My partner was offered the use of a villa in Castellina in Chianti (between Florence and Siena) and we've decided to accept this generous offer and to spring for a dreamed-of two weeks in Italy, arriving Fri March 29, leaving April 11, taking my 16 year old daughter with us. Being three introverts, we love art and cities but need to chill out in between bouts of intensity. Considering this, and considering we are on a budget, I'm seeking suggestions to maximize this free home base, wondering if it sounds reasonable to (with our rental car) spend our first few days (including Easter) doing day trips to Siena, Assisi, San Gimignano, etc, mixed with picnics and walks/hikes; then make an early morning drive to Rome, parking outside the city, buying Roma passes, and staying near Pantheon for one night, sightseeing the whole next day, then returning late to Chianti, then more countryside hiking and relaxing (possibly up to Cinque Terre), then Florence. We would be splurging on the Rome hotel so would rather not stay over in Florence, but would it be crazy to just go twice, each time for the day?--it wouldn't have to be two days in a row, even. Thanks so much for any advice.
There's no reason you cannot do day trips into Florence. You're just going to be approx. 28 miles south of the city. See to see if buses are available from Castellina, as you wouldn't have to deal with ZTL's or parking. Don't forget to see Volterra, which is another great hill top city. It's just southwest of San Gimignano.
FYI: You'll be staying a few miles east of Poggibonsi. There are two great supermarkets/food stores there. A good place to park your car on the way to Rome would be Orvieto. It's another great hilltop town, and an easy drive south of where you'll be staying via A1 (controlled access highway.) Orvieto is a 70 minute train ride into Rome Termini.
From Castellina to Firenze, by car, it's about 25 miles, less than 45 min. And a good portion it's freeway driving. Many Americans commute distances longer than that just to go to work on a daily basis. Just drive to Piazzale Michelangelo, on top of the vista point. You can park for free there all day. You can walk down to the city center in about 20-25 min. To come back up take a bus (number 13) or a taxi to avoid the uphill walk. It's very easy to drive to and no chance of entering the ZTL. Use google maps to see. Take a GPS navigator to Italy (load European maps in it).
David and Robert, thank you both for your wonderfully specific advice--I was wondering about supermarkets and it is greatly reassuring to have a very specific idea of travel times to Florence and parking options for there and for Rome. Our other big question, based on the above time frame, is whether we should try to get to Venice. We overdid it in Turkey two years ago, trying to see so much that we got exhausted...yet with the distances being a lot shorter in Italy, I may be being overcautious. We may not be back for a while, so if you think it wouldn't be too much, and there IS "one more thing" about each of you might say, "Ah, don't leave without going to _____", I'd happily ponder your ideas. And I ask that knowing that it might be like asking, "Which is your children is your favorite?":)