Tuscany & Umbria

San Gimignano, Montepulciano, Pienza, Assisi, Orvieto. First 3 can very easily/quickly be reached by bus from Siena. Just be aware of bus schedules for your return to Siena.

The last time we were in Siena, we did two day trips. We drove and didn't have any problems with directions or parking. The first was a long day - both Volterra and San Gimignano. The second was to Assisi. It was also a long day but an absolutely beautiful drive. Be sure to leave enough time to enjoy Siena. It's a wonderful place.

read thru a guidebook such as Rick's and see if there are any towns with sights that catch your interest. Also there are several TV travel shows (Samantha Brown, Rick Steves, Rudy Maxa, etc.) that will show you sights in some towns that can help pique your interest in a particular destination.

My wife and I really enjoyed Voltaire and San Gim (sp). We stayed over near Cortona and drove to Siena and several small towns in a loop. Driving was easy although the Italians have no problem with passing at any time. So just be careful.

I've been reading too many guide books -- I think I'm over-thinking the area. I'm pretty good at not feeling like I have to see and do everything. However, I'm really struggling with narrowing down Tuscany and Umbria into 2 day trips out of Siena that are relaxed, not too fast paced. I'm just trying to throw the dart on the map with other's suggestions. I appreciate all the input.

Without a doubt, I would (and did) go to Assisi and San Gimignano. The latter is far more magical after the tourist buses leave (watch the sunset from the ruined castle on the hilltop).

Darren

Rachel, I think I see where you're coming from. Reading the guidebooks and it sounds like every place has something interesting, and its hard to choose. So I'd recommend two things. First is to make a short list of things you'd really like to see. Some people might want to see wineries, some old churches, some are interested in local crafts, etc. After reading thru the books you have a good overview of whats out there; now make a list of a few things you'd really like to see/do and then find some towns that have it. If you want a more relaxed place, try to pick ones that tend to be closer together so you're spending less time riding buses & trains.

Second is to realize that you can't see/do everything. Perugia has nice churches, so does Cortona, Assisi, Orvieto, Spoleto (really impressive, actually) etc. With 3 days you can't see them all, but you can see 1 or 2. I'm not exactly saying that places are interchangeable, but for a tourist to some extent they are. And for every poster here who loved San Gimignano, there's probably another who found it a tourist trap and prefers another place; point is there is no perfect list that can be created to universal acclaim. So when you've figured out the top things for you and found places that have them, you're done!! Go and you'll have a blast.