Country Roads: Scraping the Skies of Medieval Italy

Long before Peter Minuit, the Director of New Netherland, a Dutch colony founded in the New World, purchased the island of Manhattan from Native Americans in 1626, there was already a place back in the Old World that had established itself as Skyscraper City: San Gimignano.

Repeat after me: sahn jeem-een-YAH-noh. Perfetto!

Originally an Etruscan village, San Gimignano, or San Gim, evolved into a medieval walled city perched on a hilltop overlooking kilometers of undulating vineyards and olive groves in the province of Siena in Italy’s Tuscany region. Known throughout the Bel Paese as the Town of Fine Towers, in 1990 the United Nations Educational, Scientific and Cultural Organization (UNESCO) proclaimed San Gim’s Centro Storico (Historic Center) a World Heritage site.

The intrepid “band of merry media” and I, guests of Insight Vacations‘ (Insight) abbreviated Country Roads of Italy journey through Umbria and Tuscany, just hopped off the motor coach in a large parking lot only a few paces outside the main arched entryway into the past.

Lens caps off, we’re already shooting away at the rock and mortar while we follow close behind Belinda, Insight’s tour director/concierge/storyteller, as she begins to paint the scene.

Country Roads: Scraping the Skies of Medieval Italy | ©Tom Palladio ImagesBack in the early 12th century, she begins, the peace around San Gim came apart as the two political factions of the time — the Guelphs, who supported the Pope, and Ghibellines, who favored the rule of the Holy Roman Emperor — faced off in a bloody civil war that would last nearly 200 years.

But, why so many towers?, someone interrupts.

This struggle for dominance also involved a battle for prestige and status, Belinda continues, as both political factions, along with their allies, built tower houses to outdo the other. The higher one group built, the other group would quickly top it.

She adds, By the end of this “construction boon,” San Gim’s skyline was dotted by no less than 72 towers, some reaching as high as 70 meters, or 230 feet.

Country Roads: Scraping the Skies of Medieval Italy | ©Tom Palladio Images

Before we can scatter in a hundred different directions with our camera gear, Belinda tells us that, Only 15 of the original 72 towers still remain today, as some were demolished in battle while others were reduced in height once the civil war was over.

She concludes her open-air, History 101 lecture by informing us that, Towers aside, the city was later brought to its knees by the dreaded Black Plague and eventually lost its independence, falling under the rule of mighty and powerful Florence.

This well-kept medieval town is, without a doubt, my fave locale thus far on this Insight Country Roads journey. Maybe it’s all these towers climbing upward to scrape the sky, coupled with the great street scenes below and peekaboo panoramic views outside the walls. Whatever the reason, my cameras and me are having a field day capturing photogenic San Gimignano.

Just click on the frames below for full-screen views of what we’ve framed thus far.

Midway through our visit, the “band of merry media” agrees to muster around Belinda in Piazza della Cisterna, San Gim’s prettiest square lined with shops and outdoor cafes, for an Insight SIGNATURE moment.

Care to meet the World Champion of gelato makers?, she asks. His shop’s right over there and I’ve got vouchers for each of you for a complimentary tasting of his artisan ice. What do you say to that?

All together now: GELATO! GELATO! GELATO!

Take Me along, Country Roads | ©Tom Palladio ImagesFor complete information on Insight Vacations’ 12 Italian premium and luxury-escorted itineraries and over 100 journeys throughout Europe, just click HERE, or call toll free (888) 680-1241, or contact your travel agent.

I’ll save the, I scream, you scream, we all scream for ice cream scene for my next dispatch when we get up close and personal with San Gim’s fun-loving, World Champion gelato maker: Sergio Dondoli.

Ciao for now.

©The Palladian Traveler

Borsalino w/ props SMALL | ©Tom Palladio Images



  1. Lovely blog Tom and the photos are great too. San Gimignagno is such an interesting town with – if I remember correctly – a particularly gory painting of San Sebastiano, riddled with more arrows than usual, in the Duomo. Did you see it? San Gimignano was also featured in the excellent movie “Tea with Mussolini”, where it was shot. Orna

    1. Vicina — Along with “TwM,” San Gim was also used by Zeffirelli to double as Assisi in “Brother Sun, Sister Moon.” And, no, I didn’t go inside the Duomo, I was on the clock with my band of merry media and only saw the sights from the outside. Next time, for sure, I’ll dig a little deeper. Glad you liked it. Look for the follow-up post later today/tomorrow on San G when I feature the World Champion gelato maker. Ciao ciao.

  2. A wonderful place – so evocative of the Middle Ages. I’ve been there twice and approaching it is magical. I think E.M.Forster set ‘Where Angels Fear to Tread’ there.

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