December trip: Venice > Tuscany > Rome Itinerary (edited draft)

Two night in Venice will give you only the arrival day (which will probably be a jet lagged fog) and one other day. That really doesn't do justice to one of the world's most unique cities. Strongly suggest a minimum of three full days for Venice. You can easily take one day each from Tuscany and Rome, and still have enough time for both of those locations.

We’re doing a somewhat similar itinerary and devoting two full days to Venice plus parts of another. Shaving time from Tuscany or Rome makes sense for at least one more day there.

Hi, just wanted to comment on the 18th, it looks like a really busy day.

In October 2023 we were staying in Siena and took a day trip also visiting San Gimignano, Volterra, and Monteriggioni: https://www.viator.com/tours/Siena/Small-Group-San-Gimignano-and-Volterra-Day-Trip-from-Siena/d944-5493SANGIMIGNANO with https://www.tuscanescapes.com/ . We had maybe 45 minutes to an hour in each of the three places, and felt that wasn't enough to really enjoy it (find a WC, buy a gelato, and it's time to find the meeting place). I hope you can be more efficient in the driving and have enough time to enjoy! For example, in Volterra we wanted to see the Etruscan museum, but we didn't even find it before it was time to head to the meeting point.

A suggestion for "explore Siena": we hired Anna Piperato https://www.sienaitalytours.com/ and we recommend her deeply.

Thanks everyone for your feedback! I’ll probably shave off a bit from the 18th as recommended

Wednesday 18

Arezzo is wrong direction and no time for this town today
Remember it will be dark by 4:30-5 pm

Thurs 19
Be sure you have a designated driver for all days you plan to drive and visit wineries
The alcohol limits are way lower than US
One tasting can put you over the top

Friday 20
I assume you will take bus or train into Florence
( parking will be well outside center and driving into Florence NEVER recommended)
Please read up on ZTLs if you haven’t already

Saturday 21
This is the day you will pick up husband at FLR?
Do a search here for best place to park for the day. You will have his luggage in the car, be sure to carry his valuables with you today
Or
Post a new question asking for info on parking- I am sure Roberto, our resident Florentinan will respond. Listen closely to what he says.

Sunday 22
Probably OK
Might not have time for hot springs

Mon 23
I assume you will drop car in Siena

I suspect you have too much planned right now for each day but you will be fine tuning and figure that out. Be brutally honest about how long things take. If Google maps says 30 min, it will most likely take closer to 45 or more.
Get up and going early so you are not driving the Tuscan roads in the dark.

Oh- also add a night to Venice
You won’t regret it

Sounds like a fabulous trip
Tuscany AND Christmas markets!

14-16:: I'd stay 3 nights in Venice.
18: Too many places in one day. Distances may look short on a map, but it takes a couple of hours from Siena to Arezzo, once you factor in the time necessary to find and drive to the parking lot and walk to the city center. Also you'll need at least half day to see Arezzo. Then you need at least 2.5 hours for the reverse trip from AR to Volterra, even if you totally skip Monteriggioni. Where are you going to find that type of time in December when it's dark by 5pm?
21. Very busy day. Don't forget you have only a few hours of light in December. Even without stopping at all, the drive from Siena to Florence on the SR222 is two solid hours of driving on very curvy narrow highway. Are you prepared to do that in the dark?
23-30. I'm assuming you meant you are going to drive to Rome, where you will drop off the car upon arrival. If you have a car makes no sense to take the train from Siena.

Moral of the story, you need to curb your enthusiasm and cut down your expectations. You can only do so many things on any given winter day. Daylight is short in December.

PS: Carrying chains or snow tires is mandatory in Tuscany between Nov 15 and April 15. Make sure your rental provides you with chains.

There is a small admission to the Duomo Museum ( well worth it !! ) which also includes the bapistry

It looks like you've put a lot of thought into this trip. However, I think your pace is unrealistic and frantic.

For instance, you plan to devote an afternoon to "Drive SS 222, Chiantigiana connecting Siena to Florence: explore villages castellina, radda, greve, panzano". There will be no exploring those villages, you'll barely have time to just drive through them.

We spent a week in Chiani using an agriturismo outside Greve as our home base. I'm very familiar with the Chiantigiana and visited every village you mentioned. I'd budget at least a day for seeing them, the better way would be to budget a half day at each. By trying to see too much you can end up seeing nothing.

I'd also set aside at least one day with a completely free schedule. There's been lots of times on trips where we discover something completely unexpected. By building in some wiggle room, we were able to take advantage of the opportunity and it has led to some of our fondest memories.

I hope you have a wonderful trip. Italy in December is great, there's lots smaller crowds, the weather (at least on our trip) is good and you can get more attention than during the high season.