Don;t know where you are planning on spending Dec 24th and 25th - but you need to realize that most everything will be closed. Be sure you know that anything you plan on seeing or doing - or eating at - will be open - before you leave.

I am not a fan of countryside in winter - but I am a city person - generally the bigger the better. I like visiting small towns - but it I have to spend more than a night or two in one I tend to get really bored.

Renting a car and visiting a different town every day would be interesting - unless you get bad weather - in which case the local roads you will be using may not be in drivable condition.

I would get more detailed info on the holidays and opening time of sights before finalizing your plans.

I guess it depends on how much you enjoy the "luxury resort" aspect of things. I would never book a trip to Tuscany in the middle of winter (well, I would if I had infinite resources or someone else paid for it). Nor would I ever be inspired by the NYT. The countryside is brown and scrubby, it's cold and bleak. It's true it will be relatively tourist-free...guess why? Hell, I don't even like my own house in France in December, and you couldn't find a place closer to my heart than that.

Rome as a daytrip? Hell, no.

My advice, FWIW, is to head to a city. That's what, I think, sensible people do when vacationing in Europe in the dead of winter. Or,just go to the luxury resort and have a luxury resort experience, which might or might not be even remotely European.

Thanks NY Traveler. We would be near Siena on Christmas Eve and Christmas. We have scheduled a trip to San G. And Volterra on 12/24 and have confirmed everything we are interested in will be open. Christmas will be a Siena half day guided tour with well reviewed guide then meal at hotel. We may play with the days a bit as I'm worried about driving in bad weather.

We do enjoy the "luxury resort" aspect of things and don't view that as being a bar to having an authentic trip. I noted that merely to establish that we are not staying in an isolated place with no amenities in the event of inclimate weather. We do plan on being out of the hotels for the days provided that the weather cooperates.

St cirq., you seem like you're very knowledgeable but your delivery can be very aggressive which undermines your message. "sensible people" and so forth, and I've noticed on other threads I've read and directed towards others. One doesn't have to rent a room in another person's private lodging in a weird apartment in Paris to have a great experience.

I've been to Italy for Christmas, but only Rome, which is very festive that time of year. Have also been to Venice in the dead of winter and had a delightful time.

I am a Rome lover--the vibrant buzz and slight edge of the Eternal City get my heart a-racing, but I know that many do not share this sentiment. However, I wouldn't go to Rome as a day trip. That's the worst way to experience Rome, IMO.

And although I too prefer the countryside in warmer seasons, it sounds as if you have planned your trip well based on your own interests. I'd stick to it and approach the experience with a sense of adventure. If you're rained out and have copious wine and good food, who cares?

Enjoy your holiday.

FYI, if you do more research, you might be able to find a better place to have dinner in Siena for Christmas. Siena isn't really that small of a town; it's both a college town and highly touristic, so I should think Christmas there won't be a problem if you plan well. There's much to see in Siena, so you could easily skip San. G and Volterra (or just skip one of them) if you desired.

I spent NYE and New Year's Day in Assisi once, and we didn't get a chance to do all we wanted--and I'd been to Assisi before, too.

The problem staying somewhere so remote (your resort is remote) in winter is it will be dark around 5. Unless you plan to eat all of your dinners at the resort, then you won't enjoy driving those curvy roads in the dark. I would cut back the number of nights at the resort. In summer, when it stays light until 9:30 or 10:00, then it's more practical staying somewhere remote.

Since Rome is only 90 minutes by train from Florence, you could easily train there for a day trip.

You're thinking of spending 5 nights (4 full days) exploring Siena, San G, Volterra, 2 Chianti wineries and 1 Brunello winery. That's a lot to cover in the time available, especially in late December when you could encounter rather bad weather and will have only about 8.5 hours of daylight every day.

Driving to Siena, San G and Volterra requires some research before you go because you need to identify where you're going to park and how you're going to reach the parking without violating the limited traffic zones (and getting traffic tickets in the mail months after you get home).

The Four Seasons in Florence is probably fairly easy to reach without violating the limited traffic zone. Just make sure the hotel provides explicit instructions. That's the good news. The bad news is that the Four Seasons, while one of the nicest hotels in Florence, is not near the main tourist sights. It's nearly a mile from the Duomo, so you'd probably be using a few taxis. Because most of the historical center is pedestrian only, you should make note of where the taxi stands are located.

