small city passegiate night experience in West Central/Western Tuscany

Our favorite evening passeggiata in Italy was in Siena, along Via Banchi di Sopra, just as Rick Steves describes it in his Tuscany book. The street was full of people, mostly Italian, most dressed a lot better than we tourists were, walking and talking to each other, stopping to visit a neighbor, etc.

And with Siena, you get the added benefit of spending some evening time around Il Campo, which is right at the end of Via Banchi di Sopra and one of the greatest places on earth. We got seats on a bar's balcony, straight across Il Campo from the city hall and one floor up, sipped beers and watched people in the Campo for a couple of hours. It was one of the best things I've done in years. There are about six stools on the balcony (and a counter to put your food/drinks on) so we just got lucky to find the place empty when we arrived there after walking Via Banchi di Sopra.

Most towns have a passeggiata, but we liked Siena's best.

Staying outside of town on an agriturismo is great, and it makes a great base for day trips to other places, but it makes it hard to enjoy night life in a town. If you want to experience some of that night life (and again, it's hard to beat Siena), my own recommendation would be to stay in a place just at the edge of the old town walls, so you still have fairly easy driving and parking, but can easily walk to/from downtown in 15 minutes, or splurge and take a taxi, at least one way.

Siena is a 2-hour drive from the Pisa airport.

If you want a smaller town, Volterra or San Gimignano would be fine also, but probably not as good a passeggiata. Same advice applies, though. Don't get a place in the heart of the old town or you'll have trouble driving in/out and parking. Instead, stay and park just at the edge of town.

Of course, you could park outside and walk in for the night, but rolling luggage down cobble stones can be a chore, and you may have to leave your car unattended in a public parking lot overnight.

Thanks Patrick! I would never have guessed that about the bigger town, Siena, being more interesting than the smaller ones. That's great advice- had read what you had said about the driving and parking, etc-Will definitely use all of this info. Can't wait to see what you already have!

Personally, anywhere in Europe, I'd rather be in a lazy small town than a busy city, but specifically for a good passeggiata, "I luuuv Siena"*!

*Quoted from this article.

Definitely Siena. Even though it's a "larger" town, the older, inner core doesn't have a large town feel. Of the towns we have visited, it had the most pronounced passegiata and the main square is like a magnet at dusk.