OK, let's see what I can dig up:
Rome - if you do decide to get a taxi from the airport, make sure you take note of
Eagle's advice and only get a taxi from the official taxi rank. There is a set fee for the airport-city journey, regardless of where in the city, of Euro48 (might have gone over 50, it's been 3 years since I took a taxi from the airport). If anyone comes up to you in the airport, or just at the exit and asks you if you want a taxi, decline and move on. These are "mini cabs" or taxis without meters and will charge you far too much.
Empoli - there is a car park next to the train station, can't recall how much as it has been many years since I've driven around that part, but know that many locals park and ride when commuting to Florence during the week, so the car park fills up from around 8am.
For the towns you've listed to visit as day trips in Tuscany, you may find you can't see them all, but if you plot your journey and use the B roads (ie, not the highways) you'll have great scenic drives in between destinations.
As for
wineries, there are many (!), particularly in Montepulciano, Montalcino, Greve in Chianti. It depends what you want to taste - are you looking for Chianti Classico, whites, all of the above? On your visit to San Gim, there are two wine tasting places not far after you enter the main gate. The one on your right (look for the wine barrel and Vino sign) has a great terrace and you can taste the Vernaccia, a white wine local to San Gim only. In San Gimignano, there are some great Tratorrie (plural of Trattoria) and Gelaterie (plural of Gelateria) to be found. In particular, the gelateria in the Piazza Cisterna is the best one. It's on your left as you walk up the hill and into the square. He wins many awards and has a wall of famous visitors, so you know you're in the right place when you see the photos. And as for places to eat - they are all good, even if they are on the main street. Just look at the menu (stay away from Menu Turistica) and see if anything takes your fancy. Of course there are a few tourist-oriented ones on the main square (Pz Cisterna) but if you walk a few paces down any street off the square you'll find good ones.
While I'm on San Gim, I found some accommodation information in my notes which might help you:
Hotel Pescille -
www.pescille.it Good value at a rustic hotel only 3 km from famed San Gimignano with great views---100 to 130E
Hotel Bel Soggiorno – San Gimignano centre -
www.hotelbelsoggiorno.it/If you're after Chianti Classico (and why wouldn't you be?!!), then Greve in Chianti is the epicentre of all things Chianti. Handily, Panzano is in the Greve district...see below:
If you want to spoil yourselves with wine and meat, then a trip to
Panzano and a wander into Dario Cecchini's L'Antica Macelleria Cecchini (butchery) is a must. He's become quite famous now, as the Dante-quoting, meat-loving Tuscan butcher. He opened a restaurant across from his butchery called Ristorante Solo Ciccia (local dialect for "Restaurant Only Meat", ciccia = flesh, although they do have a Vegetarian menu now!). You have to book ahead for a seating, and there used to be two sittings - at 7pm and 9pm. Otherwise you can buy some specialties from his shop and take them back to Montepulciano to enjoy with your wine purchases if you prefer.
If you want to do a little tour around Chianti for wine tastings, then have a look at this site for ideas
www.chianticlassico.com/en For
Florence, Eagle's restaurant suggestion is a good one for Tuscan fare. You could also try my favourite, Dei Fagiole (to the beans!) which is on Corso dei Tintori, just off Via de’Benci and between the river and Santa Croce. Traditional Tuscan restaurant, known for it’s Bistecca Fiorentina (Florentine T-Bone steaks) and great regional dishes. Looks like an old place, and it is, but is just amazing and worth spending an evening (or lunch) sitting, eating and drinking before rolling home. Be warned, don't ask for your steak to be done anything above medium - the boys who own the restaurant also have their own cattle farm and they will be able to tell you the best cooking time for each cut.
Another good place for lunch or dinner is Francesco Vini, on Borgo dei Greci - the street between Piazza Santa Croce and Piazza della Signoria. They do seasonal produce, great Tuscan dishes as well as a selection of dishes from around Italy. And a great wine list!
Yellow Bar, on via del Proconsolo, near the Bargello museum, is great for a quick pizza (not Florentine, but very popular nonetheless) or pasta.
The Mercato Centrale is also a great place to wander just before lunch and pick out what you want to eat from the small stalls there. Lampredotto is
the Florentine specialty, but it's not for everyone. Have it if you really want to immerse yourself in the food culture - it's tasty, but many visitors freak out at the thought of it. Otherwise you can buy your fresh produce there before 2pm.
Gelati: In Florence two of the best places are Vivoli in via de’Bentaccordi (near the Dante House) and Perche No! in via dei Tavolini, just off the shopping street Via Calzaioli on the way to the Duomo from the main square Piazza della Signoria (with all the statues). There is a new one (well, a few years old now, but new in Florentine terms) just near the Duomo in a side street (via del Campanile) called Grom. I haven't had a gelato from there, but friends tell me it's good. Perhaps a compare and contrast test is in order!