Overwhelmed by Tuscany

I would suggest that you check "mappy.com" for driving times and distances. It has really been helpful for me in the past. The roads in Tuscany are winding and narrow in a lot of places and as I'm sure you've read, parking can be a problem too. Barb

Whitney, I understand completely when I think back to planning our last trip. We spent a week in Tuscany home based in a farmhouse for a week. I spent a lot of time on google maps plotting out the distance and time (time is more important due to windy roads) between a potential place to stay and the hill towns /wineries that we wanted to visit. For us, 45-60 minutes was the max we wanted to drive one direction to see something. We also wanted to be less than 5-10 minutes from a town where we could go out to eat. Lastly, I made sure the the place to stay wasn't so far off the beaten path on a windy road where it would take 20+ minutes just to get to a main road.
We ended up in a small town about 5km from Cortona. We took the train into Florence twice. It was about 30 minutes to Montalpulcino (loved the wine), 45 minutes to Siena, and didn't get to Chianti region until the last day on the way to the airport. We loved Castelli di Verrazzano and had a great lunch overlooking the vineyards. What a way to end a vacation. In April we are heading to Tuscany again, this time we'll see the hill towns we didn't get to last time, San Gimignano, Volterra, Montelcino, and Orvieto.

whitney, That seems like a bit of an "ambitious" number of places to see in a short 3-4 day time frame. It may be feasible to visit them all, but how much time will you have to spend in each one? If you visit Montalcino, I would highly recommend dinner at Taverna del Grappolo Blu. The food is incredible (best Bruschetta I've ever had!). Most hotels and other lodgings in Italy provide breakfast. If you're planning to stay in an Agriturismo or similar, there may not be a lot to do in the evenings. One very important point to mention regarding rental cars in Italy is that each driver will need the compulsory International Driver's Permit, which is used in conjunction with your home D.L. Failure to produce an I.D.P. if required can result in fines on the spot! You'll also need to be vigilant regarding the dreaded Zona Traffico Limitato areas which are becoming more prevalent in many cities in Italy (especially Florence). If you inadvertently pass through ZTL areas, you'll receive some expensive surprises in the mail several months after you return home. Happy travels!

Castellina in Chianti is about 5 miles "back in the country", which is not very far. The roads into Castellina appear to be pretty crooked, especilly from the west. We stayed northwest of Poggibonsi, as the roads are a little better. Better amenities like grocery stores and restaurants are available over there. Siena is centrally located, but I found the city difficult to drive in due to congested apartment complexes and difficult parking. It may be easiest to park out and take a bus into the city. We preferred other hilltop cities to the west including San Gim. and Volterra. Someone mentioned Orvieto, which we also loved. But it's just north of Rome in a different region. Farms in Chianti and much of Tuscany are relatively small. And they've discovered that tourism is a great secondary source of income. Virtually every farm has apartments or rooms for rent, so there's never any shortage of accommodations in the region.

Thanks very much for the replies! I've been trying to edit my original post for days and I keep getting error messages :( If you have any recommendations for areas or regions of where you stayed, those are most welcome as well. I don't really want to stay as far south as Orvieto. I will check out Poggibonsi--thanks David!

whitney, Your original post is fairly long, so if you've been trying to add to that, you may have run up against the text limit. That may explain the error messages. You may only be able to modify your original post if you don't increase the number of characters already there. If in doubt, just add a new reply with new information. Cheers!

Thanks for the help and advice, Ken! I did 't see your earlier response. I was trying to delete words from my post but oh well! We will do a bit more research to ensure there is nearby nightlife and be sure to get an international DL!

In 2003, we were staying in Siena and had gone to Florence for a day. We were trying to come back on the superstrada (highway) but ended up on the slow road that winds through the hille of Chianti. Best travel mistake we have ever made. The drive between Greve and Castellina is beautiful. We kept stopping to take pictures and stopped in Casellina and enjoyed a bottle of Chianti (just a glass, but took the rest of the bottle with us) When we went back in 2008, the first thing I told my travel companions is "we are staying in an Agritourismo in Chianti. We chose this one: http://www.greve-in-chianti.com/casanova.htm We chose it because we could walk into Greve and could catch a bus into Florence. Wow. What a great experience. Upon arriving, my sister asked if we could just cancel the rest of our reservations and stay there for the rest of the trip. (No) The town you have chosed is beautiful. Visitng Greve, Panzano, and Siena is very easy. Montalcino is a little farther, but very doable. I think you have chosen a great location given what you want to see. I have not stayed at the place you are staying, so can't comment on that. If you are there on a week end, Greve has a market Saturday morning and Panzano on Sunday (at least they did in 2008) We went to the Greve market and loved it. Also, be aware of the speeding cameras. They are all over small roads in Italy and the main road through Chianti is no exception. Just go the speed limit and you will be fine. (We never got any tickets and saw camera everywhere) As to whether you will be able to do everything on your list...only time will tell. We had some things on our list we did not get to...but that was because we SO ENJOYED the things we were doing. No regrets! Enjoy your trip. (I wish we were going again!)

You can do Panzano, Greve and the Castello di Verrazzano in a day from Castellina with time to spare. Then another day you can do Montalcino, Montepulciano, Pienza etc. Siena is closer (less than 30 min. from Castellina), but will take the better part of a day to visit. There are lots of spots to visit in that area, and the sky is the limit. One day you could devote a tour to San Gimignano and Monteriggioni, for example. If you feel up to it you could add Volterra as well and do all three. From Castellina to Volterra is less than one hour drive, a few minutes more if you want to swing by San Gimignano on the way there. Then you could do Monteriggioni on the way back to Castellina. There are plenty of restaurants all over the place in the Chianti. Every single village (and in between) will have some. This is the complete list:
http://www.ristorantichianti.it/