I’d like to ask for opinions on our itinerary from Florence to our next overnight stop in San Gimignano. A September, Wednesday is our travel day, starting at the car rental pickup from the airport at around 9 AM. I used ViaMichelin for suggested routes.

We want to:
- Visit 1 or 2 beautiful small towns (Radda and Volpaia look pretty, not sensing that folks adore Greve)
- Visit 2 beautiful wineries (Karen Brown’s Itinerary recommends Castello di Volpaia, Castello di Alboia, Castello di Meleto, Castello di Brolio). As you can see, we like the Castle idea for the historical and architectural setting...but finding a wonderful red wine is most important especially the Super Tuscans and Brunellos (we'll ask more about Montalcino later).
- Have lunch and relax at a lovely restaurant with a beautiful view.
- Arrive in San Gimignano – Antico Pozzo before dark
- Travel scenic routes – wanted to use S222, but ViaMichelin recommends the Autostrada to Volpaia and SR249 to San Gimignano.

We do want to poke along on our first driving day so I’m trying to focus our sightseeing around the areas Radda, Volpaia, Gaiole, Castellina (our exit toward San G.)

Thanks for any experienced advice our Tuscany veterans have to offer.
Terry

Hi there,
We loved Greve! We would definitely recommend it. It's small but very charming.

Hi Terry,

Your plan sounds good, but personally, I would rather take the slower, more scenic route and visit fewer places. The smaller roads, S222 and smaller, are very windy and take much longer than you thing they will.

We tasted and toured Castello di Brolio. This was a few years ago, but their Chianti Reserva was fabulous. You can tour the grounds and chapel of the castello, but not in the inside. The family still lives there, Antinori, I think?

Their restaurant is supposed to be very good, but advance res are definitely needed.

We had an indulgent lunch at La Badia di Coltibuono, east a bit of Castellina. Excellent! Our hotel made res for us and it was busy in May for lunch. Great views and we took a tour of the old abbey and gardens and wine cellars. This is Lorenza de Medici's home and where she has her cooking classes.

If you do want to make 4 stops on your drive on to SG, start earlier from Florence. the car rental could very well take much longer than you think too!

Buon appetito!

We spent a day driving from San Gimignano as far as Greve on the S222. It took us 4.5 hours with a picnic lunch stop in Radda. We decided to get on the N2 to return as the S222 is a very slow road with all the twists and turns. We never got out of 2nd gear the whole time. The scenery is lovely but I think it would be difficult to stop in several towns, visit two wineries and have a leisurely lunch.

I think you could visit two or three towns and could perhaps pick a winery that offers a lunch on site. There have been recommendation on this site if you search under Chianti wine tours. Here is one link that was listed with winery tour and lunch.

http://www.verrazzano.com/

Great advice! Thank you.

I especially like Dayle's experience with La Badia di Coltibuono.

Crazy4Travels link for Castello di Veranzano looks nice too. Has anyone been there?

We will be in the region for a week (San G for 2 nights, then Cortona for 4 nights). I wonder if we'll get our fill of scenery without trying to tackle S222. We do want to feel like we can stop and look around.

Here is a few good thread similar to your question.

http://www.fodors.com/forums/threadselect.jsp?fid=2

Thanks again for helping me Crazy4Travel. The link seems to be incomplete (I've done the same thing before). Would you mind giving it another try for me.

Sorry about that...it does not appear to be working. If you do a search with Chianti wineries in the search box and click Italy to the right...you will get several useful threads. There are several recommendations for wineries.

The town of Castellina is of little consequence but there are several wineries in that area and the countryside is lovely. Radda is a cute town with beautiful views. It was getting late in the day by the time we got to Greve so we decided we should find a quicker way to get back to make it home before dark.

I only caution you about the time as some of the winery tours take several hours...a couple of hours for lunch...and some time to see the towns. The S222 is a slow road...especially the stretch between Radda and Poggibonsi. It is very scenic though...If you narrow your stops down you won't be rushed for time.

It's nice to arrive to San Gimignano after the bus tours leave for the day. Make sure you take a walk around the walls of the town...it's lovely in the morning. There's a path to follow and the views are jaw dropping. There's a great restaurant called Chiribiri...first left as you come in the main gate. The food and serve are wonderful but you need to make a reservation (cash only). The pumpkin ravioli are out of this world!

Good luck with your planning and enjoy!!

Thanks so much, Crazy4Travel. I'm sure we'll put your advice to work. I'll make sure to include Chiribiri on our must do list.

You won't be sorry about Chiribiri...it is a family run Trattoria with excellent food and prices. Three course meal for two with wine was 45.00 Euros!

ttt

One more note about Chiribiri: be sure to book as it is tiny. Well worth it; my favorite in the area. Panna cotta with chocolate sauce was tooooo delicious.

Searching for any other opinions