What’s the first city that comes to mind when you think of Italy? You probably think of Rome and its Colosseum, Florence, Milan, or the canal city of Venice. 

While these are beautiful locations and can be worth a visit in your lifetime, these cities are unfortunately littered with tourist traps, big crowds, and subpar service that treats you like just another number. 

If you’re planning a trip to Italy, you may think you have to stick with the trendy “bucket list” locations, rather than going the extra mile to search for the up-and-coming underrated cities in Italy. After all, those trendy locations are mostly what you see on TV and what the big travel agencies and multi-national tour companies promote to travelers coming from abroad. Here’s the thing – when you’re stuck on bucket-list places that everyone and their dog knows about – you probably won’t experience Italy like a local and have the Italian adventure you’ve always dreamed about. 

Immersing yourself in the local culture and finally having your dream Italian vacation starts with uncovering the perfect place to base yourself – and that’s why we’re taking you off the beaten path.

Just three hours east of Rome is Italy’s Most Underrated City in the Southern Le Marche region: Ascoli Piceno! 

The Most Underrated City to Visit in Italy 
ascoli piceno le marche

Why Ascoli Piceno?

It’s located in Le Marche, a region of Central Italy revered as “all of Italy wrapped up into one region.” The city of Ascoli Piceno remains under the radar, offering all the charms of Italy’s well-known towns without the crowds. 

This up-and-coming status lends Ascoli to still being a city where you can meet the locals and truly experience the authenticity of genuine Italian hospitality.

Just a stone’s throw away from Umbria and Abruzzo, it is the perfect location to easily visit all three of these regions. The city is filled with architectural charm, boasting a history that dates back several centuries before the inception of Rome!

The Most Underrated City to Visit in Italy

Ascoli Piceno’s History and Culture

Once known as the City of One Hundred Towers, it is covered in travertine and is home to one of the Most Beautiful Squares in all of Italy, Piazza del Popolo. Travertine appears to “glow,” earning Ascoli Piceno its reputation as “The Italian town that glows at night” by CNN!

With a history that runs deep, having it’s foundations before Rome, there’s a local phrase that embodies the sense of being “Ascolani”: “Quando Ascoli, era Ascoli, Roma era Pascoli” (“When Ascoli was Ascoli, Rome was just meadows”). 

It’s hard to beat Ascoli Piceno for the genuinity of its people, local culture and its vicinity to the Adriatic sea, wine and truffle country. Unlike many of the towns of Tuscany that have been surrendered to tourism, the heart of Ascoli still beats to the rhythm of its 50,000 residents. This makes the city just big enough to support a local shopping and dining scene but small enough to maintain the authenticity and culinary heritage you want to experience. 

In the evening, the streets around the Piazza come alive, buzzing with energy, as friends meet to enjoy drinks. The city emerges for the nightly passeggiata (stroll) to one of the many restaurants in the historic center that are mostly blocked off to traffic. 

In Ascoli, you can take the evening in like an Italian, enjoying an aperitivo (cocktail) at Caffe Meletti (one of Italy’s 100 Historical Cafes, which was a favorite of Ernst Hemingway) or follow the tempting aromas to one of the Centro Storico’s (Historic Centre) many restaurant tables. 

Click here to read a local’s guide to pizza in Ascoli! 

Tired of the steep hill top towns of Tuscany? Then you’ll rejoice in the fact that Ascoli Piceno is easily walkable, allowing you to relax and go back in time while you cross its maze of tiny alleyways and cobblestone streets. The year-round mild and temperate climate allows for evening strolls or outdoor dining for most months of the year.

Want to know the best time to visit Italy? Read more here! 

most underrated city italy ascoli piceno le marche region

Things to Do in Ascoli Piceno and Surrounding area 

The hills surrounding the city remain uncrowded and hide many gems of the Le Marche region. There are many multi-generational wineries using indigenous grape varieties, both red and white, in full respect of the land. 

During cooler months, these rolling hills are coveted for black & white truffles, and you can even take a truffle hunting expedition when you join us on select tours!

Come the warmer months, from spring into early fall, a visit to the pristine beaches of San Benedetto del Tronto’s Riviera delle Palme (Palm tree Riviera), lined with numerous beach clubs and seafood restaurants, is an easy day trip from Ascoli Piceno.

Need to know what to pack for every season in Italy? Grab your FREE guide here!

Ascoli also maintains its rich cultural heritage with several local events throughout the year. 

La Quintana is the second-largest medieval reenactment in Italy. You’ll find hundreds of locals dressed in colorful traditional costumes representing knights in armor or dames in gowns at the medieval parade, an enthusiastic horse-racing competition, and a medieval joust! Events take place throughout July and August. A perfect evening activity to do during your free time when you join us on tour!

Mercatino dell’Antiquariato is an antique market held every third weekend of the month, hosting over 150 exhibits showcasing period furniture, sculptures, paintings, and local handmade products. 

And don’t forget the two festivals celebrating the Olive all’Ascolana, lightly-fried and stuffed olives made with the Oliva Tenera Ascolana – which you can learn to make when you join us on tour!

Got bucket-list FOMO? You can do both! Just 3 hours from Rome and a train ride away from Venice, you can tag on those bucket-list items before or after your trip with us. While you’re with The Italian On Tour, forget worrying about the language, logistics, or having a bad meal – you’ll travel stress-free knowing we’ve taken the guesswork out of planning your trip. 

most underrated city italy

How can I visit Ascoli Piceno? 

Whether you want to dip your toes in the turquoise Adriatic sea, delight in exclusive culinary experiences, wine taste at award-winning wineries, cook with local chefs, and truffle hunt at the height of Italy’s truffle season, The Italian On Tour has put together multiple small group itineraries that are perfect for experiencing Ascoli Piceno, nearby destinations of our neighboring region of Abruzzo and the hidden gems of the Veneto region.  

We’ll personally guide you and welcome you as family here in Italy! DIYing an authentic Italian experience isn’t easy without someone on the inside to show you the way – and that’s exactly where we step in. If you want to experience Italy’s Hidden Regions and best-kept secrets, Click here to discover your next Italian vacation today! We can’t wait to welcome you to Bella  Italia  and help you experience the real Italy!



most underrated city italy ascoli piceno le marche



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