Due to a late flight into Pisa having trouble on best way to start out the trip.
I have changed plans so many times for this trip it would make your head spin.
I would say things are mostly unchangeable at this point other than the first 2 nights.
Been to Italy twice before in the past 6 years but never with our daughter.
Would like to reach a city (not Pisa) and stay within the city walls. Ideally something medieval/ancient/historic with a feel that we would not get otherwise. I want it to be in the direction of our next location (Pienza)
We are taking our 3 year old daughter with us.
Not worried about crowds, want in some ways to get in the mood for the rest of the trip, so sleeping with windows open over a busy piazza sounds good to me and would definitely be my wife's preference.
The following day we want to not be too rushed and just spend the day and night site seeing and shopping in that town, walking only. My wife would like somewhere good for shopping (probably jewelry, possibly leather goods); even if just browsing and not buying
The first we are arriving very late so only planning sleep. Following day all day in same town and then check out next morning so really only 1 full day plus a couple of additional hours to stay.
Options are:
San Gimignano (actually have a reservation here already but can cancel)
requires us to rent a car in Pisa and would not reach hotel until around 10 PM.
I choose this over Volterra, Lucca, Pisa and felt it was a good size to not overwhelm us for the day and yet offer a unique experience of being there at night. it fits my criteria well but starting thinking there are better larger towns we might enjoy more or at least my wife would.
If we stayed here we would after checking out, drive to Siena with luggage and visit Siena for 4-5 hours before getting to Pienza late the following day.
Siena
This may be top of the list for me as although it skips the other 2 towns completely, we were planning on visiting here anyway for a good part of a day and this would give us more time in the city and I really do want to see the Duomo and the Campo
Piazza. It definitely has the medieval feel ; also puts us in Pienza much earlier on check out day so we would be less rushed on the 2nd leg of the trip for seeing the Tuscan Countryside by car from Pienza.
BUT this makes the night ride after flight longer and starting to worry about that. Parking here is worse as will be the walk from parking to the hotel so multiple concerns, would probably be an 11 PM check in which I need to find a place that is OK with.
Anyway this rough travel day got me thinking of a place I was planning on skipping:
Florence
An obvious destination for most, I left it off the trip plans because I was trying to include many other places that are otherwise hard to reach without a rental car, did not feel we had enough time to devote to it, thought many of the main attractions would not be good with a 3 year old, etc...
Thought we could see it when our daughter is older and on a trip that replies more on public transit.
I still fear each of those things which is why I am posting asking for advise.
On the plus side, it has the best shopping I assume for my wife and is much easier to reach from Pisa Airport.
The main sites look amazing and will surely fill up our site seeing day, but will it be too much/too rushed to see it in a day
With public transit we could check in at around 9 PM which is much more reasonable than we would be able to arrive in the other towns with a car.
The checkout day is more rushed though, as we might not want to leave Florence so quickly and have to get to a rental car place and drive out of town avoiding ZTL's and then onto Siena. By the time we reach Pienza it will be likely nighttime. Does it lack the medieval feel as well?
Reaching Pienza early is not an option as hotel is booked the first 2 nights and would like more of a city