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BlogTravel tips7 amazing small towns in Italy to plan your next trip around
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Travel tips

7 amazing small towns in Italy to plan your next trip around

Sep 30, 2022 by The Go Ahead Tours Team

For many travelers, Italy is the ultimate bucket list destination—and we totally get it! Who can deny its alluring mix of history, food, architecture, landscapes, and shopping? The country has so much to offer that many travelers book multiple tours to Italy. If you’ve already checked popular spots such as Rome, Venice, Florence, and the Amalfi Coast off of your list, it might be time to start exploring some of the best small towns in Italy. What they lack in acreage and international popularity they more than make up for in outsized charm, culinary heritage, and natural beauty.

Towns in Italy come in countless forms—each as exciting and as beautiful as the next. One might be a hilltop fortress, or an art lover’s dream, or a historic enclave, or a seaside retreat. Some might be right outside the big cities while others are tucked away in the countryside of Italy. That’s why we love the idea of planning your next trip around these seven amazing small towns in Italy; you never know which under-the-radar Italian characteristics they’ll reveal to you.

Find tranquility and history in these countryside towns

A reflecting pool, filled with green water, within the manicured gardens of Villa d'Este with the villa visible in the background.

1. Tivoli

Our weeklong Rome: The City Experience tour comes with two free days—perfect for exploring the small Italian towns surrounding the city. One that's super easy to reach is Tivoli. Located just 16 miles east of Rome, Tivoli is one of the most beautiful small towns in Italy thanks to two World Heritage Sites that call it home.

There’s Villa d’Este, a stunning Renaissance villa surrounded by steep, staggered gardens. Then there’s the jaw-dropping Villa Adriana, a 120-hectare country escape that Emperor Hadrian built around 118 A.D. Note that only 40 of those acres are open to the public today, but the collection of imposing ruins living under the canopy of pine trees is as impressive as any ancient site you’ll find when you explore this destination on our Italy tours.

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Related article: The Beginner’s Travel Guide to Rome →


beige colored buildings decorated with medieval flags in the Arezzo, Italy's Piazza Grande

2. Arezzo

Whether you’re on our nine-day A Week in Italy: Venice, Florence & Rome tour or the Florence, Tuscany & the Italian Riviera tour you’ll get a free day in Florence. If you’re eager to explore beyond the city's walls, strike out for the Italian town of Arezzo in eastern Tuscany. The stunning hometown of Italian filmmaker Roberto Benigni, Arezzo was the backdrop for the Oscar-winning movie Life is Beautiful.

Beyond its Hollywood bona fides, what makes Arezzo one of the best towns in Italy is its expertly preserved historic features. Arezzo is known for its striking medieval architecture and the gorgeous Piero della Francesca murals hidden within various churches, including the Arezzo Cathedral, which also displays a sculpture by Donatello. Don’t miss the chance to discover this town on our Florence tours. If your trip takes place on a Sunday, be sure to check out the shopping and people-watching at the weekly antiques market on piazza grande.

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Related article: 6 unique experiences to have in Florence that go beyond an Italian guidebook →


the sun shining on the Arch of Trajan, decorated with reliefs and scripture

3. Benevento

Located about 30 miles east of Naples, on a hill in the countryside of Italy, Benevento makes an appearance in both our Food & Wine: Campania, Puglia & the Amalfi Coast tour and our Puglia & Southern Italy tour. That’s because small towns in Italy don’t get more historic than this one. Benevento offers a trove of ancient treasures: There’s the 9th-century Benevento castle, the Roman theater that Hadrian built, the fantastically preserved Trajan Arch from 114 A.D., and Santa Sofia Church, which was declared a UNESCO World Heritage Site in 2011.

