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 the Southern region of Puglia and near the coast of the Adriatic Sea, visitors who may not be familiar with Alberobello will surely recognize its most distinctive architectural features: the Trulli. A series of small white limestone houses with a pointed roof, upwards of 1,500 Trulli, magically fill the landscape of this wonderful town. Built by peasants and laborers over the centuries, today, these unique landmarks are protected by United Nations Law that 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 the Italian south.
Matera
Matera can trace its history back to prehistoric times, and indeed, as a whole, the town was named a UNESCO World Heritage Site. Situated in the region of Basilicata in Southern Italy, Matera was also named a European Capital of Culture in 2019 by the European Union. Celebrated for its Sassi (ancient cave dwellings), years of dedicated restoration and financial support from the Italian government have transformed this ancient town into a most exciting modern place of discovery. Explore these magnificent stone structures and the now many local businesses, shops, and osterie that reside there including La Lopa Restaurant and its enchanting setting within these stone structures and carved into the hillside. In addition, the Sassi in Miniatura boutique store is a cute destination for some awesome souvenirs. One can even choose to spend a night in a Sassi “hotel” for a most extraordinary 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
Heading back North, the charming village of Manarola forms a part of the beloved collection of five seaside towns known as the Cinque Terre. Situated in the region of Liguria, just under 400 residents call Manarola home, but like its other Cinque Terre counterparts, it sees thousands of tourists visit annually, both domestic and international. A most stunning coastal community, majestic and rugged cliffs pair with the sight of welcoming beaches and the shimmering waters of the Ligurian Sea to form a truly postcard-perfect experience. Go swimming, sunbathing, and sailing, while trying one’s hand at fishing is the ultimate immersive experience. Add cute hilltop homes, scenic hiking trails, and splendid local vineyards like the Cantina Capellini, and it is not difficult to see what makes Manarola and the other Cinque Terre towns such marvelous places of discovery.
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
Beautifully located along the Amalfi Coast of Southern Italy, Positano lies within the Bay of Naples, where there is never a shortage of stunning imagery. Featuring stunning beach areas, hot sun, beautiful blue skies, and an indescribable charm that only a small community can offer, Positano is an absolute delight for all ages. Go swimming, sailing, and even fishing in the pristine waters of the Tyrrhenian Sea while enjoying an authentic Neapolitan-style meal (particularly pizza) creates a real sense of paradise. Try the Ristorante Adamo ed Eva for great seafood and pasta dishes and marvelous vistas, while the Casa Mastro clothing style ensures one can bring home some real Italian style. In addition, such historic landmarks like the Santa Maria Assunta Church, which dates back to the 10th century, are true marvels of human ingenuity against a backdrop of extraordinary natural beauty.
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 imposing Castle of Serravalle that began construction in the 13th century, where in addition to the amazing stone walls and fortifications, truly magnificent views of the town and the sea astound. Meanwhile, Arabic and Phoenician style influences continue to be felt here, and a mosaic of architectural designs and customs can still be found in Bosa. Stroll through the Centro Storico (the historic city core), visit the one thousand year old Chiesa di San Pietro, and learn more about the centuries old tanning process at the fascinating Tannery Museum, there is indeed never a shortage of wonder and beauty to be experienced when in Bosa.
Italy has rightfully earned its status as one of the great cultural, historic, and natural treasures of Europe, and any time spent on this wondrous peninsula will surely create a most special set of memories. Although the major urban and historic centers like Rome, Venice, and Milan will always attract tourism and attention, there is an endless supply of charming and whimsical towns in Italy that are every bit as alluring. From the coastal delights of the Cinque Terre and the Amalfi Coast to the historic beauty of the South and North, there is absolutely never a shortage of wonder to be had when exploring Italy. Come visit this great nation and feel a more intimate side of its people and customs across an exploration of some of these truly exquisite smaller and whimsical towns, always ready to create vacation memories that will definitely last a lifetime.
