We will be spending 8 days in Tuscany in January...two or so days in small town(s) and the rest in Florence. My tentative plan is to rent a car at the Florence airport upon arrival from the US and drive to one town where we will stay one or two nights. Then, en route to Florence where we will drop off the car, we could visit one or two other places. My idea now is to have the first place be Montepulciano; should we spend one or two nights? And then visit San Gim en route to Florence city? Or do one night in Montepulciano and one night in San Gim? Any critiques or suggestions are most welcome. We have both been to Italy before; I have spent a week in Florence recently but partner has never been to Tuscany. I should add that we are very interested in food and wine but not so keen in visiting a winery. What we like best is to walk the streets of a place and soak up the atmosphere.

If you only have two days in Tuscany, I'd spend it in one location to take advantage of the relaxing nature of a trip like this. Rushing from one accomodation to another, packing and unpacking, would interfere with your enjoyment.

Stay in or near Montepulciano for at least two nights. With a flight from the US and the drive from Florence, you'll want time to unwind. If you have one more night to spare before you need to be in Florence, then I'd spend it near Greve or Radda in Chianti rather than San G. which is far busier.

You can drive quite a distance from both those locations for completely different experiences on day trips.

Thanks. I think I will take your advice and stay two nights in the same town. Do you have any hotel recs in Montepulciano? I limited the countryside portion of the trip to two nights since I think I would like to have the six nights in Florence. Maybe we could visit Greve or Radda on the way to Florence, after Montepulciano. Give San Gim a miss??

Six nights in Florence would be too much for me. I think Tuscany would be worth at least 4 days, then 4 days in Florence. You might consider 2 days in Montepulciano, and 2 days in Siena, exploring both of those areas and small towns in the area.

You may be right. We actually have only 7 nights, not 8 as I originally posted. But since I spent a week in Florence two years ago, I am now thinking:

Pick up car at Florence airport upon arrival.
Two nights Montepulciano
Drive to Florence, visiting Radda or San Gim en route
Four nights Florence
Train to Bologna mid-day
One night Bologna.
Fly home from Bologna via Rome or Milan

Good plan? Remember it will be kind of cold so cities will be better than contryside, I think.

Siena is a city, though small, and definitely worth a visit if not a stay nearby. It's quite beautiful and you can wander the streets, sit in a trattoria or see the sights.

I haven't been to Bologna or Milan, but love Rome. With only 7 nights I'd choose the Montepulciano/Pienza area for 2 days, 2 days in the Siena area and the rest in Florence or Rome.

There have been some recent threads about accomodations around Montepulciano if you have a look through discussions. We stayed outside Siena and did drives around the countryside from there.

Having been to Italy before, you likely have a good idea what you want in terms of amenities and budget so when you finalize your itinerary, you can probably narrow down the accomodation search.

Thanks. We have spent lots of time in Rome and will not visit on this trip.

I would just suggest that you don't miss Siena. If you have a car, it might be better to stay outside of the city walls where they have easy access and parking and walk into town, as it's certainly not a town made for driving (as is true of most European cities). But it sure is a place not to miss.

You know I am not sure why I am so resistant to adding Siena..maybe cause of the difficulty of taking a car into the city. (I did go there many years ago but hardly remember it.) Also it does not have a good reputation for food. I should add that this will not be the last time we will visit Italy. But it is all food for thought, so to speak so I will consider. Would love to read recs for hotels in Montepulciano.

Having just come back from a month in Italy I would encourage you to visit San G as it is unique. Best to visit early morning or late afternoon to be more comfortable. I stayed on a vineyard just out of San G for a week and it is a great base to visit other really interesting small towns like Colle di Val D'Elsa, Greve, Radda , Volpaia. You also must visit Sienna. A word of warning - Florence is hopelessly crowded with tourists, a couple of days there might see you out.

We just spent a long weekend in Tuscany, in the Chianti region. What a gorgeous area. I agree with the other posters on shortening the time in Florence. I loved Montepulciano b/c of the atmosphere, the winding, hilly streets and the nice people. PLus I bought some of the most marvelous truffle honey there.

Anyway, Siena is not my favorite either. Maybe b/c of the size. I really like your idea of visiting Bologna. On our drive home, we stopped by for an afternoon and it is definitely on the return to visit list. It is a vibrant, working city that is so clearly not dependent on tourists. The food is supposed to be fabulous as well and b/c the streets are covered walkways, the weather won't have such a huge impact on the visit.

Am now considering adding Bologna at the end of the trip in January. We could drive to Montepulciano and stay two nights. Visit one or two towns en route back to Florence, Drop the car in Florence and spend 3 nights there. Train to Bologna and two nights in Bologna. OR four in Florence and one in Bologna. Would love hotel recs on Moonttepulciano and Bologna. And critique of my plans! Hotel budget is about 250 dollars a night if possible in hotels with character in good locations.

THANKS to all..more advice?

Haven't stayed in the Montepulciano area, but I've read recommendations from others here and elsewhere for both
Relais La Chiusa (www.ristorantelachiusa.it)
and for Villa Cicolina (villacicolina.it).
I am always looking for the next wonderful place to stay when in Italy.....

I loved Siena, its Duomo, the tower and the Campo. Do not miss the Duomo, one of the most ornate I ever seen. San G is very unique, you must try to climb the towers to see the town from there. Montepulciano, Pienza, Cortona, Montacino, Radda and wine towns are all nice, but to spend a night seems too much. We visited 2 or 3 towns a day. May not have gotten to know it as well, but I got a good idea. While in Florence, I highly recommend the Pensione Bencista run by the Simone family in Fiesole, a 10 minute bus ride by bus (very close to the Bencista. You feel like family upon arrival. The included dinners are good, but nothing fancy. I wish the dinners were not included so we could have tried various restaurants in Florence. Anyway, we had a car rented in Florence and drove down to Siena and used that as a base to see Cortona, Pienza, Montalcino, Montalpulciano and others. Then, drove up to San G on the way back Florence (Fiesole) and used that as a base to see just to the south of Florence, the Greve-in...towns, Radda, Castella, and north and east of Florence, Pisa and Lucca. My point is, all these towns are great but to spend 2 nights at one when you can see others.... I am planning a trip to Rome in late Jan or late Feb. Do you know the real life temperatures will be at that time of year? And the rain, a lot or over hyped?