7 Whimsical Towns In Italy
A veritable jewel of Western Europe, Italy is beloved across the world for its stunning natural landscapes, its status as a capital of art, literature, and cuisine, and its fascinating centuries of history. Indeed, it is not difficult to see why the Italian Peninsula remains one of Europe’s most popular destinations, and any guests who visit can expect a varied and diverse experience from the North to the South. From the peaks of the Alps to the Mediterranean Sea, Italy’s splendid charm never disappoints. While major cities like Rome, Naples, Florence, and Milan still attract the most attention, there are a number of small towns across the nation that are as equally captivating as the major urban centers. So when visiting the “Bel Paese,” add these whimsical towns to the itinerary, for a truly rounded view of the beauty that is Italy.
Cortina D’Ampezzo
Situated in the heart of the Dolomite Mountains in Northern Italy’s Veneto region, the beautiful Cortina d’Ampezzo is a true outdoor delight. Home of the 1956 Winter Olympics and the upcoming 2026 edition, winter sports lovers traveling in this part of the country will surely not want to miss out on Cortina. Known for its fine alpine resorts, amateurs and professionals alike have long enjoyed the challenging ski, snowboarding, and sledding slopes of this Italian gem.
Home to a modest population of just under 6,000 inhabitants, in addition to the sports activities, the scenery in Cortina is absolutely stunning. With an abundance of splendid Mountain vistas, charming chalet houses, and, of course, loads of inviting eateries and cafes, visiting Cortina d’Ampezzo is like stepping into a master artist’s painting. Amongst the stops of note include the delicious Il Vizietto di Cortina restaurant for some of the best of Northern Italian cuisine and the Cathedral of the Madonna della Difesa, which highlights the peak of Italian Baroque art.
Alberobello
Founded in the 16th century, the uniquely charming town of Alberobello is surprisingly one of Italy’s youngest places. Situated in southern Puglia, near the Adriatic coast, visitors unfamiliar with Alberobello will surely recognize its most distinctive architectural features: the Trulli. A series of small white limestone houses with pointed roofs, the Trulli, numbering more than 1,500, magically fill the landscape of this wonderful town. Built by peasants and laborers over the centuries, these unique landmarks are protected under United Nations law, which declared them a World Heritage Site in 1996. Add in warm sea breezes, hot sun, and plenty of inspiring panoramas, and Alberobello stands as one of the most uniquely beautiful places in southern Italy.
Matera
Matera's history dates back to prehistoric times, and the entire town has been designated a UNESCO World Heritage Site. Located in Basilicata, Southern Italy, Matera was also named a European Capital of Culture in 2019 by the European Union. Famed for its Sassi (ancient cave dwellings), years of restoration and support from the Italian government have transformed this historic town into an exciting modern destination. Visitors can explore these stunning stone structures and enjoy the many local businesses, shops, and osterie, including La Lopa Restaurant, which is beautifully set within the stone formations and carved into the hillside. The Sassi in Miniatura boutique offers charming souvenirs, and you can even spend a night in a Sassi hotel for a truly unique experience.
A frequent destination for film crews, among the famed movies that were partially shot in Matera include Wonder Woman (2017) and The Passion of the Christ (2004).
Manarola
Traveling north, the charming village of Manarola is part of the renowned five seaside towns called the Cinque Terre. Located in Liguria, it has fewer than 400 residents, yet like its neighboring towns, it attracts thousands of visitors each year, both local and international. This breathtaking coastal village features dramatic cliffs alongside welcoming beaches and the shimmering Ligurian Sea, creating an idyllic postcard scene. Visitors can enjoy swimming, sunbathing, sailing, and fishing for an authentic experience. With charming hilltop houses, scenic hiking trails, and beautiful local vineyards such as Cantina Capellini, it's easy to see why Manarola and the Cinque Terre towns are such captivating destinations.
Mantova
A place steeped in history, the Medieval and Renaissance town of Mantova is a true wonder that is regretfully overlooked by many traveling Northern Italy. Situated some two hours from the city of Milano, Mantova is a culturally rich destination that offers some of the very best of what makes Italy a true European treasure. Named the European Capital of Culture in 2016 by the European Union and a UNESCO World Heritage Site in 2008, guests can expect a dizzying array of centuries old churches, buildings, towers, and piazzas (town squares), that transport one to the turbulent years of the Middle Ages and beyond. Amongst the landmarks of note include the Church of San Francesco (1304), the Castello di San Giorgio, built in the early 15th century, the Palazzo Te (1534), and the Palazzo Ducale which began construction in the 14th century. Add in a surrounding wetland, and the special allure of this town is hard to beat.
For art and music lovers, Mantova may be familiar as the setting for Giuseppe Verdi’s opera Rigoletto (1851), while admiring such artistic masterpieces from the likes of Rubens and Raphael is like a heavenly delight.
Positano
Perched along the Amalfi Coast of Southern Italy, Positano is within the Bay of Naples, offering endless breathtaking views. With its beautiful beaches, warm sunshine, clear blue skies, and a charm exclusive to small towns, Positano is a perfect destination for all ages. Visitors can swim, sail, and fish in the pristine Tyrrhenian Sea while enjoying authentic Neapolitan dishes, especially pizza, creating a sense of paradise. Dining at Ristorante Adamo ed Eva provides excellent seafood, pasta, and stunning vistas, and shopping at Casa Mastro allows visitors to take home authentic Italian style. Additionally, historic sites like the 10th-century Santa Maria Assunta Church are marvels of human craftsmanship set against extraordinary natural scenery.
Bosa
Bosa is picturesquely located on the island region of Sardegna, where a stunning Mediterranean ambiance always pleases. Known for its brightly colored pastel-painted houses, just over 8,000 residents call this most delightful town home. As a fishing community along the Temo River, the sights, sounds, and smells of this ancient profession fill the landscape, offering visitors the opportunity to truly experience the daily goings-on of a fisherman. Enjoy authentic seafood restaurants like Il Tipico and Sa Nassa, where the chance to try tasty Sardinian cuisine is a mouth-watering proposition. Meanwhile, Bosa's historic character is also a defining feature of this inviting town, and centuries-old architecture can be admired here.
Visit the impressive Castle of Serravalle, built in the 13th century, where stunning stone walls and fortifications offer breathtaking views of the town and the sea. The area still reflects Arabic and Phoenician influences, showcasing a rich blend of architectural styles and customs in Bosa. Walk through the Centro Storico, explore the thousand-year-old Chiesa di San Pietro, and discover the centuries-old tanning process at the Tannery Museum. Bosa is always full of awe-inspiring sights and beauty.
Italy rightly stands as one of Europe's greatest cultural, historic, and natural treasures. Time spent on this beautiful peninsula is bound to create memorable experiences. While major cities like Rome, Venice, and Milan draw crowds, Italy's charming smaller towns are equally captivating. From the scenic coastlines of Cinque Terre and the Amalfi Coast to the historic splendor of the North and South, there's always something amazing to discover. Visiting Italy offers a chance to experience its authentic charm, customs, and the warmth of its people through its quaint, whimsical towns. These destinations promise vacation memories that will last a lifetime.
