10 Best Small Towns in Italy for a Weekend Retreat
Italy is celebrated for its timeless beauty, rich culture, and tasty culinary delights. When most people think of where to visit in Italy, some of the more common locations that come to mind include Rome, Venice, and Capri. However, venturing into less populated regions can offer many incredible sights and activities without all of the chaos and crowds. There is no limit to the natural beauty of Italy, and you can explore its hidden gems in these ten best small towns in Italy for a weekend retreat.
Porto Venere, Liguria
Porto Venere is a hidden gem compared to the busier Cinque Terre, tucked away on the Ligurian coast. Known as the smallest seaside village in the province of La Spezia, it’s an ideal escape for those wanting fewer crowds but equally stunning views. The town’s picturesque appeal has earned it the title of a UNESCO World Heritage Site, with panoramic vistas over the Gulf of La Spezia (the Bay of Poets). The 14th-century Castello Doria, the Porta del Borgo city gate, and Lord Byron’s Grotto are all sights you do not want to miss on a weekend trip to Porto Venere. For luxurious accommodation along the Ligurian coast, consider staying at the seafront Grand Hotel Portovenere, a 17th-century monastery just a quick walk from the town center.
Treia, Marche
For a quiet getaway steeped in history, Treia is a must-visit small town in Italy. Located less than 20 kilometers from Macerata, the town offers expansive views from the Adriatic Sea to the Sibillini Mountains. Explore the 12th-century San Marco Tower, the Teatro Comunale, and the 450-year-old Roverella Oak. Embrace the sports of the past with the annual Disfidia in July, where the town plays Il Gioco della Palla col Bracciala, meaning the game of the bracelet ball. Treia’s peaceful atmosphere makes it an ideal spot to unwind and soak up Italy’s serene countryside. Hotel Grimaldi is located in the historic center of Treia, with accommodations set in a landmark building that is perfect for a weekend trip.
Anghiari, Tuscany
Perched on a hilltop in Tuscany, Anghirari is one of Italy’s most beautiful medieval towns. Surrounded by ancient walls, the town is known for its artisans specializing in woodwork, textiles, and ceramics. History lovers will appreciate the Museo della Battaglia di Anghiari, commemorating a famous battle depicted by Leonardo da Vinci. Take time to explore the town’s charming streets, palaces, and churches like Santo Stefano and Sant’Agostino. This gorgeous town borders the Umbria, Marche, and Romagna territories. Less than a mile from downtown is Il Cardo Resort, a 15th-century farmhouse transformed into an idealistic resort for extended stays in the Tuscan countryside.
Brisighella, Emilia-Romagna
Famed for its olive oil and medieval landmarks, Brisighella is a tranquil village surrounded by rolling hills. The town’s main attraction, La Rocca Manfrediana, is a 14th-century fortress offering panoramic views. Do not miss out on the infamous Clock Tower, Monticino Sanctuary, or the winding Via Degli Asini (the Donkey Street). The nearby Vena del Gesso Regional Park, with more than 200 caves, is perfect for nature lovers looking for a peaceful retreat. For day trip options, Florence is only a 2-hour drive away. For a weekend trip in Beisighella, consider staying at Villa Liverzano. Less than two miles outside the city center, the villa offers peace and tranquility with a garden, swimming pool, spa & wellness center.
San Vito Lo Capo, Sicily
If you’re looking for coastal beauty, San Vito Lo Capo in Sicily is a paradise for beach lovers. Originating as an ancient Roman port, the northwest tip of Sicily is renowned for its beaches and mountain backdrops. The town’s clear waters and golden sands have earned it the Blue Flag award for its standards of cleanliness. Adventure seekers can enjoy rock climbing on coastal cliffs, while nature enthusiasts can explore the untouched trails of the Zingaro Nature Reserve. San Vito’s festivals, clean beaches, and stunning scenery make it a top Italian weekend destination. Il Faro E La Luna Beach Apartments are a great option for accommodation, featuring a hot tub and just a minute's walk to San Vito Lo Capo Beach.
Orvieto, Umbria
Sitting atop a volcanic rock, Orvieto blends history and breathtaking landscapes. Its impressive Duomo di Orvieto is a stunning Gothic cathedral known for its dramatic design. Visitors can explore the town’s underground tunnels, carved into volcanic stone. Umbria was the birthplace of St. Benedict and Francis of Assisi, giving the region a creative and mystical energy. The Torre del Morro offers panoramic countryside views, while the old town’s narrow lanes invite you to step back in time. Set in between Florence and Rome, Orvieto is a great option for a weekend trip. La Magnolia is accommodation set in a historic building less than 500 feet from the cathedral that offers free bike rentals during your stay.
Matera, Basilicata
The southern region of Basilicata is home to the rocky city of Matera. Matera is one of the world’s oldest continuously inhabited cities, famous for its ancient cave dwellings. A UNESCO World Heritage Site, the Sassi di Matera features a network of caves once used as homes and churches. This unique small town holds evidence of human settlement from as early as Paleolithic times to today. Visitors can tour Casa Grotta di Vico Solitario or explore the Parco della Murgia Materana, which offers scenic hiking paths. Matera’s rich history and unique geography make it a must-visit for an extended weekend stay. Palazzo Degli Abati provides accommodation within the Matera Stassi area, where you can choose one of their unique rooms carved out of rock.
Cefalu, Sicily
The coastal town of Cefalu is known for its Mediterranean charm and striking Norman cathedral, featuring Byzantine mosaics and stunning ocean views that make it a UNESCO-listed destination. Cefalu brings history and beach relaxation, its picturesque Spiaggia di Cefalu, and winding medieval streets. The small town is also a popular base for hiking, and film buffs may find intrigue in Cefalu’s recognition from the Italian classic Cinema Paradiso. The Madonie National Park and Palermo are nearby destinations worth driving to. Taliammari is a hotel located in the Old Town district with beachfront access and shuttle services available for extended trips.
Alberobello, Puglia
Alberobello is famous for its unique trulli houses, which are known as UNESCO World Heritage Sites. These limestone dwellings, built without mortar, create an atmosphere that feels out of a fairytale. A walk through Rione Monti and Rione Aia Piccola showcases the town’s ancient architecture. Popular activities include walking tours and exploring the Trullo Sovrano, the only two-story trullo. The trulli houses are considered one of Europe's best vernacular architectural examples. If you're looking to stay in a traditional Trulli building, Trulli Holiday Albergo Diffuso offers accommodation around the center of Alberobello.
Cortona, Tuscany
Perched on a hill with panoramic views over the Val di Chiana, Cortona is a town rich in Etruscan history. Located 30 km south of Arezzo, Cortona is one of the many hill towns in Tuscany. While spending a weekend in Cortona, Key sights include the Basilica of Saint Margaret, the Academia Etrusca, and the charming Piazza della Repubblica. Views of the Lago di Trasimeno, the fourth largest lake in Italy, can be viewed from Cortona’s public gardens. The historic roots and stunning landscape make this small town an ideal weekend retreat destination. Dolce Maria is a medieval hotel just a stone's throw away from Piazza della Repubblica, featuring elegant rooms.
These ten small towns across Italy combine history, gorgeous landscapes, and cultural landmarks perfectly. A weekend spent in any Italian city will be an unforgettable experience. However, these smaller, more obscure towns give you the space and peace to explore at your leisure. Whether exploring ancient caves, strolling through medieval streets, or taking in coastal views, any of the ten destinations listed above offer a weekend getaway guaranteed to make a memorable Italian vacation.
