4 nights in Florence or 2 in Florence / 2 in Siena

Daytrip to Orvieto/Civita di Bagnoregio sounds great. I love Siena but you could make it a daytrip from Florence, since there is so much for you there, and save doing a one/nighter in Siena. I would not drop Florence down to two nights, but it depends on what you like.

Emily, IMHO, you really don't have enough time to see everything in Florence and a lot of Tuscany. A big question I have is how much of Florence do you really need to see? You can easily spend the 4 days touring everything in Florence. For Siena, you can easily take the SITA Corse Rapide bus (non-stop) from Florence to Siena and spend a nice long day there. With this day trip by bus, you really won't get a chance to see much else of Tuscany. Or, you can rent a car in Florence (with great caution of the restricted ZTL zones) and you can see a bit more. Just park outside the city walls of any town you wish to visit (ZTLs inside the walls). You might be able to hit 3-4 on a long day trip.

Most people don't realize what a time waster changing hotels is.

In the time it takes to pack your suitcases at the Florence hotel, check out of the hotel, check in and register in another hotel in Siena, unpack your suitcases, put things away, you can travel from Florence to Siena and back on a day trip. Siena is just over one hour away from Florence. Most people in California commute farther than that on a daily basis.

You should choose. Either you stay in Florence the whole 4 nights. Or you rent a car for 4 days and stay somewhere in the countryside in Tuscany for the whole 4 nights. Splitting your stay into 2 hotel locations is a time waster.

I've been to Florence twice, each time spent a full week. The first week, I didn't go on any day-trips and thoroughly enjoyed seeing the Major Sites in Florence. When we went the second time, I seriously considered spending the whole week in Siena, because I'd heard so much about it, but we ended up staying in Florence. We did a day trip to Siena, and honestly, both my friend and I, just "didn't get it." We were so glad we decided to stay in Florence. Don't get me wrong, Siena IS beautiful, but there aren't as many places to see as there are in Florence. Make sure you have at least one late night sipping wine in the Piazza della Signoria in Florence. When I was there, there were acapela opera singers, guitarists, etc., the fountains lit.........Oh how I love Florence!

Regarding seeing the countryside in Tuscany: You may want to do an all day wine-tour. You can google this or look on Trip Advisor. This will give you a nice ride through the countryside. Your hotel may also be able to advise you on this. I am sorry, I don't have that info with me at this time.

Thanks everyone for the quick replies! This confirms that we should stick with what we were originally planning and stay all 4 nights in Florence. I was looking at the map of all the hill towns in the latest Italy guidebook and he has the drive time between Florence and Siena at 2hrs but sounds like that's conservative? From my initial reading it sounded like more of the wine areas in the region were closer to Siena and I didn't want to spend all our time in the car, but I generally agree that changing hotels is a waste of time and takes away from the relaxation of the trip. It sounds like a well organized day trip or two would allow us to experience the smaller towns and leave us a reasonable amount of time in Florence.

For Florence, we plan on hitting Accademia, Uffizi, and the Duomo for sure but I'm more interested in wine/olive oil/cooking experiences here combined with some time to wander. I'm not a huge museum person - would rather people watch - and we'll be doing a lot of those during our days in Rome. My husband is the museum buff but he's been to Florence before (Rome too). Definitely jotting down some of the other recommendations in this thread for our more detailed planning.

I second the the recommendation to check out day excursions from Florence. We spent a week in Florence as part of our last Italian trip in 2010. Three of us ended up doing a full day wine/cooking excursion that we really enjoyed. It included a beautiful drive (6 people total), wine and olive oil tasting at an estate, and then a pasta making lesson followed by a terrific al fresco lunch in the country that included fresh chard quiche and unbelievable tiramisu plus the fruits of our labor. Our driver was an opera singer and we were serenaded while we rolled our ravioli. After being the lone driver in the group for the previous two weeks (due to a forgotten driver's license), it was nice to sit back and be a passenger for a day. The outfit is Accidental Tourist.

Thanks LeAnn! That sounds amazing! Definitely going to look into what they offer.

Just a note on moving from one hotel to another and how long that takes: I pack my carryon the night before. The clothes for the following day (travel day) are laid out. The carryon is zipped up. In the morning, sleepwear and toiletries go into either the daypack or the front zippered compartment of the carryon. Walk out the door, check out, the whole process usually takes ten minutes. At my destination, after checking in, I unpack what I need for the remainder of the day into my messenger bag, go out for the day, and unpack the carryon when I return that evening (and I'm in for the night anyway, so unpacking or packing is not time wasted or taken from sightseeing hours). The only time moving takes up is actual travel time from city to city, plus a few minutes the morning of travel day. Travel time (except in tunnels) is, for me, part of the journey - who knows what I'll see from the train or bus window?