nytraveler

You don;t want to rent a car but you want to ride a Vespa????? Do you have a death wish? What do you think it would be like driving narrow, twisty country roads in chilly wind and rain or possibly fog on a bike you are not familiar with? (You have looked at the average weather haven't you?)

It's possible to see quite a few towns by train (but check schedules carefully) - but to get out into the countryside you really need a car. Granted there are buses but they are few and far between - really for locals - with perhaps 1 or 2 buses in each direction per day for many towns.

dreamon

I would decide which towns you want to visit and then see whether transport is available. Otherwise it's too vague as transport varies so much.

In some cases, bus services are infrequent (or non-existent) but in others they are quite often, sometimes with a break in the middle of the day. Last year we had a week split between Montepulciano and Siena - with a few day trips by bus - that worked perfectly fine for us.

isabel

Given the time of year and amount of time I would just choose either Siena or Orvieto (possibly both). They are not 'tiny' hill towns, but they are towns on hills and around the edges they feel and look very similar to the smaller hill towns. And they are not cities like the size of Florence so even in the centers they have a somewhat small town ambiance. There are plenty of walks you can do out into the contryside if you get a nice day that will give you the 'Tuscan countryside' feel.

From Orvieto it is possible to visit Civita di Bagnoregio by bus and that IS a small hill town (www.pbase.com/annforcier/image/161278352). I agree with 'always have a Plan B', in my case for the day trip to Civita it was to get the earliest bus there so I was aiming for a mid day bus back, if I missed it there was still at least one more. Also, the distance between Orvieto and Civita is not that far so worse can scenario would have been a taxi).

Here are some other photos taken from Orvieto and Siena which show how close to being 'in the countryside' they are:

www.pbase.com/annforcier/image/161278309
www.pbase.com/annforcier/image/161278312
www.pbase.com/annforcier/image/161276959
www.pbase.com/annforcier/image/161277006

Lots more photos of both Siena and Orvieto in those galleries.

Dukey1

Vespas are great UNTIL it starts raining. Look at my profile picture and no that is not a Vespa.

bvlenci

I see that KYBourbon is right, that the first bus from Siena to Montepulciano is in the afternoon, so you would have very little time there. The schedule is obviously set for the benefit of students who travel to Siena in the morning and return home in the afternoon. The last time I checked the timetables, there were more possibilities.

The good news is that there are many more possibilities from Buonconvento, and since you're interested in small towns, that might be a better base. Also, the travel time between Buonconvento, Montalcino, Pienza, Montepulciano, and Siena are all less than an hour by bus. Finally, Montepulciano, Buonconvento, and Siena (but not Pienza and Montalcino) have train stations, so you could do some of your traveling by train. However, Siena and Montepulciano are on hilltops, and their stations are down in the valley. In Siena, there's an escalator that takes you up to the town, but not very central. There are city buses that connect the escalator to the center of town. From Montepulciano station, you'd have to take a taxi into town, and I don't know if you can rely on finding one. I'd much rather take the bus to Montepulciano.

As I said, I've never been to Buonconvento, but on Google Maps it looks as though the train station is in the center of town.

I can assure you that the buses that go from town to town (extra-urban buses) are more comfortable than city buses, and they don't make anywhere near as many stops.

bvlenci

I'd like to address a previous point. The buses that serve small towns in Italy are, as I said previously, are mainly used by students. Believe me, they're not going to leave students stranded on their way home from school. They're not allowed to strike during hours that students are using them. There can be other risks, such as being misinformed about the location of the bus stop, but you don't have to worry about strikes. I would suggest that if you're going to be based in a town, it's a good idea to scope out the bus stop locations before your planned day trips. This is another argument in favor of Buonconvento as a base, because the bus stop is at the train station.

NYCFoodSnob

Buonconvento is a nice, flat, small town with a historic center. Most tourists never heard of it, but many drive through it on their way to Abbazia di Monte Oliveto Maggiore. The heart of the old city is where Via Roma meets Via Soccini. The train station is on the east side of the SR2. The distance is walkable. I suspect the town in December is quite quiet. It gets the most traffic in summer.

The countryside around Buonconvento isn't particularly special. Standard fare for Tuscany. Things get much more dramatic on your way up to Abbazia di Monte Oliveto Maggiore, where the landscape turns amazing. The long, local drive from Abbazia di Monte Oliveto Maggiore to Montepulciano offers serious postcard visuals. I don't recall seeing or passing any buses along my favorite route.

San Gimignano is a fun city to stay in and explore, and it's fairly easy to get to via public transport. It's countryside is spectacular. The sunrise vistas from Viale Roma are incredible, and the cappuccini and cornetti at Caffe' Giardino, all made in-house, are among the best in Italy. There are numerous spots on the outer edge of San Gimignano that offer postcard picture views.

The very popular Monteriggioni is a fairly short distance away. Siena is about a forty-minute drive from San G. A lot of people without cars hire private drivers for these close excursions.

Volterra is not far from San Gimignano, southwest. It, too, offers plenty of countryside vistas and is a fun city to visit and explore. It has a strong mix of local and tourist life all year round.

Have no idea what bus transport is like to these areas, but I suspect service is available. I would not hesitate to contact the tourist board in each and ask your questions. "Official" information often differs from what you read on travel boards.