5 Overlooked Italian Towns You Should Visit

When most travelers dream about a trip to Italy, their minds go straight to the icons: Rome, Venice, Florence, the Amalfi Coast. And while those places are stunning for a reason, there’s a quieter, more authentic Italy waiting just off the well-trodden path—filled with hilltop villages, coastal gems, and culturally rich cities that haven’t yet been overrun by tourism.

Here are five under-the-radar Italian towns that deserve a spot on your bucket list:

1. Chioggia (Veneto)

A more relaxed, working-class cousin of Venice, Chioggia sits at the southern end of the Venetian lagoon and charms with its colorful buildings, canal-side seafood markets, and lack of crowds. Nicknamed “Little Venice,” this fishing town is actually older than Venice and offers an unpolished beauty that feels real, lived-in, and refreshingly local. Stroll the Corso del Popolo, linger over cicchetti and prosecco at a canal-side bar, and watch fishermen unload their catches in the early morning.

Why go: It’s Venice without the crowds—ideal for seafood lovers, photographers, and anyone craving authenticity.

When to go: You can visit Chioggia on our Fall 2025 Lakes Regions Tour or 2026 Classic Italy Tour. 

2. Trento (Trentino-Alto Adige)

Nestled in the shadow of the Dolomites, Trento is a city of clean lines, Renaissance architecture, and a fascinating mix of Italian and Austrian influence. Its Alpine setting makes it a dream base for hiking and skiing, but Trento itself is well worth exploring: don’t miss the frescoed buildings of the historic center, the impressive Buonconsiglio Castle, or the excellent food scene featuring rich mountain cuisine paired with crisp Trentino wines.

Why go: A sophisticated mountain city with a cultural edge and access to spectacular nature.

When to go: Trento is featured in our Fall 2025 Flavors of Northern Italy and December in the Dolomites tours, or see it in a different season during our 2026 Summer in the Dolomites itinerary!

3. Sorano (Tuscany)

Carved into volcanic tufa cliffs in southern Tuscany, Sorano feels like a town frozen in time. Its winding stone streets, cave dwellings, and ancient Etruscan tombs make it one of the most atmospheric places in the region—yet it’s still overlooked by most Tuscan itineraries. The surrounding area, known as the “tufa triangle,” is dotted with other enchanting towns like Pitigliano and Sovana, not to mention the natural thermal springs of Saturnia, making it perfect for a slow, scenic road trip.

Why go: A mystical, medieval hill town steeped in Etruscan history—and no tourist buses in sight.

When to go: Magical Sorano is one of our destinations for our amazing 2026 Unconventional Tuscany tour.

4. Trapani (Sicily)

Located on Sicily’s western coast, Trapani is a sun-drenched port city with a baroque old town, sweeping sea views, and a gateway to some of the island’s most stunning natural beauty. You’re close to the Egadi Islands, the salt flats of Nubia, winemaking in Marsala, and the mountaintop village of Erice. Trapani also has a strong culinary identity rooted in Arab and Mediterranean traditions—think couscous with fish, pistachio pesto, and sweet almond pastries.

Why go: A Sicilian port city with a rich mix of culture, cuisine, and access to hidden coastal treasures.

When to go: Trapani is featured on our 2026 Wonders of Western Sicily itinerary.

5. Perugia (Umbria) 

Often overshadowed by its flashy Tuscan neighbors, Perugia is the historic and cultural heart of Umbria—and a dream for travelers who want medieval streets, fewer crowds, and all things Truffle! Home to one of Italy’s oldest universities, Perugia has a lively, youthful energy alongside its ancient soul. Visit during one of their many festivals —or simply spend your days sipping wine on sun-drenched piazzas and exploring the city’s underground Etruscan ruins.

Why go: A vibrant hilltop city with deep roots, world-class food, and a refreshingly local vibe.

When to go: Perugia in the springtime is lovely! Visit with us during the 2026 Classic Italy Tour.

Travel Deeper, Go Slower

The joy of traveling in Italy lies not just in the famous sights, but in the moments of discovery—in towns where life moves a little slower, where locals still greet you on the street, and where the food tastes like someone’s grandmother made it just for you. So the next time you plan a trip to Italy, let us take the reigns and curate the most magical itinerary, where we leave space for the unexpected. You might just fall in love with a place you’d never heard of before.

Have questions about these or any of our other destinations? Contact us - we'd love to set up a call to chat!