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Yahoo Travel: Five Charming Italian Towns You've Probably Never Heard Of

This originally appeared on Yahoo Travelon Monday, October 27, 2014.

Don’t get me wrong, I love the Ferrovie dello Stato (Italy’s railway system), but when I’m looking for a little 21st-century time travel, I drive around Italy’s messy regional roads because there are fairy-tale towns waiting to be discovered on top of and behind every hill. The Italian countryside is overrun with millennia of history, and the country’s 20 regions are all decisively different, which is why making a wrong turn always sends you in the right direction.

Here are five of my favorite places that I’ve discovered over the years.

Let’s start from the top…

Marostica

5 Charming Italian Towns You've Never Heard Of

The town of Marostica (Photo: Thinkstock)

When you wind your way into the valleys of the Veneto region, you are bound to come across crenelated castles and medieval villages perfect for a Shakespearean play setting. Just a half hour northeast of Vicenza is Marostica, one of those picturesque towns still rocking its 15th-century heyday, with a fortress gate, looming castle, surrounding wall, and piazza-sized chessboard.

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The biannual human chess match in Marostica (Photo: Frank Kovalchek/Flickr)

Yes, a chessboard. Marostica is all about chess. Every even-numbered year, the city hosts a living chess tournament in its main piazza, where players — pawns, bishops, kings, and queens — dress in early Renaissance costume to re-enact an epic poem based on Marostica’s 15th-century legend of two dueling families.

Related: Hitchhiking in Italy: The Worst Travel Decision I’ve Ever Made (Shocker, I Know!)

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A view of Marostica (Photo: Nicola/Flickr)

And every May, the town hosts a two-week-long cherry festival to celebrate the harvest — Marostica’s cherries are considered the best in Italy. If getting out of town is necessary, Marostica’s location is ideal for a whirl around the Veneto in search of Palladian villas in the areas surrounding Marostica, Vicenza, and Bassano del Grappa.

Where to stay: Albergo Due Mori

Gubbio

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The rooftops of Gubbio (Photo: Benito Roveran/Flickr)

If Veneto is about castles, Umbria is about color. Its vivid natural palette has inspired almost every color pigment made; local artist Piero della Francesca immortalized its countryside. Forget about Assisi, Spoleto, Todi, and Orvieto, and head northeast from Perugia to Gubbio, a jewel-box medieval town.

Related: ‘Mangia!’ We Ate and Drank Our Way Through Northern Italy

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A flower-bedecked walkway in Gubbio (Photo: Thinkstock)

High on the hill, Gubbio gives off an austere vibe with its monumental medieval architecture, such as the looming Palazzo dei Consoli and the Duomo. Don’t be daunted — Gubbio is a calm and almost meditative city, with wide-open piazzas, ancient Roman sites, and amazing century-old festivals. Gubbio has had a more than 500-year rivalry with Sansepolcro, hometown of della Francesca. Every year, top archers from both towns meet for the Palio della Balestra (alternately in each town), where archrivals vie for best bow. Everyone, and I mean everyone, from Sansepolcro and Gubbio is dressed in early Renaissance garb that some say is based on della Francesca figures.

On May 15, Gubbio strikes a pose as it celebrates patron saint Ubaldo in the Corsa dei Ceri, a race where three huge wooden candle-shaped columns are raced through the town in an all-day affair.

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The Corsa dei Ceri celebration (Photo: Martin Thomas/Flickr)

And if Gubbio is too sleepy for you, it’s easy to head out on the way of St. Francis, visiting Spoleto and Assisi, among other towns, or meander on the trail of Piero della Francesca paintings, which are found in churches and museums from Arezzo to Sansepolcro.

Where to stay: Hotel Bosone

Civita di Bagnoregio

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Hilltop Civita di Bagnoregio (Photo: Thinkstock)

If you find yourself lost on the way to Orvieto, look for Civita di Bagnoregio, which is in the northern edge of Lazio region. Thanks to its vertiginous isolation, Civita di Bagnoregio is a well-preserved medieval enclave of confusing alleys, surprise piazzas, and ivy-covered arches, and it’s practically all yours if you can make it up the steep, acrophobia-inspiring footbridge. The pedestrian-only town has as few as 12 inhabitants during the winter months.

Related: A Boozy Tour of Orvieto, in Italy’s Umbrian Countryside

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A doorway in Civita di Bagnoregio (Photo: ho visto nina volare/Flickr)

Visit on a foggy morning, and you’ll see a town that looks like a small island floating in the clouds. Once the sun shines, you’ll find yourself face-to-face with a tiny stone town that sits precariously on a massive rock.

Civita di Bagnoregio feels figuratively and literally on edge, so it comes as no surprise that the World Monuments Fund placed Civita di Bagnoregio on its 100 Most Endangered Sites in 2006. Bagnoregio can be either a quick pit stop — within an hour you can scale the bridge, visit the town, and head back down — or, as I prefer, an overnight affair. Where else than an impenetrable town is better for a tryst?

Where to stay: Corte della Maesta

Ortigia

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The waterfront in Ortigia (Photo: UminDaGuma/Flickr)

Lately, Sicily has gotten a lot of love — and with good reason. It has the best of Italy: food, culture, archaeological sites, beaches. And Ortigia is its trophy. The tiny island off of Siracusa in Sicily’s southeastern corner is a Baroque sandcastle mixed with Greek mythology. Take a 10-minute walk around and you’ll see ancient Greek temples, a historic fish market, a fortress, medieval neighborhoods, and a piazza with even more ancient temples, outdoor cafés, and a Caravaggio painting.

Related: Don’t Tell Anyone: The Last Secret Island in All of Italy

Ortigia’s location is key: It’s immediately adjacent to Siracusa, a city whose archaeological treasures include a gorgeous Greek amphitheater. And it’s perfectly situated for day trips to Noto and Modica, two beautiful Baroque towns also noted for their sweets. Modica, in particular, is the center for Italy’s chocolate production.

Where to stay: Sciuretta

Ceglie Messapica

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The streets of Ceglie Messapica (Photo: Thinkstock)

The Puglia region, in the heel of the boot, is a beautiful landscape of ancient farmhouses, coastlines, and castles. In Salento, the southern territory, sleepy Ceglie Messapica has reigned as “the center of Pugliese cuisine” for more than 90 years.

Related: The Most Adorable Italian Inns — That Won’t Break the Bank

The 15th-century town, a cramped diamond in the rough with its castle and crooked cobblestone roads, is bursting with flavor and culinary tradition. The restaurant Cibus is the place to test out seasonal, time-tested recipes, and it has perhaps the stinkiest and most well-sourced cheese collection anywhere. Surrounding Ceglie is a countryside peppered with trulli, those charming conical stone huts that look similar to the Seven Dwarfs’ homes. Many of them have been converted into bed-and-breakfasts that are trulli scrumptious (sorry, couldn’t resist).

Where to stay: Trullo dei Messapi

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The exterior of the hotel Trullo dei Messapi (Photo: Trullo dei Messapi)