What town to stay in Tuscany

Melissa,
Siena, and Lucca to a lesser extent, can be tough with a car because you have to park outside the walls. Consider an agriturismo, an apartment on a vineyard, for both more space and easier parking.

This will give you some ideas for southern Tuscany http://www.slowtrav.com/italy/tuscany/hs_planning.htm

A lot depends on what you like/want. Staying in a hilltown can be a fun experience, especially at nite when the crowds depart. In some you can park within the town walls if you have a small enough car to fit, in others you'd need to leave the car on the street and walk to it (typically not too far, though). Staying outside of town means you can't walk in the evenings to dinner, etc. The flip side is a more relaxed place to stay, probably quieter, and perhaps with some great views depending on what you book.

Take a look at a guide book to get more ideas about what options are available to you.

Melissa, my answer is based on my own experience. Do you like to have wine or a beer with your meal? If so, stay in a town. Driving at night is confusing enough without adding alcohol to the mix. We really enjoyed staying in an agriturismo, but could not have wine with our meals because of the drive. Enjoy. Jeff

We met a number of American's who had the same experience as Jeff...staying at an Agritourismo is one way to experience Italy...but for me, you can't beat the experience of staying in the towns or city centers...the evening passeggiata makes you into an Italian....if only in spirit...you can't do that in the country. As to where to stay...you can't go wrong with 3 nights in Florence, 2 nights in Lucca, 2 nights in Sienna (with day trips to San Gimignano and Multepulciano) and 5 nights in Rome (or maybe a night in Orvieto and 4 nights in Rome).

We've stayed in Siena and Montepulciano. I highly recommend Montepulciano, it's wonderful.

Susan, what did you see or do in Montepulciano that made it special to you?
Cause what ever it was, I guess we missed it.

I can recommend Lucca and the Hotel Melecchi. The Melecchi is just outside the town walls and has its own gated parking lot. We stayed there with our small child and were treated very well by the family that runs it. You can walk a block and stroll the largely car free center of town. It's quieter and less hectic than Florence. On top of the walls are a series of parks. You can day trip to Florence and Pisa by train. Lucca is easy to get into and out of by car.

I would center yourself in Siena (Avis avail there)or close by. That way you can rent a car(great for baby) to see hilltowns nearby easily. Lots of good things to see and very close to Siena ie. Pienza, Montepulciano, S Gimignano, to mention the best. And also if you still have more time you could see Orvieto, Cortona. Lucca is nice to pass thru like Pisa but not for 4 nights. 4-Florence, 4-Siena, 4-Romne is a great plan.

With a baby, you migh tlike to stay in apartments, for maximum mealtime and nap flexibility (and more space for you and the child).

I found our Lucca apartment (inside the walls) on this website:

http://www.knowital.com/tuscany/accommodation/

some rent only by the week, but many others do 3-day minimums instead. It never hurts to ask if you see one you like, even if they only list weekly rates.

Four nights each in 3 places (Florence, Lucca/Siena, Rome) would be good.

I was going to suggest Hotel Athena in Siena, easy because it is near St. Marcos Gate and includes parking, but you have a baby, and the hotel is a bit of an up hill walk to the city center. Far enough that I don't think it would work for you. The front desk at Athena has everything you could possibly want though, so maybe they can figure something out for your special situation. This is a full service hotel.