I'm having trouble deciding on the best town to serve as my home-base in Tuscany. I've narrowed it down to Siena or Montepulciano. From reading this forum and travel books it sounds like Siena is much larger with lots to see and do, but Montepulciano is more quaint. I'm leaning towards Montepulciano because it sounds like a better place for strolling or relaxing with a glass of vino, but I'm worried that we'll miss so much of Siena with only covering it in a day trip. Any thoughts on these two cities?

Lucky you! These are my two favorite spots in Tuscany. Of the two, I'd suggest staying in Montepulciano as I think it will be far easier to get in and out of. Parking in Siena can be a nightmare. When you do park in Siena look into the parking just outside of twon listed as Campo parking. You will have a 7-10 minute walk max into town center. One of my morst savored travel memories is strolling through Montepulciano at twilight.

What time of year? Will you have a car?

We spent two weeks in Montepulciano and regularly ventured to Siena for dinner, and aimless wandering.
We love both places, but Montepulciano has my heart for the place I'd rather "live" versus the place I'd rather "visit."

I'll be in Montepulciano in a couple of weeks, staying for a week in an apartment -- taking day trips -- one to Siena. I'll let you know when I return my thoughts/opinions of the two.

Thank you for the replies! I should have specified that we'll be there in mid September with a rental car.