I am working out the final 3 nights for our trip this coming June. We will coming from Volterra (by bus) and I am considering staying in either San Gimignano or Siena. I know both will be crowded in the day, but is one less so than the other? If you had to pick, which one and why? Also, we have an 11am flight out of FLR on a Monday, so we are trying to decide if it be best to spend the last night in Florence close to the airport. We don't want to have to leave at the crack of dawn to get to the airport from, but since we are using public transportation, we are not sure of the the best option. Does anyone have experience with the "Airport shuttles" offered at some of the B&B's in Siena? It seems like it would take a lot of the hassle out of getting to FLR, but most do not list the price of this service. It would also allow us to spend the full day on Sunday in Siena. I haven't seen any shuttles offered in San G yet, but I am still looking.
No doubt for me, Siena.
It looks much more crowded in San Gimignano as it's a much smaller town.
More things to do, to visit also while you are there.
Of all hill towns in Tuscany, i thought San Gimignano was the most touristy, in a negative way, a'ost Disney'ed if you understand what I mean. People say that it is a nicer village when we visit either early morning or at night when autocars aren't there.
I don't have experience with shuttle buses.
I would personnally sleep in Florence the night before departure, just in case something happens to a scheduled bus.
Siena and Florence before your flight. Too many potential problems traveling on flight day.
Not been to San G, but had a very enjoyable 2 nites in Siena.
I also suggest spending the night before your flight in Florence.
We are currently staying in Siena for 3 weeks, and it does not feel crowded (except a little on Saturday evening when everyone is out strolling). I'm not sure if it will be a lot different in June. There is plenty to keep you interested for 2-3 days. It is beautiful at night.