Tuscany for 3 days: Better/cheaper to rent car or book tours?

You'd have to run some specific numbers. My car rental last year, with gas, tolls, parking, insurance, second driver fee, was about $100 per day for 5 days. You might be able to better than but not by much. We took a full day tour with Tours By Roberto, and that was 90 euros each, about $126, for one day. With 3 full days, plus your arrival day, you might do something like this: - Arrival day, arrive by noon, orient yourselves to Siena. See il Campo, the Duomo, wander, shop, eat - Day tour of Chianti (Tours by Roberto highly recommended. He will customize if you don't find what you want in his regualr offerings.) - Daytrip to Florence via bus, self-guided - Bus trip to Volterra and/or San Gimignano. You'd need to research this more, but I ran into a couple who did this via public transportation as a day trip.
- Departure day

Laurel is pretty close to right on the daily price of a short-term rental (those things really suck for somebody who's used to averaging twenty-five bucks a day for longer-term rentals). Tolls will be negligible and you won't burn twenty-five bucks a day in gas going to the Rickite hill towns (a bit more to Florence and back). Other than Florence, Volterra is probably the most distant place you'd go and it's less than an hour from Siena. The scenery is pretty good once you get off of the freeways. So, using Laurel's numbers, a car is half the price of a tour if two people are involved. I've never taken a tour anywhere in my life, but getting around Tuscany in a car is easy. I prefer to do my own reading rather than hiring a guide.

Thanks so much for the input. I want to visit Montepulciano, perhaps Cortona & San Gimignano so would doing it on our own with a car be feasible vs. by bus or booking a tour? Are there tours that cover a couple of small towns in a day? I have Rick's Italy 2011 book and he seems to lean towards having a car for the small hill towns.

Laura:
You could use the bus to go to Florence for a day, then rent the car for only two days to do Cortona, Montepulciano, etc. Maybe one day one direction -- north and west -- and the other day east and south. Then you only have two days rental, minimal gas, a little parking. Slow Travel has some wonderful day tour drives like this one, which is one of my favorites http://www.slowtrav.com/italy/tuscany/sd_driving_tuscany.htm. On that page, in the righthand column, you'll find links to many more driving tours.

Laura, there is a full day tour offered by artiviva.com, they are based in Florence, that does go to three hill towns, one winery for wine tasting and lunch. It is called "Best of Tuscany" and you can look it up on their website.

Laura, I would rent a car as opposed to a tour. However, for Florence, I would definitely use public transit. While you can probably visit some of the other towns via public transit, it will be much easier by car and you won't be restricted in terms of how long you desire to stay in each town, etc. We enjoyed driving ourselves and being able to stop on a whim if we saw something interesting or wanted to take pictures of something.

Thanks, all so much for the guidance. I think renting a car for 2 or 3 days is what we will do, plus take bus/train to Florence for a day. I want to absorb the small villages and countryside instead of doing "touristy" things. Any advice on where and how to do the car rental will be appreciated as well. I know this will be an unforgettable trip and can't wait to go!

Group trips are good for- -meeting other people. You are unlikely to chat to as many people if you hire your own car. -wine tastings. Italy is as strict as any country in Europe on drink driving. -going straight to the best bar/restaurant/castle etc rather than taking pot-luck When you take into account how much you would spend on car hire, restaurant, wine tasting etc tours usually work out about the same overall price as a DIY day with car. You may save 10-20 Euros by driving a car but not a huge deal. Go with what you feel will be more fun. As Marianne has kindly pointed out there is a tour called best of tuscany which does have many good reviews on Trip Advisor, and I'm sure you wouldn't regret a tour with Roberto. One to cast your eye over would be http://www.slow-days.com which seems to tick most your boxes. Hope this is of some help. Enjoy your future Italy trip!

As far as car rentals go, I had a great experience with http://www.gemut.com. They beat the rate both Hertz and AutoEurope quoted me, yet my car was from Hertz through AutoEurope. Go figure. Anyway, submit a request and then talk to Andy. They have 24x7 English support, too.

I always check all the rest and go with the cheapest, then keep a watch as they can go down... if they do, I make a new reservation. You might also try a variety of number of days, sometimes its cheaper for 3 days then 2, and if you can keep it a week that is usually your cheapest. I would pick up at the Florence airport and just head right to the freeway being careful not to get into the city, but its easy enough if you just pay attention. I have driven around Tuscany many times and find that I meet lots of locals as I do not arrive into town with a herd of other tourists. I am also free to ask advice of locals and just drive and see what is around the next curve in the road. I really don't drink more than one glass of wine and if I were visiting the vineyards a simple tasting is all I need, so drinking and driving is never and issue for me.

@Terry kathryn: It sounds like you are a bit of an old pro at touring Tuscany, however you will find that limits in Italy are stricter than in the US - http://driveandstayalive.com/articles%20and%20topics/drunk%20driving/artcl--drunk-driving-0005--global-BAC-limits.htm
-the carabinieri will politely listen to your explanation that you have been 'only tasting' not drinking and then go right ahead and test you. As for meeting the locals, when your Italian in fluent enough you will meet plenty. Beyond a certain politeness afforded all strangers, most residents are less than impressed by tourists expecting that everyone should speak a foreign language (English).

No one has remembered to mention parking fees! If indeed you can find a parking place in cities like Siena, Florence and in many smaller ones like Lucca, you have to park outside the city. So I would take the advice which recommends renting only for visiting villages out in the countryside.
I don't know if it works from the UsA as within Europe where if we pre-book from the country where we live, it is cheaper to rent a car than doing it on the spot in Italy or wherever. But you seem to have got some tips on that score.