Where is the Brunello winery? Montalcino is at least 90 minutes each way from Castello di Casole, and longer if the weather is nasty.

is this your tuscan resort?

http://www.castellodicasole.com/hotel

[it's a good idea to post the link to places you mention so that those who are trying to help you don't have to find it for themselves]

there would certainly be worse places to be stuck in bad weather, though i was a little surprised at how long it took me to find out anything about the food. [they have a restaurant and a pizzeria, so far as i can work out]. but i have to agree with the others that it wouldn't be my choice for a place to stay in the midst of winter.

personally i would think about reducing my days there -[ !'d got for 3 nights] finding somewhere in Siena itself for Christmas, and then ending my stay in Florence - though it's a shame you'll be leaving on the Sunday as the Four Seasons does a terrific buffet brunch on a sunday which it would be a shame to miss.

have a great trip!

mah1980 - Congratulations on your first trip to Europe. No matter where you go it will be a unique experience. Don't know if you've booked through a Four Seasons Preferred Partner agency, but if you do... you may get better prices, a room upgrade, and you would get FREE amenities at the Four Seasons Firenze... BTW, it's an INCREDIBLE hotel!

That all said, I'd encourage you to reconsider your options. Not to be critical, but heading to Tuscany in the winter would be perhaps like going to Sonoma in the winter - might not be much going on.

For your first time in Europe - especially Italy, why be isolated in a small town/area with limited options and exposure to "Italy?" Staying at resort is great but with the darkness, weather, drive distance, etc. ... you will probably STAY THERE - especially at night, as mentioned above.

Because you're isolated, your "location" could be anywhere in the world. Heck, it may seem like you're staying in the Napa Valley! If you're going to "come to Europe" I'd suggest NOT to isolate yourself... but rather put yourself in a place where you can embrace the culture and experiences you want to have.

And you can get a resort lifestyle just outside Rome. Or you could stay at a property like the Hotel de Russie and be wowed IN Rome. I say this because Rome at Christmas is a blast - I lived there three years and every night there are events & happenings during the season.

I realize this may not be your "cup of tea," and even if it's not, I'd say reconsider being out in the "country" this time of year with the weather, closures, darkness, etc. At minimum, if you want to stay in this area, get closer to Siena, Lucca, Bologna, or a larger city so you have more options. I'd hate to see you go to Europe for the first time and spend most of your time on a resort - staring at four walls - secluded from the world due to circumstance and timing. (Granted, it's be a NICE four walls).

I often help people with trips and frankly it's hard to give any advice without "talking and discovering" your interests... But in your messages I "hear" your doubts and second-guessing. There's still time to change, so I'd sit down and ask yourself, "What kind of experience do we really want?" And the key word there is "WE."

For me at Christmas, I'm a city guy also - Give me Rome, Paris, London, the XMAS markets in Germany, Strasbourg, Vienna, etc. But only you know what YOU want. For what it's worth - Here's a post of some events and happenings in Rome one Christmas Season - Good Luck!

** http://tinyurl.com/ycda3w3 **

Greetings. Your resort looks Fantastic! I don’t often have the opportunity to stay at luxury hotels, but when I do - ah, the linens, the views, the service, the food. Nothing like the royal treatment. That said, it is a good idea to heed the advice about the season. Short, cold days. If it rains (or snows) even driving can be a problem - never mind walking around in it.

Winter will mean no martinis on the terrace, no strolls through gardens, no grape picking. Sometimes winter months at resorts look like a bar after closing and they’ve turned the lights on. No atmosphere at all. So indoor activity is what you’ll have. Wine sampling sounds like a GREAT indoor activity. If you are certain your expectations aren’t too high with regard to what you can accomplish, taking potential weather into account, you can have a lovely time. Your resort doesn’t seem to have any events planned for Christmas Eve or Day. Not even a little caroling. But verify that. So, depending on how you feel about that holiday (cozy fire, snuggly chair, good book, wine, your sweetie giving you a beautifully wrapped diamond bracelet -- okay, never mind, that’s my dream), you might want to stay in a town where there will be some celebrations.

I was in Rome once in January and it was quite tolerable, but once heading north, it was cold. My friend bought another coat - full length - in Florence just to keep warm. And Florence. Well, I know some people love it. Once done with the art, I was ready to open a vein. Have been back twice - and will overnight if I must - but otherwise I don’t understand the lure. And it seems a mean-spirited little burg, handing out tickets to unsuspecting tourists who have already dropped a bundle. Siena is wonderful, although many of the streets require brakes on your shoes, they are so steep. Could be treacherous if there is freezing rain. Parking isn’t really a problem; lots of garages with easy to spot signs. But then there is the walk.

