La Piazza Blog & Stories
6 Italian Towns With Ancient Histories
June 24, 2019

6 Italian Towns With Ancient Histories


When we talk about ancient history, we’re talking very old, right? Ancient Rome was at first a small agricultural community founded circa the 8th century B.C. that grew over the course of the centuries into a colossal empire encompassing the whole Mediterranean Sea, in which Ancient Greek and Roman cultures merged into one civilization. This civilization was so influential that parts of it survive in today’s modern law, administration, philosophy and arts, forming the ground that Western civilization is based upon.

So, this is astounding to think about. Obviously, there are some villages scattered across Italy that reveal their “ancientness” in such an incredible, awe-inspiring way, we’ve included stays or visits to these ancient places on tours that pass through that region or area. Let’s just a review a few fabulous examples of some of our most favorite ancient–but not bygone–hang outs.

Two-Faced Ragusa, Sicily

Set amid the rocky peaks just northwest of Modica, Ragusa is a town of two faces: perched on top of the hill is Ragusa Superiore, a bustling center with sensible grid-pattern streets and all the trappings of a modern provincial capital, while etched into the hillside further down is Ragusa Ibla. This sloping area of tangled alleyways, grey stone houses and baroque palaces built on handsome squares is effectively Ragusa’s historic center. It’s quite magnificent.

Like every other town in the region Ragusa Ibla collapsed after the 1693 earthquake and a new town, Ragusa Superiore, was built on a high plateau above. But the old aristocracy was loath to leave the teetering palazzi and rebuilt Ragusa Ibla on exactly the same spot. The two towns were merged in 1927, becoming the provincial capital.

ragusa, italy

Ragusa’s pride and joy is the mid-18th century San Giorgio cathedral with a magnificent neoclassical dome and stained-glass windows gallantly sitting at the top of the sloping Piazza del Duomo. One of Rosario Gagliardi’s finest accomplishments, its extravagant convex facade rises like a three-tiered wedding cake, supported by gradually narrowing Corinthian columns and punctuated by jutting cornices.

And, of course, the local sea waters around Marina di Ragusa are usually crystal clear and calm. On our La Bella Sicilia ride, we always take a moment to stop, take in the views, relax–and maybe even a dip in the water!

Horsepower in Siena, Tuscany

sienna, tuscany

Ah! Siena. An absolute Medieval masterpiece. A city where the architecture soars, as do the souls of many who visit. Effectively a giant, open-air museum celebrating the Gothic, Siena has spiritual and secular monuments that have retained both their medieval forms and their extraordinary art collections.

horse sienna, italy

The city’s historic contrade (neighborhoods or districts) are marvelous too, being as close-knit and colorful today as they were in the 17th century, when their world-famous horse race, the Palio, was inaugurated. And within each contrada lie vibrant streets populated with artisanal boutiques, sweet-smelling pasticcerie (pastry shops) and plenty of great eateries. It’s a feast for the senses and of course one we feel is an essential stop on all of our Tuscan tours.  We love sharing this incredible place!

Uni Vibes in Urbino

Raphael’s Renaissance birthplace, the vibrant university town of Urbino, in the region of Le Marche is our second stop on the infamous Bike Across Italy tour.  

As history tells, the patriarch of the Montefeltro family, Duke Federico of Montefeltro, created a very hip art scene of the 15th century here, gathering the great artists, architects and scholars of his day to create a sort of think tank. More than a decade ago, the town’s undeniable splendor was made official by Unesco, which  claimed the city a World Heritage Site.

Graffiti Style in Orgosolo, Sardinia

High in the brooding mountains, Orgosolo is Sardinia’s most notorious “painted” town. Who knew?

Those of us who make it to this unique far-out spot can do no more than revel in the vibrant graffiti-style murals that adorn the village’s buildings.

Graffiti Style in Orgosolo, Sardinia

Its reputation is tied a bit to banditry that blighted this part of the island for so many years. But, in recent years, the city has gone through some reinventing of itself. A sort of ancient village facelift.

three italian residents sitting outside

Timid villagers peering through windows and narrow alleyways, come out to reclaim their streets at night; the old boys to sit playing cards and staring at anyone they don’t recognize and the lads with crewcuts cruise up and down on Vespas. Nearly forgotten in time, this special ancient town is a highlight on several of our Sardinia bike tours.

Truffle Gazing in Alba, Piedmont

A once-powerful city-state, its center sporting more than 100 towers, Alba is considered the capital of Le Langhe and has big-city confidence and energy while retaining all the grace and warmth of a small rural town.Alba truffles

Alba’s considerable epicurean reputation comes courtesy of its white truffles, dark chocolate and important wines. Its annual Fall truffle fair draws huge crowds alongside a stream of related local events and festivals. The vendemmia (grape harvest) remains refreshingly local and low key, but teeming with local enthusiasm.


The vine-striped Langhe Hills radiate out from the town like a giant undulating vegetable garden, replete with grapes, hazelnut groves and wineries. Exploring Alba’s fertile larder with two wheels is beyond a delicious pleasure. Words cannot do noble justice to this Northern jewel city.

An Ol’ Favorite: Gubbio, Le Marche 

Ciclismo Classico Founder Lauren Hefferon’s family ancestry hails from the sweet Le Marche hills, and as a result she (and we all) have had a long-standing (30-year to be precise) love affair with that rich, ancient gem town called Gubbio.

While most of Umbria feels soft, warm and rounded by the millennia, Gubbio is angular, sober, imposing and medieval to its core. Perched on the steep slopes of Monte Ingino, the Gothic buildings wend their way up the hill towards Umbria’s closest thing to a theme-park ride: its open-air funivia (cable car). The town’s stunning preservation is awe-inspiring and wandering its evocative streets, alleyways and staircases elicit textbook Italian dreaming.  This is something we all get to treasure on our Bike Across Italy trip.

Festival of the Ceri in Gubbio

The real story behind the Festival of the Ceri in Gubbio (a festival that annually coincides with our May departure) is that it’s one of the most ancient folkloristic festivals you will find in Italy and it reveals both religious and pagan origins; a pagan festival in honor of Ceres, Goddess of the Harvest, Glory of Communities, Renaissance Power. Others speculate that in 1154, these were celebrations after the victory of Gubbio against 11 allied cities. The most likely story is that of the Eugubini themselves, named after Ubaldo Badassini, Bishop of Gubbio in the12th century, felt inspired to celebrate. Beloved by his people, Ubaldo died on May 16, 1160 and the locals responded with a pilgrimage including illuminated candles. Since that year, the procession del transito (movement) has been organized on the eve of Ubaldo’s death, with the offering of votive candles. Which of these legends is true? We may never know. But, it’s a great party.


Join us to experience these ancient towns on any of the above mentioned bike tours and see history unfold before your eyes.

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