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Related article: The best things to do, eat, and see in Southern Italy → 


Revel in la dolce vita in these coastal towns

travelers walking over decorative tiles towards a ledge, looking out over the coast line

4. Taormina

In recent years, travel to Sicily has skyrocketed. It’s not at all surprising; this historic island is dotted with some of the best small towns in Italy—including Taormina. Taormina is home to just about 11,000 people and is staggeringly beautiful, which is why it features in so many of our Italian itineraries, including our nine-day A Week in Sicily: Palermo, Syracuse & Taormina tour.

If you really want to dig into all that one of the best coastal towns in Italy has to offer, our 12-day Sicily: A Cultural Journey tour lets you add two additional days in Taormina. You’ll get to marvel at the medieval details of the Taormina Cathedral, the 14th-century opulence of Palazzo Corvaja (seat of the first Sicilian parliament), and the enduring, sea-facing majesty of a 2nd-century Greek amphitheater. Plus, you’ll get to experience all of this with snow-capped Mount Etna providing the perfect backdrop.

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Related article: 4 ways to spend free time in Taormina →


a women, sitting in a small red boat, gazing at boats floating in the blue water near a stone wall

5. Ischia

In addition to seeing the rugged cliffs of Positano and tasting the delicious flavors of Naples, one of the best features of our nine-day Amalfi Coast Walking Tour is the number of free days for a more personalized experience. Our Tour Directors can help set you up with guided hikes, farm visits, and much more, but we also offer a guided excursion to Ischia, a verdant, volcanic island in the Gulf of Naples.

It may not be the most popular island in Italy, but Ischia will surprise you with lush landscapes, bustling beaches, stunning vineyards, and rich history. You can relax at a hot-spring resort, explore a medieval castle, or even visit an 18th-century palazzo that now houses the Sea Museum, a showcase for Ischia’s fishing industry. It’s an island for every type of traveler.

Check out Ischia tours

Related article: 16 of the best islands to visit in the world (that you won’t find on every travel list) → 


Discover the flavors of Italy’s foodie towns


a road, lined with street lamps, winding around white and beige-colored houses at golden hour

6. Ostuni

Located in the heart of Puglia, Ostuni offers the best of many worlds as far as charming Italian towns go. It’s just minutes away from the beach, making it one of the best small coastal towns in Italy. It’s also a picturesque hilltop town, painted in shades of white, blue, and green thanks to the white-washed architecture, the endless sky, and the atmospheric olive groves that snake around it.

On our brand-new, 12-day Food & Wine: Campania, Puglia & the Amalfi Coast tour, you’ll discover that Ostuni is also one of the best small towns in Italy for food when you tuck into an olive oil and wine tasting. Plus, don’t forget the panzerotti, which is fried bread stuffed with mozzarella and tomato. It’s a local delicacy—and a can't-miss.

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Related article: Booking a summer trip? Here are 7 unique places to travel that are popular for Europeans →


a table covered with pizzas, water glasses, and Aperol spritz

7. Orvieto

What makes this historic Umbrian hamlet one of the best small towns in Italy? We love how it dramatically rises up from the rugged cliffs of an ancient volcanic tuff. This picture-perfect geography is one of its most unique features, but they don’t stop there.

Originally founded by the Etruscans in the 9th century B.C. and then taken over by Romans in the 3rd century B.C., this Italian town of 20,000 inhabitants is chock-full of history. It’s also one of the stops on our Food & Wine: Flavors of Tuscany & Umbria tour, during which you’ll want to keep your eyes peeled for traditional fare, including slow-cooked pigeon and lumachelle, a snail-shaped bread roll that can be served cold, hot, sweet, or savory.

Plus, on our 12-day Venice, Florence & Rome tour, you’ll actually get to take a funicular up to Orvieto for some incredible views of the Umbrian countryside.

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Which small towns in Italy are you dreaming of visiting? Let us know on our Facebook page and get inspired by our Italy tours.


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About the author | The Go Ahead Tours Team
We’re a team of passionate travel experts, dedicated to helping people explore the world. From inspiring stories to tips for an amazing trip, the topics we cover are all about getting you out there and making discoveries.

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