheric accommodations to suit every taste and budget. For a truly luxurious experience, consider a stay at the Castello Banfi estate, spectacularly centered on a magnificent medieval castle that overlooks the sprawling vineyards. This unforgettable setting provides a glimpse into the region’s rich history and offers a truly immersive experience.
To truly appreciate Montalcino at its most serene and peaceful, plan your visit for the early morning hours or the tranquil evening. Alternatively, consider visiting during the spring or autumn months, when the crowds are thinner and the weather is mild. During the summer, Montalcino comes alive with the popular Jazz and Wine Festival, a vibrant celebration of music and wine that attracts visitors from around the world. While the festival is a fantastic experience, it can also bring larger crowds to the town.
## Urbino: A Renaissance Jewel in Le Marche
Often overshadowed by the fame of Tuscany, the central Italian region of Le Marche remains a blissfully underrated destination. Within this hidden gem lies the captivating university town of Urbino, a secret too precious to keep to ourselves. This is the birthplace and childhood home of Renaissance superstar Raphael, a place that undoubtedly served as a profound source of inspiration for the artist. The travertine domes and towers of Urbino’s walled historic center stand as a testament to the town’s architectural splendor and artistic heritage. Cultured, erudite, and undeniably pleasing to the eye, Urbino is a true Renaissance jewel, a fact recognized by its designation as a UNESCO World Heritage site.
If ever proof were needed that world-class art can be found in Italy beyond the major cities, Urbino is a compelling example. The town’s pride and joy is the magnificent 15th-century Palazzo Ducale, a masterpiece of Renaissance architecture. With its elegant arcaded courtyard and unparalleled collection of Renaissance art, the Palazzo Ducale is a must-see for any art lover. Within the Galleria Nazionale delle Marche, housed within the Palazzo Ducale, hang masterpieces by renowned artists such as Raphael, Piero della Francesca, and Titian, offering a glimpse into the artistic genius of the Renaissance. At the Casa Natale di Raffaello, the house where Raphael was born in 1483, visitors can admire one of his earliest frescoes, the delicate and charming “Madonna and Child.” This intimate setting provides a personal connection to the artist and his early life.
For a sweet, simple, and centrally located place to stay the night, consider Albergo Italia, a charming hotel that offers comfortable accommodations and a warm, welcoming atmosphere. And don’t leave Urbino without experiencing the season-driven home cooking at Antica Osteria da la Stella, the very inn where Raphael himself once lodged. This historic establishment offers a taste of traditional Le Marche cuisine, prepared with fresh, local ingredients.
## Spello: A Floral Tapestry in Umbria
Spello, nestled in the Perugia province of Umbria, is a quintessential hill town beauty that manages to remain relatively uncrowded, even during the peak tourist season. With its majestic towers and elegant campaniles rising above a charming collection of higgledy-piggledy houses constructed from honey-colored stone, Spello embodies the quintessential Italian dream. Its ancient cobbled lanes, worn smooth by centuries of foot traffic, are adorned with vibrant flower boxes and hanging baskets during the summer months, creating a tapestry of color and fragrance that enchants visitors.
A visit to the Baglioni Chapel at Chiesa di Santa Maria Maggiore is an absolute must, where you can marvel at the breathtaking Pinturicchio frescoes, masterpieces of Renaissance art that depict scenes from the life of the Virgin Mary. Take a leisurely walk up to the Roman arch at the highest point of the town for breathtaking panoramic views of the surrounding hills and plains. Afterwards, indulge in a sublime lunch at Osteria del Buchetto, where you can savor traditional Umbrian cuisine while enjoying the stunning scenery. To truly immerse yourself in the romance and tranquility of this enchanting hill town, consider an overnight stay at Agriturismo Il Bastione, a medieval farmstead surrounded by lush olive groves, or Palazzo Bocci, a magnificent 17th-century palace located in the heart of the historic center. Both options offer a unique and unforgettable experience, allowing you to connect with the history and beauty of Spello.
## Asolo: The Pearl of the Veneto
Oh, the views! Nestled in the picturesque foothills of the Dolomites and just 50 miles north of Venice, Asolo is a delightful and easily accessible destination. Its breathtaking backdrop, with its imposing ramparts offering grandstand views of the surrounding wooded hills and majestic mountains, makes Asolo a true visual delight.
Capped by a medieval fortress, this charming hill town boasts lanes lined with houses painted in vibrant fresco colors. The town’s 18th-century cathedral houses an altarpiece by Venetian Renaissance master Lorenzo Lotto, a testament to Asolo’s rich artistic heritage. On the second Sunday of each month, Asolo transforms into a bustling antique market, attracting collectors and enthusiasts from far and wide. From Asolo, you can easily plan a day trip to explore the vineyards of Veneto’s renowned Prosecco region, indulging in the sparkling wines that have made the area famous.
Located right on the main piazza, the five-star Albergo al Sole provides a romantic and luxurious base for exploring Asolo. For a memorable dinner, secure a table at the family-run Locanda Baggio, located on the outskirts of town. Here, you can savor dishes prepared with locally sourced meats and fresh seafood, experiencing the authentic flavors of the Veneto region.
## Erice: A Sicilian Fortress in the Sky
Clinging to the slopes of 2460-foot Mount Eryx, Erice offers breathtaking views over the countryside and coastline of northern Sicily, stretching all the way to Tunisia on clear, cloud-free days. This is arguably the most quintessential hill town in Italy, with its charming cobbled alleys winding their way up to breathtaking viewpoints, ancient medieval churches, and quaint little piazzas where the rhythm of daily life unfolds.
Despite its proximity to the port town of Trapani, Erice feels like a world apart, a place where time seems to slow down and the beauty of Sicily is amplified. The town’s crowning glory is the majestic Castello di Venere, where the Romans once worshipped the love goddess Venus. A walk along the castle ramparts offers unparalleled views, providing an unforgettable experience. While in Erice, be sure to sample the town’s famous almond dolci (sweets), based on the time-honored recipes of local nuns. These delectable treats are a testament to Erice’s culinary traditions. For a peaceful and spiritual retreat, consider a stay at Il Carmine, a tranquil hotel housed in a former Carmelite monastery.
## Maratea: A Basilicata Jewel on the Coast
With its lushly wooded mountains, the bluest of seas, and dramatic soaring cliff faces, Maratea is a scenically stunning destination. Located just above the toe of Italy’s boot, this get-away-from-it-all village boasts the same winding roads and breathtaking sea views as the Amalfi Coast further north, but with only a fraction of the crowds.
Once a favorite among celebrities like Frank Sinatra and Princess Diana, Maratea has a charm that captivates all who visit. Explore the historic center, adorned with 44 churches and candy-colored houses that cascade down towards the sea far below. Maratea’s most prominent landmark is reminiscent of Rio de Janeiro: a statue of Christ the Redeemer with arms outstretched, offering a blessing over the town. Climb up and above the town to explore the ruins of the original Greek settlement, where you can enjoy more breathtaking panoramic views.
Locanda delle Donne Monache, a chic boutique hotel housed in a converted 18th-century monastery, provides a wonderful escape, offering quiet gardens and a refreshing pool. This tranquil setting is the perfect place to relax and unwind, allowing you to fully appreciate the beauty and serenity of Maratea.
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