6 Fairy-Tale Small Towns In Italy

Italy’s historic cities and towering artistic heritage get the lion’s share of attention from travelers, but a word to the wise: the magic of this storied land is often found far from the big city. There are more small Italian towns that look like they belong on the pages of a storybook than you could count. So if you’ve had enough of towering cathedrals and world-renowned museums, consider adding one of these six too-picturesque-to-be-true Italian towns to your itinerary.

Orvieto

This one’s a little closer to the beaten path, but for good reason. A dramatic hilltop setting atop a towering bluff, a 700-year-old cathedral, a fascinating underground world: it’s easy to see why Orvieto is many a traveler’s favorite day trip from Rome. And while the Duomo (cathedral) is a very obvious highlight, as are the narrow streets and the view from the top of a thousand-foot volcanic bluff, there’s one Orvieto sight you shouldn’t overlook beneath the surface.

Not all of Orvieto’s attractions are above-ground. Ever wanted to eat in a cave? No problem - eat underground at Le Grotte del Funaro and you’ll feel like you’re descending into the lair of some storybook creature. Or simply climb down the ingeniously designed Well of St. Patrick, a Renaissance engineering marvel you can go inside. Will you want to dedicate most of your day to the above-ground beauty of this dense town seemingly teetering at the edge of a cliff? Of course. But half the fun is underneath.

Monforte d’Alba

Italy’s mountainous far north is often short on visitors and rich in scenery, and every so often you’ll stumble upon a town there that you almost won’t believe is real. Case in point: tiny, colorful Monforte d’Alba, set against a backdrop of the rolling foothills of the Dolomites.

You don’t need to plan much to enjoy this stunning town. Turning up ready to explore its winding cobblestoned streets, search for the best vantage points from which to ogle the sprawling fields and mountains in the distance, and drink the renowned local Barbaresco wine is about all you need. But one recommendation we will make: dine at the Osteria dei Catari, if you have time. It’s a much-recommended spot for local meat and pasta specialties.

San Gimignano

It’s no surprise that San Gimignano falls on the Tuscany tourist trail. A UNESCO World Heritage Site that lays claim to the so-called “world’s best gelato,” it’s got all the trappings to draw the crowds - and draw them it does. But visiting at off hours will show you exactly why everyone wants a piece of this fairytale town: surrounded by stone spires on a promontory overlooking the countryside, nowhere else will you feel so much like the ruler of a storybook kingdom.

Since San Gimignano is one of the few Tuscan hill towns with intact medieval towers, spotting the seven spires is one favorite pastime of visitors. Take in the view and a good meal from the Piazza della Cisterna. Oh, and that world-famous gelato? That would be at Gelateria Dondoli. As to whether it’s worthy of the “world’s best” designation, well, you’ll have to judge its merits for yourself.

Spello

If squeeze-through cobblestoned streets winding up and down hills are your idea of the perfect day out in Italy, make your way to Spello in the central Italian region of Umbria. You’ll see baskets of flowers everywhere, and, when the Spello Infiorata festival takes place every June, huge tapestries made entirely of flowers all over town. A Roman aqueduct has been turned into a leafy walking path. And if you’re looking to leave Italy with a bottle of olive oil, this tiny town boasts some of the best in the country. Spello is the kind of place where nearly everything warrants a picture - clear space in your phone’s storage before you go, or you may just find you run out.

Taormina

Visitors to Italy have to make a real effort to get to Sicily, an island in the country’s far south, but those who do will be richly rewarded. That’s especially true in Taormina, where you’ll find a Roman amphitheater with outstanding views of a turquoise harbor and elegant checkerboard-paved piazzas amidst the rocky hills of Sicily.

There’s plenty to fill your time in this popular spot. Eat in a cafe along the Corso Umberto, the only street running all the way through town, for the most concentrated dose of its charm. The Teatro Antico, a Roman amphitheater high above the town, is a must. And be sure to admire the view from Piazza IX Aprile, boasting sweeping views and street performances alike.

Varenna

Nothing about Lake Como, one of the world’s most photographed lakes, could ever be called “off-the-beaten-path.” But if it’s fairytale towns in Italy that you want, you’ll have to concede: this magical place where Renaissance villas ring sparkling blue waters is popular for a reason. Varenna in the Province of Lecco, one of the least-visited of its surrounding towns, is the happiest available medium between seclusion and the Instagram-worthy beauty of the lake’s best-known towns.

In keeping with its lower crowds, Varenna is a relaxed place. A stroll along the waterside Passeggiata degli Innamorati walking path and a visit to the Villa Monastero, a former convent-turned-villa which offers views both indoor and outdoor, and a notable botanical garden, begin its list of higlights. Then, we know you’ve been waiting to hike up to the Vezio Castle to view Lake Como from above. And, of course, leave plenty of time simply to wander, admiring the storybook setting.

Though there are probably thousands of Italian towns that look like they leapt from the pages of a fairytale, these six are as outstanding as they are diverse in scenery and appeal. So if you’re looking to get out of the city, start here: these towns have little but glowing reviews for their storybook charm.