I’d choose Rome for the holiday (it’s not a day trip), then go to the resort to relax and allow yourself time to relive what you’ve experienced in Rome, and make those trips for wine tasting! Whatever you decide, have a fantastic time!

Personally, I would be spending my vacation in Rome doing day trips out of there if you need to see more.Besides working for a major US airline, I studied a semester in Florence in college.
That said, I have been back to Florence and Sienna several times and it still doesn't get me excited like Roma!
I would think that you would find more things opened and to do at that time of the year in Rome which is one of the most popular cities in the world!Rome is NOT a day trip,trust me!
Where you are going is beautiful in spring and summer when things are blooming- but pretty quiet/dismal in the wintertime.
Siena is best enjoyed when you can sit out on the square with a coffee to people watch.If you stay with Florence,go up to Fiesole(12 minute bus ride from the David) to have unbelievable views of Florence and visit the Roman ruins there!

I know that I will get "flamed" for this but going to a resort to me is negating the whole Italian experience which is unique.You are not getting out to the food and flea markets;navigating little restaurants with Grandma's cooking,meeting the "natives" in their own environment,etc.

My questions to you would be:
Are you sure that these wineries will be open at that time of the year i.e. right before Christmas? I have found in my travels around Europe that alot of these places are closed during the weekdays after the "tourist season" and during holiday months.

The weather can be rainy and sometimes chilly where you will be-do you have a PLAN B if the weather is terrible? There are only so many art museums one can do?

I have driven all over the world but Italy is tough for a first timer in the cities-would definitely recommend getting an automatic!Parking is always a pain in any European city.

Everyone on these Fodors' boards wants others to have great trips and become travel junkies like we all have become. When people come to these boards to ask questions or concerns, one has to be accepting of the seasoned veterans of travel and their opinions-we are truly just trying to make your trip fabulous!

My mantra is: Rome is like a artichoke-the more you peel away, the more you will find that it has something for everyone!
Have fun!

Italy has very strict drunk driving laws. So the designated driver should not indulge in the wine much if at all. That means if you both want wine with dinner, you'll need to eat at the hotel/resort.

Please don't let people talk you out of Florence, if that is where you think you would like to stay. I have been to Florence (and Rome, for that matter), in both summer and winter, though not at Christmas, and I had a great time in both seasons. Rome is a wonderful city, but I love, love, love Florence. You may or may not feel that way, once you spend time there, but please don't write Florence off. I have enjoyed hiking in rural Tuscany in winter, but I haven't stayed there during cold weather, so I can't speak to that. You seem to have put a lot of thought into your trip, and as long as you are aware of the drawbacks of being in a more isolated area during part of your trip, I'm sure you will have a great time.

I have been to Florence an Rome many times; have been there on day trips and several multi-night stays. Have been in Florence in twice in April -- that is the nearest to winter time. My recommendation is to skip the countryside stay at Castello di Casole and save it for another (spring-summer-fall) time frame. My experience is that few people visit Italy only once.

I would stick with Florence and Rome. While, as I said, I have visited neither in winter, they are large cities with varied interesting venues for exploring and great restaurants.

And it seems to me that being somewhere that a car is not needed might be helpful given the short days and potentially icy roads.

That being said, enjoy your trip!

I'm sitting in our Florence apartment, at the moment, looking at the Ponte Vecchio, and the rowers on the Arno. We just arrived here, after a week in Rome. We have three thirty-somethings with us, and they are finding an extraordinary amount of things (including many non-checklist things) to do ... despite a lot of their friends warning them that we had scheduled way too much time in each city. We have been enjoying unseasonably warm weather but, if winter comes before we go home next week, there are an unlimited amount of good indoor options. (Also many easy day trips by bus or train from both cities.)

We did rent a car, and drove around for a few days. Not the first time, driving in Italy, but it never gets any easier. The countryside was okay at this time of the year, but is already starting to look bleak. Gets dark crazy early, so it's not the same experience as leisurely countryside exploring in the summer when it doesn't matter if you get lost. Best thing I can say about the driving experience is that the ham and cheese sandwiches in the autostradas are most excellent ...

I am about to make my 5th return trip to Tuscany, my third time in Dec/Jan, and there is so much misinformation in the thread, I just had to sign in and say something!

Tuscany is mainly green in winter. Right now, the winter wheat and other crops have not appeared, but you can look at these pictures and see for yourself it is green. I didn't take these pictures, but a woman who posts all the time on Slow Travel took them, and she has lived in Tuscany all her life

http://www.athomeintuscany.org/2012/01/31/tuscany-in-january/

Tuscany has many beautiful historic countryside villas and palazzi. There are part of the history of Tuscany. The Tuscans were once the bankers to the world. There is nothing inauthentic about staying in a beautiful, special villa in Tuscany, or going some place where there is a spa. It is an historic part of Tuscan culture to do this.

