Help me plan my Tuscany driving tours
 

Hello. My wife and I will be in Italy in late April. We are going to base in Florence. We will get to Florence on a Saturday and leave on the following Thursday.

I realize there are better places to base for seeing Tuscany, but I can get free lodging in Florence so that is where we will base.

I am trying to figure out what towns to see and on what days. I'm thinking we will rent a car for three days or so and try to group the towns logically to let us see multiples in one day. The towns we are looking to go to are:

1. Pisa
2. Lucca
3. Fiesole
4. San Gimignano
5. Volterra
6. Cortona
7. Siena
8. Montalcino
9. Pienza
10. Montepulciano
11. Orvieto
12. Assissi

So given the above

A. What would you suggest be my groupings for each day?

B. Are there any that are best done by train instead of car?

C. Did I include any towns that are yawners?

D. Did I omit any towns that are no brainer must do's?

E. Are any of these just too far away from Florence to be included?

understanding that florence is free....so you are starting from there......and i am assuming that you are not with kids, so you will have more stamina than kids do.....in terms of site seeing......
pisa is far and not so great.....i might skip it this time if i were you
you can do lucca and volterra dand san gimi in one day if you are super ambitious
and siena and montepulciano and siena in one day
orvieto will be a day trip in its own
as would assissi
thats a start anyway

You'll be happy to know that Fiesole, on your driving list, is actually just up above Florence and would make a great dinner/end of day place- maybe even for your last night. You can take the bus up (up, up, up)- it took, I think, about 20 minutes from near the Duomo where we stayed. It felt like a separate little village, to walk around, with all the city spread out below! I wanted to see Volterra for the marble/geology and a highlight was a real workshop where the artisan gave me some different chips, showed us around, etc.(It will be in your guidebooks- I can't remember.) There were a whole lot of tacky marble tourist shops and not much else on the main street! I believe that would be the reason to go? Orvieto, as already posted, is a full day car trip but not to be missed- besides the cathedral the town itself is wonderful. Of course, if you are wine lovers, then you'd have to pick # 8 and #10 (both gorgeous)! San Gimignano was a long drive, and spectacular, but getting lost on the way back was beautiful- remember, just the driving itself is so beautiful- the views as you make your way to whatever destination(s) you ultimately choose. We also really enjoyed Siena, but you could do that easily by bus and avoid a driving day. If you are flying into Pisa (?), we were there just long enough to go to the Leaning Tower for the obligatory photos and I don't see where you really have time, unless combined with Lucca. Wherever you choose, you will be happy!

For 3 days you have 12 towns - way too many IMO. Here are my comments...

One day should be spent seeing the Chianti countryside and villages.

One day for Siena with a stop in Monteriggioni.

One day for Volterra and San Gimignano.

Other than that, Lucca can be combined with Pisa (if you're strong on going there).

All the others (except Fiesole) are too far for daytrips IMO.

Thanks for all the great information folks. I thought I had too many towns for three days so the comments helped confirm that.

I am thinking of dropping either Siena or Assissi. By the looks of the travel distance, Assissi would be the one to go.

Any other thoughts for me?

Personally I would drop Pisa and pretty much skip west Tuscany. If you do justice to Florence and Fiesole, then you're only going to have time to adequately visit a portion of southern Tuscany. Not counting the day you arrive and the day you depart, you're left with 3 full days and you could easily spend 3 days just taking in Florence and Fiesole. You really don't want to rush your exploration of Tuscany. Map out a drive that takes in a few of the hill towns and just follow your instincts of where to stop. I'd highly recommend strolling through Montepulciano and visiting San Biagio church just outside. Also would take the drive to Sant'Antimo and try to get there to hear the monks chant. Don't skip Siena - it's a treat.
You'll also find that a lot of time is taken up getting in and out of the city center of Florence...plan your excursions efficiently. On my family's first trip to Italy, we crammed in way too much and a lot of it was a blur. We figured "we may never get back!" But we did and we've learned to take our time and truly take in the beauties that Tuscany especially has to offer. You're going to love your trip though, no matter what your itinerary ends up being.

Definitely skip Orvieto, Cortona/Assissi this trip. I agree with Tuck - spend one driving through the Chianti countryside, visiting vineyards. Badia a Coltibuono is a beautiful place for lunch and has tasting room, but go to www.chianticlassico.com for info on other vineyards to visit. I think you could do another day (very full) Siena/Monteriggioni/San Gimingnano/Volterra. Although this may be better split into two. A third day could be the southern Tuscan towns (8-10), but it may be easier to do Lucca and Pisa, based on proximity. Really depends on your driving ambition and what you want to see more. I know the feeling of wanting to see it all, but you will have a better time with a slower pace.

I agree with the overall summary: You have great selections, but you don't have the time.
You need 2 full days in Florence. This leaves you two days for day trips.
I would probably start with day trips.
Sunday traffic out and into Florence is much easier.
Possible plan:
Day 1:Take 222 to Greve and then Castellina.
Then take 429 west to Poggibonsi. Then take SP1 to San Gim.
If you start this day early, you can do this. You MIGHT hit Volterra (dinner?)before you head back.
If you plan dinner,you may want to go to Volterra first and eat at San Gim.
Day 2: Drive to Montepulciano,Pienza,montalcino area.
Day 3:Florence
Day 4: Train to Lucca in the am and eat lunch there. After lunch,return to Florence.
You could reverse the order,but be sure and keep your overall plan "open".
You may enjoy Chianti so much that you find that day #2 will need to be San Gim/Volterra.