Okay, I’m back. Just a bunch of random thoughts.
We stayed in Siena for a week as base camp for Tuscany. There’s lots to explore in the city so make sure you bring good walking shoes.
Surprisingly, the wine in restaurants is very reasonably priced. More than fair from an American perspective so we always purchased a bottle at the owner/waiters recommendation.
Osteria La Mossa - Right in the corner in Piazza Del Campo. Excellent food and small joint. Right next to it is a great place for drinks outside looking at the Campo but probably not something for winter. I got the Tuscan traditional dish, pici con cinghiale, pasta with wild boar ragu. OMG
San Paolo Pub - best place to watch the happenings in the Campo. It’s a tiny bar on the second floor with small balcony that seats about 8 uncomfortably. Amazing view. Perfect for grabbing a drink.
La Vecchia Latteria - Best gelateria in Siena. I tried them all.
https://goo.gl/maps/8uLQak7yGSS2
La Proscuutteria - Funky hipster place in a 500 year old building with stairs that go down, down, down… Check it out for a beer, wine, and meat and cheese plate.
They do a decent pizza in Siena and there’s a pizza joint on every corner. We typically would hit up a place off the beaten path when we’d run across a building with a door, oven, and only enough room to stand. They were the real deal.
You’ll need a car if you’re going to cover distance (Montalcino and Montpulchiano) and there’s a Hertz near the train station. We would just walk down and grab the car and take off.
https://goo.gl/maps/C6aeGEBxypL2
There is NO parking in Siena. I’m not kidding… Can’t even drive a car into the city unless you have a pass. There is ONE free parking lot and it’s call the Free Parking Lot or the Penny Market Parking Lot because there’s a Penny Market across the street. If you park there then you’re either walking back up to the city or there’s a bus stop right there that will get you to the top.
https://goo.gl/maps/RVD6SoWd6VG2
You’re gonna want to get to Montepulciano, depending out how much you guys ride you could actually bike it. Take the back roads, probably want too stay off the main “SR” roads and they’re not very pretty. You could also ride to San Giamgiano, amazing! Riding out to the southeast towards Asciano, Tuscan postcard type roads and scenery.