Tuscany is not the land of flea markets. It is historically a place of artisan craft and very expensive handmade goods.

No matter what time of year you visit Tuscany, if you go out to dinner, you have to drive home in the dark. Dinner in Tuscany begins at 8pm and lasts several hours. It is much smarter to stay someplace where there is a restaurant, and if you want to eat a farms, it is better to go for lunch. At night, you can have a lighter meal at your hotel and drink as much wine as you like.

While you do need to be careful driving if it is rainy or below freezing, it is easier to drive in the dark on many Tuscan roads at night unless you have night-vision problems because you can see headlights approaching and coming up from behind you. Most Tuscan roads are no harder to drive at night than during the day, and at night there is very little traffic so you can go as slowly as you like.

I have had to change my driving plans when visiting Tuscany in winter because of snow or rain. Someplace like Volterra can get snow even when Pienza doesn't. But I have had to change my plans because of spring or summer rains as well. There is much to love about Tuscany in winter -- the smells, the colors, and the food. I also like that it is much less crowded.

But right now, I am having a very hard time finding the kind of special castle or palace stay I am looking for as a special holiday treat. That is because all these places are booked solid. (This is a spur of the moment trip.) But the fact that all these lovely places in the country are booked up for Christmas and New Year's ought to give you some indication of how popular it is to go to Tuscany and stay in a marvelous setting in the country when it is cold.

I don't post all this to persuade you to go to Tuscany instead of Paris. If you are having second thoughts, my suggestion is that you ask yourself how you will feel if you get to the Tuscan countryside and it snows heavily, and you cannot go anywhere until the snow is cleared. If you think you will kick yourself for not paying attention to your inner voice, then you should follow that inner voice and go to Paris. If it turns out Paris disappoints you in some way, then you can cross it off your list and come another time to Tuscany.

Since I posted the link to tips and photos on Tuscany in January, I thought I should post another link from the same blog with photos of Tuscany in December, so you can see the green, and know more about the weather, driving, Christmas and restaurants (many many are open at that time of year)

http://www.athomeintuscany.org/2011/11/14/tuscany-in-december/

Moving within Florence DZ. It has been suggested that you need to use taxis. I can also recommend the incredibly narrow buses that do the rounds. They seem to keep good time despite the lack of space. Finally you could hire bicycles to get around while there is also a segway tour of town (though the website is rubbish)
http://www.italysegwaytours.com/default.asp?lang=en

I've watched this thread with a chuckle and I'm curious how many of the contributors have actually been in Tuscany in December. We stayed in Florence for 5 nights and Montepulciano for a week in early to mid-December a couple of years ago. It was wonderful ! Walked into any Florence museum without reservations including the Uffizi, cruised the markets and highways without traffic. Experienced a variety of weather including sunny and warm as well as drizzle and cool. The landscape was strikingly beautiful with the above mentioned winter wheat emerging and covering the rolling hills of the Crete Senese with a velvety carpet of soft green along with the usual Fall colors in the forested areas.

As was pointed out to me by a winery owner, the Tuscan food is most appropriate for the season--heavier with rich pasta sauces, truffle and chestnut. The wines complement the cuisine as well with the dark hearty reds. I would definitely call ahead to any winery I wished to visit but their hospitality is still present and they have time to give it to you. We enjoyed the reduced commercialization of the season--it was less garish in the decorations with real natural fruits in the cornucopias placed on the walls, real greens for decoration, small bright blue tinted lights and no overbearing Christmas music droning on.

We had a splendid time and would return if we didn't mind missing the family traditions here at home. You will feel like you have the countryside to yourself. BTW--this was probably our tenth trip to Italy but our first in December.
Have fun--Paul

i've no intention of trying to dissuade the OP from staying in Florence at Christmas - in fact I think that would be far preferable to a whole 5 days at the resort they have booked, for which I would suggest 3 day max.

macanimals - I think the difference is you stayed in towns that had things to do and choices of restaurants at night, not somewhere remote.

I also understand the blog promoting winter in Tuscany since it's by a B&B owner. I'm sure they don't have much business that time of year.

I love Florence in winter. it is the only time in recent experience that it wasn't packed to the gills.
Although we DO like countryside, I think cities make much more sense in winter. The resort experience will be a resort experience. I think it would be very very boring after a couple of days.
Days are short in winter, so driving easily is limited.
Again, I concentrate on Florence.