We are spending 3 weeks in Italy this October to early November. We have dedicated 8 nights of our trip to Tuscany. We are thinking of Florence, Chianti, Siena, and Grosseto. This is our first time to Tuscany and have no idea about location and how easy it is to get to each place via car.
Question: Should we spend a couple nights at different hotels in each place, OR stay at one awesome place centrally and drive to each place?

I've spent a couple weeks in Tuscany maybe 5 times in the past 20 years, doing it several ways. I'm now convinced that my favorite is finding an apartment within a town for a week -- in your case, I think that might be best -- or at most just two places. Two weeks from now we'll be arriving in Siena for a week in an apartment right on the "Palio" Campo --and really looking forward to it. Siena offers lots of buses (and some less convenient trains) for visits to various other towns or areas. And we'll get a car just for our last couple days there.

Previously, I think my favorite stay was a week in Montepulciano, but it is a bit far from places like Florence for full day trips.

I'm with NeoPatrick on this with one difference. We always stayed in hotels with staff around to help us and make suggestions.

Although we came armed with a list of "to sees", we always took a recommendation from a local to heart. We didn't get to Italy as often as Patrick so I think we might have "graduated" to an apartment at some point.

You could almost make Florence and Grosseto your 2 bases for the time/area you mention above.

TDudette, you have a pretty good point. I usually recommend a hotel to first time visitors to major cities in particular for that very reason. But in Tuscany, I've found it quite different. At our apartment in Montepulciano, we had the owner of the "villa" who was more help than ANY hotel employees I've ever run into. And we tend to be pretty outgoing. Some of our best recommendations come from the person serving us our coffee and pastries in the morning. Or from a waiter at night whom we ask "where is the NEXT best place to eat". Locals in Tuscany seem to be so willing to offer suggestions!

coordinatethis,
These may help
http://www.prolocomontalcino.com/en/...-of-the-thrush

http://www.slowtrav.com/italy/tuscany/hs_planning.htm

IMHO - we always stay IN a town. It's no fun having to forego wine with dinner in order to be able to drive back to someplace deep in the countryside. Or find a cab to take you there.

A house in the country makes more sense if 1) you plan on cooking dinners or 2) you plan on having a chef or caterer provide dinner. (May make more sense for a family group with small kids who don;t want long, later dinners anyway.)

With 8 nites I would pick 2 destinations and Grosseto would not be one of them.

i would pick somewhere between Siena and Firenze, in a small town incase you want to do supper and wine and not drive. from that location you can do most of the "to do list" within 1 ot 1.5 hr drive . ie, Siena, Firenze, Chianti region, Volterra, San Gimignano, Montalcino, Cortona.

i am assuming you want to drive, and not do the train deal.?

it is always hard to answer these questions, without knowing OP's budgets and likes, if they ok with 1-2 hr drives, etc. .

Ideally, I think we would like to stay in 2 locations of Tuscany, preferably at a vineyard somewhere. We could stay at one place for 4 days and drive south to another place for 4 days and explore the two areas. We love eating, drinking wine, exploring, and just relaxing. Your assumption is correct, we really do not want to go to a dinner and then have to drive an hour back.

Here is a website listing many agriturismi: [farms offering rooms and/or meals, often of very high standard].

http://www.agriturismo.it/en/farmhouse/tuscany

the disadvantage is that eating "in" might get boring after a couple of nights and then you have to drive to dinner, and what is worse, drive back.

which is why we like to do what nyt says and staying in a town or city.

In Chianti, you are very short walking distance to Radda in Chianti,with vineyard views from Relais Fattoria Vignale.

Near Grosseto is very good wine country. They produce the red Morellino di Scansano. Some very attractive towns in that area include Magliano in Toscana and the almost totally unknown Manciano. There are also lots of wineries, some with accommodations.

Good places in Tuscany to find wineries that serve dinner as well as their own wines are around San Gimignano (white Vernaccia mainly) and around Siena.

Personally, I don't need a hotel staff to steer me around Tuscany. It's all beautiful and it is fun to explore without pointers. As for staying in one "awesome place," if you like to do a lot of day tripping and a lot of wine drinking, you should probably switch locations as need be. Tuscany closes up during the middle of the day, and if you've drunk a lot of wine the night before and slept in, you can find that by the time you reach a far day trip destination, you can't get inside anything, and by the time it reopens, you are ready to go home.

If you do google searches for "Tuscany winery accommodations restaurant kitchen apartment" you can sometimes come up with just what you are looking for. You can get even more specific by making the search string "Chianti winery" instead of just "Tuscany winery" or try "Brunello winery accommodations restaurant kitchen apartment." Add the words "short stay" if you will be renting for less than a week.

I prefer having an apartment in Italy because I can't eat 2 huge meals a day and I like to make myself a cup of coffee in the morning without having to ask somebody for it or share my breakfast space with strangers.

for first time in Tuscana,as a couple, and into wine.... i would stay in a town. this way you can always go back, walk to osteria or ristorante , enjoy some vino and not worry about driving.

i am all for staying at diffent locations, especialy if only 2 persons.