It started with AirBnB - a photo of an actual legit cave dwelling flashed on my screen and I clicked on it, obviously.
Neither Cory nor I had ever heard of Pitigliano, to us it was just another ancient hilltop town somewhere in southern Toscana. There’s a few, they are all amazing. We noticed it was close to a lot of natural hot springs, so that seemed cool, idk.
When it came time to settle on where we were going, this one literally came down to a coin toss and we booked it as a result.
Fast forward to the middle of our trip, and we are in Alberobello looking at the coming days in Toscana and wondering if we’d have been better off with an extra couple days in San Quirico d’Orcia instead of packing up again and doing the two in Pitigliano. We both had it in our heads that San Quirico was to be our slow down time, but it turns out we didn’t have a lot of extra time there at all - somehow we messed up.
We’ve been moving a lot, and generally that’s not how I like to travel. You see so much but it’s exhausting, and I usually like to settle in a place long enough to have a favourite coffee shop, time to wander with no itinerary, imagine I actually live there, that sort of thing. Many times I have gladly foregone seeing more sights in favour of slowing tf down in this way.
Realizing our mistake we decided to take a look at the cancellation policy on the booking to see if we could switch up our plans, only to find we had missed the cancellation deadline by 12 HOURS. Every other AirBnB I’ve booked on this trip allows free cancellation right up to like 2 days before arrival, hilariously this was the one exception. It was out of our hands, and it felt like fate. We were going to Pitigliano.
Pitigliano is indeed an ancient hilltop town, and dates back to approximately 2,300 BC. It is carved out of and built up from the volcanic tufo rock that is prevalent in many places we have visited - much the same as Matera and even Napoli. It’s relatively easy to carve and dig into, hence why many of these places began as cave dwellings for ancient civilizations. It is also very strong, hence why these amazing structures have endured for millennia and still form the foundations of entire cities.
In the 1500’s it was owned entirely by one family, and its independent status made it a refuge for Jewish people fleeing systematic expulsion from Rome, Florence and other cities. The Jewish community grew and stayed for centuries and in 1841 made up over 11% of the entire population, higher than any other city in Italy before or since. It wasn’t always great - there is a ghetto area that survives to this day where Jews were confined for a time - but evidence remains of a vibrant community.
Walking the streets is an incredible experience. They are small, narrow, steep and winding. There are cats everywhere. You have to press yourself into doorways to avoid getting clobbered by passing 3-wheeled vehicles. So far, so Italian. But somehow this felt different. Maybe it was the fact we first walked it at night. Maybe it was the wine we drank in the sun that afternoon, or the insanely good meal eaten in a cave restaurant just prior. I mean, probably it was the wine. In any case, this town thoroughly captivated us both from the first moments.
Pitigliano is enchanting. This place welcomed us completely, gave us our best day yet, and left us both satiated and wanting so much more. We will be back - and we will take all the time we need.
This must be the place
After checking into our cave, we decided that aperitivo in the sun on our stoop was a must. We hit up the first little store we came across, just steps outside the old town, and it was AMAZING. The shopkeeper/owner was an awesome woman who helped us find what we needed, and when she saw us gawking at her back room (above) she beckoned us to another area that led to this ancient wine cave under the shop. WHAT!! SO cool!
Obviously this is also a great wine region, and this cellar was probably dug in some century BC for just this purpose.
Aperitivo on our stoop looking out over the walls of Pitigliano.
Next stop: dinner. We found an epic little restaurant in a cave, and the food was amazing.
Incredibly fresh carpaccio atop crunchy phyllo pastry with a full salad underneath :D! The rest of the meal was much simpler but even better, and involved truffles.
We wander the streets of Pitigliano by night…
This gorgeous tree stands over the main piazza. It’s stunningly beautiful and has such a presence.
Little shop window.
Heading home for the night…
Morning dawns cloudy but beautiful
We wander the streets by day, see some stuff
How many cats can you spot in this pic?
Here’s a closer shot to test your work
….and we will be back.
