Tuscany - 12/26 - 1/7 (Xmas Markets, How to Travel Tuscany)

If you visited every place on your list you could easily spend a month to do it, so it's a good thing you "usually get up very early and have very long days and love to see as much as possible"! Daylight is short this time of year so be aware which sights are enjoyable after dark and which ones not.

You've named plenty of lovely, charming towns; none of them are duds IMO. To decide which ones can realistically fit into your available number of days, you might consider RS principles of staying in each place 2-3 nights (no 1-nighters) and allowing 1 day per week to relax, do laundry, etc. (in your case with 12 nights total, perhaps 1 full day and another 1/2 day). Following those principles, decide on no more than 5 "home base" locations and which other destinations, if any, make convenient day trips from each base.

Driving in snow? Well, the most important rule is to go slow. The slightest curve can suddenly make you feel like the car is on a skating rink instead of a road. Figure that even on highways, your top speed may be 40 mph instead of 50-60 or whatever the legal speed limit is. If a real blizzard comes in, you may have to stay an extra night wherever you are when it comes. Of course, it might not snow, but you're wise to plan for it and even w/o snow you could encounter rainstorms. In any case, your last night before departure should be in Milan near the airport. You don't want to be stuck somewhere because of a snowstorm, road closure, transit strike, or trying to turn in your rental car and suddenly all the rental company's computers are down.

For Tuscany I would suggest basing in Florence and then taking a tour into the country side. Rick always recommends Tours By Roberto (which we are doing next week). They come to your hotel, Pick you up, take you site seeing, wine tasting and to an agriturismo for a homemade lunch. The price is really reasonable and they hit your key towns. The nice thing is that you get to see as much as possible during the day and then your back in Florence for any night life, because the country side will be quiet this time of year.

Yeah, last time we hit Italy for 3 wks we spent 2-3 nts in all locations (Lake Como, Venice, Florence (actually Greve and rode school bus in each day, Cinque Terre, Sorrento and Rome. Was amazing.

Was kinda thinking:

1. 12/26-28 - Verona (hitting Verona 1st nt, 2nd day and possibly Padua later in day??)
2. 12/28-29 - hitting Padua (unless saw it yesterday afternoon/early evening), then Bologna, then to Florence
3. 12/29-1/1 - Florence
4. 1/1-2 - Volterra & San Grig staying in 1 of them
5. 1/2-1/6 - either Montalcino/Montepulciano/Pienza - but seeing all of these in that timeframe
6. 1/6-7 - Milan nt b4 & fly out 1/7

Only thing is, wondering how it would be to stay in Greve and rearrange. We stayed there years ago at Il Cassello but went horseback riding down the hill with Eva as Poggio Asciutto and ate dinner with her family and would love to stay there and see them again but emailed & no response & not seeing good contact info online for them. What do you all think about above or other options? I have never had a hard time planning a trip before. I do like the idea of Roberto, the tour guide, I need to look him up & prices.....

I would think the temperatures would be moderate in Tuscany--47 degrees at night and 53 degrees in day on average for December. Snow would be more likely farther north--up in the big mountains of Northern Italy.

Tuscany is a place that's best seen from behind the wheel of a rental car. The roads are well paved and well marked--but just a little crooked. I never had any road maps or GPS, and still didn't have any problems getting from Florence to Siena to San Gimignano to Volterra to Orvieto by car.

The good news is that you can take a fast train out of Milan to any major Italian city, and you can do day trips out of the bigger cities if you choose.