Help with 3 day trips with car from home base near Florence


I am hoping for a little help with our trip plan please.

My mother and I are having a hard time deciding on day trips from our B&B in Prato since we have to return every day. (25 min drive from Florence but we will have a rental car for the whole time.)

We have already booked our B&B and arrive at 4:30 pm on Monday, September 21, 2015 and leave the morning of Friday, September 25, 2015. Then we are spending one day/one night in Florence (as my mom has been here already so that's all we wanted/needed) then we are off to the Amalfi Coast by train September 26, 2015.

So that leaves us with 3 whole days to explore Tuscany:

We are very interested in having one day to take a scenic drive to the chianti region and visiting wineries and having lunch and/or dinner with a view. Perhaps stopping in the little towns? Castellina? Greve? seem popular.

Would this take a whole day? or can/should we see other places as well? or save for another day trip?

ex. San Gimignano, Siena.

Fiesole and Pistoia are close to us and look nice. Are they worth visiting?

We like the Southern part of Tuscany (probably should have booked our B&B closer haha) but may be too long of a day to do from where we are staying?

Will probably skip Pisa and Lucca area.

As you can see I am confused. Open to suggestions.

Thanks again for your help.


Well-known member
Ideas for day trips


Your day trip into Chianti is probably good for a full day if you take it easy and just enjoy a leisurely pace. You might enjoy adding Radda in Chianti and Montefioralle to you list of little towns to visit.

Fiesole is a beautiful historical monument - though I wouldn't say it would take all day. You can definitely combine it with the afternoon you move to stay in Florence. Maybe take the morning to visit Prato - which is actually quite interesting and then in the afternoon visit Fiesole before checking into your Florence hotel.

Though it is a drive, you can definitely take a day to visit Southern Tuscany, I would sandwich it between the day in Chianti and the day you change hotels - so that you have to less stressful days before and after.

If you haven't been to either Siena or S. Gimignano - then keep them on your list. I suggest doing Siena first and then enjoy the countryside coming home and maybe a drink in the square at San Gimignano...very picturesque.

Buon Viaggio
Donna Denise
Buongiorno Donna,

Thank you for the quick reply and the information. It has really helped.

So we have decided to do one day trip in Chianti as you suggested. Perhaps starting in Greve, with a quick diversion to Montefioralle and Badia Passignano. Then onto Panzano and/or Radda and/or Gaiole (is there time for all or pass on some of these?) then to Castellina.

From there thinking of on the way back stopping at Colle Val d'Elsa and/or Barberino Val d'Elsa.

is this too much?

Day 2 or 3

-Siena, Monteriggioni and San Gimignano then home

-Have not decided on the other day yet. I am not sure my mom will want to do the long drive to the southern part.

When we check out of our B&B in the morning we have to have the rental car back in Florence by 2 pm. Do you think it makes sense to see Prato in the morning and then Fiesole and then to Florence to drop off the car? or after Prato drop off first and take the bus to Fiesole? or skip?

We could also go to Prato the day we arrive for a quick tour and have dinner since it is close to our B&B?

Sorry for all the questions. I appreciate you opinion and help.

Thank you,


The Tuscan Expert ;-)
Staff member
I like Donna's proposals and the changes you've made. I would suggest on day 1:
Greve, Montefioralle, Badia a Passignano
on to Panzano, then Radda then back to Castellina - skip Gaiole.
On the way back, do the drive from Castellina to Monteriggioni just for the beautiful views of the countryside (which you wouldn't do the other day between Siena and Monteriggioni), then maybe dinner at Colle Val d'Elsa OR Certaldo.

Day 2 - as you've planned. I'd do dinner in San Gimignano.

Day 3 - The drive to southern Tuscany, if you take the A1, is around 1.5 hours. If you do it, I would suggest driving to Montepulciano, seeing that, and from there continuing on to Pienza and then to San Quirico d'Orcia, then on to Montalcino.
If not, another possibility would be Arezzo+Cortona - the drive from Prato is less than an hour. Arezzo is visited but it is off most people's itineraries so it is never crowded and retains its more authentic feeling of being just locals. I highly recommend it. Cortona is a small hilltop village and is much more popular given its role in the movie "Under the Tuscan Sun" -- it is quaint and charming, but not a requirement. You could spend the entire day in Arezzo ;)

If you have time when you first arrive, I'd recommend that time in Prato.
Fiesole you can do it once you're in Florence - catch bus 7 and it takes you all the way up but of course, if you have the time to spend, you can also do it the morning of day 4 before dropping off the car.
Thank you very much for the information, it really helps. Now I just need to choose a vineyard to visit for wine tasting and lunch and restaurants. :) Any recommendations?

Btw, is it hard to find our way driving home at night?