The Most Charming Small Towns in Italy

Curate a vacation that speaks to the soul by visiting these charming small towns in Italy.

Rome, Milan, Venice…they’re all wonderful destinations just vying for a visit, but these cities are far from the only Italian locales you should keep your eyes on. With so many beautiful small towns dappling the Italian landscape, it only makes sense you’d want to see a few of them during your trip.

Here are the most charming small towns in Italy, just for you.


With a year-round population of just 416, coastal Portofino has it all. Small town vibes accentuate otherworldly beauty. Sail into the port from other European destinations or arrive by roadway. Whatever you choose, make the most of Riviera glam without all the noise. Sparkling wine, hand-spun pasta, designer boutiques for one-of-a-kind shopping…our kind of vacation! With its own peninsula and a close proximity to Genoa, Portofino is sprezzatura encapsulated.


From first glance, Alberobello is a unique town. Nestled in Puglia, it’s known for trulli, or conical-roofed dry stone architecture. With so many of these bungalow-esque homes freckling the village, Alberobello became a UNESCO World Heritage Site (as it has remained for 24 years). Bright greenery contrasts the white buildings for a feeling of artistry as you walk through the cobbled ways. For the best views in town, make your way toward the Belvedere Santa Lucia (and bring your camera).


Catch a train from Rome and you’ll be at Sperlonga within an hour. Beaches, greenery and culture abound here. Visit the Museo Archeologico di Sperlonga, which gives you a genuine account of the area’s ancient ruins. In fact, it’s located right among the former villa of Emporer Tiberius, who reigned from 14-37 AD. It’s a truly gorgeous place that oozes history while still offering contemporary fun.


Surely you’re familiar with Tuscany, if only through pictures. Within the region, Collodi is a hillside escape between Florence and Pisa, and it has some real medieval aesthetic. Strike a pose beside the world’s tallest wooden Pinocchio statue at Pinocchio Park, and leisurely peruse through the Bonsai Museum and Butterfly House. While its history may be troubled, Collodi reaps the benefits of Italian spirit through handmade fare and charming activities.


A super remote destination, Castellucio houses just a few residents. Its charm includes a steep ascendance (5,000 feet above sea level) and a panoramic view of the Apennine Mountain Range. Despite the fact that an earthquake hit in 2016, some locals have rebuilt their shops & restaurants for visitors. Fields of colorful flowers bloom each year. Nothing compares to this magical, quaint Umbria town.


The world is no stranger to the Amalfi Coast, but within this region lies a hidden escape you just have to see. Up atop one heck of a winding road, you’ll find the textured coast of Ravello. The town itself is most known for Villa Rufolo and Villa Cimbrone, two places that are as chic as they are removed. The Duomo is a cathedral that dates all the way back to the 11th century—enter the bronze door and discover the blood of St. Pantaleon himself. Visit on July 27th, the anniversary of his death, and you may even see it mysteriously transform into liquid.


This time, we’re going to the alps. Merano, where tropical niceties couple with alpine tendencies, is a climate fusion. The landscape includes fruitful gardens, castle ruins and snowy hills. Most of the year, this town is a sunny escape. No matter the season, Terme Merano (one of the most luxurious spas in all of Europe) makes for the ideal atmosphere. Let’s not forget about the vineyards, and the buon vino that comes from it.


Ever seen Under the Tuscan Sun? This is the setting for both the novel and film. You’ll find a handful of Michelin-star restaurants here, including Osteria Del Teatro, a theater-forward dining affair. Cortona wine tours take you to Baracchi Winery, Avignonesi Winery Fattoria Le Capezzine and more. The Fortress of Girifalco takes you all the way back to 16th century Italy. Whatever you do, you have to catch the Museo Diocesano, which includes the work of Cortona-born Luca Signorelli and Pietro da Cortona and local Fra’ Angelico.


Just a couple thousand people live in Pienza, but travelers love to visit. Stone streets and buildings bring a cozy feel to every alley. Grab a cocktail at Idyllium come evening time and visit the Duomo by day. Take your pick of charming, pristine and inviting accommodation. From the town itself, you can actually see the breathtaking image of Val d’Orcia, a place of rolling hills and plenty of magic.

Orta San Giulio

If you find yourself in Milan (which you should), take the quick trip to Orto San Giulio. Just over an hour from the city by car or train, the town has a front row view of beautiful Lake Orto. Wisteria flowers decorate the streets, many of which are crafted from cobblestone. And those hills in the distance—they grow truffle mushrooms. We can taste them now. You can actually take a ferry to an island within the lake, called Isola San Giulio. The island is less than a thousand feet in length, but it manages to house a basilica, a peaceful walkway that goes about the island’s circumference and colorful frescoes that are a sight to be seen.

An Authentic Italian Getaway

If you’re after something a little more authentic than any city can provide, heading to a charming small town or two is the way to go. It gives you the chance to tune into genuine culture, and maybe even make some long-lasting connections. These scenic villages have it all: narrow cobblestone streets, medieval architecture and colorful flowers climbing the stone walls of these picturesque cities. Italy has a number of stunning towns to visit and trust us when we say these small towns offer some of the best vacations you can imagine.

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