For the first 5 days, we're staying in Chianti. For the last two days, in Montalcino. Here is the rough plan - but need help deciding on Friday! This is very restaurant-focused - I haven't gotten much further than that.

Monday: Explore Castellina, Greve and Radda. Dinner at Ristoro di Lamole.

Tuesday: Florence. Uffizi in the morning, lunch at Mario’s or Nerbonne. Duomo, etc. in the afternoon. Dinner at Cibreo Trattoria.

Wednesday. Siena all day. Dinner at Castelvecchio.

Thursday: More Florence - Academia, mercato, etc. Back to Castellina for dinner at Il Pestello or Osteria Fonterutoli (any preference?)

Friday: Volterra. Then San Gimignano late aft. and dinner at Chiribiri. OR more in Chianti towns, wineries, etc, since we haven't had much time there??

Saturday: Drive to Montalcino, explore that. Go to Pienza. Dinner at Latte di Luna.

Sunday Drive around, go to Sant’Antimo Abbey, lunch at I Poggioli in Buonconvento, dinner at Grappolo Blu. (Is this too much?)

Thanks for any advice!

I'm not an expert in restaurants in Italy, but I have been there, and honestly- why bother pinpointing and microplanning your dinners, etc? I at first felt the need to do the same, but at the end, had dinner where my legs carried me. They tasted great all the same! You can't go wrong in Italy!

I know, it probably seems obsessive, but that's just me! But on the other hand, there are just restaurants I've heard so much about that I can't imagine not trying them.

Sounds like my kind of trip! I wish I could be of more help to you on the Tuscan towns. Have you looked at the SlowFood Italy site?

Make sure you get to Cibreo early unless you don't mind a bit of a wait. Please continue to check in and let us know your plans as you know them so we can salivate! I might consider Sostanza for my lunch on the second day in Florence..it is not too far from your path..

While I can't speak to restaurants in Chianti, I highly recommend Latte di Luna and Grappolo Blu in southern Tuscany. We love San Gimignano and hope you do, too! Hope this helps...

Another vote for Latte di Luna! The pasta with truffles is a dish that remains embedded in my sensory memory.

Oh, you have some good choices!

I would suggest da Sergio instead of Mario or Nerbone for lunch in Florence. It is a true foodie find, and just behind the market stalls in the San Lorenzo market area. If you can't find an address, I'll try to. OR east lunch at da Sergio on Thursday. You will be glad. Inexpensive, everything incredibly freshly prepared, a total local place. Incredible and my favorite. I think there is fish on Thursday and Friday but always other choices too. The seafood fritto misto is about the best I have ever had.

Chiribiri is well worth a visit to San Gimignano. I think you should definetly go there. Chiribiri and the Duomo interior are why I like SG. If you're going to SG, do both. Both are worth the trip, and there is that Gelataria Piazza that is killer, too. But you'll also need dessert at Chiribiri.

You are going to love Latte di Luna. I am glad you are planning ahead, because I'm an obsessive restaurant planner, too, and have actually been out of luck once for lunch at Latte di Luna. Call, reserve, whatever!

I wait all year to eat in carefully picked restaurants, and I know that we all have our own styles, but I do like an obsessive eater. ;-)

Hi Chelsea,

My one comment is that I don't think you need or will have time to explore all 3 Chianti towns on day 1. Spend more of this day wine tasting!

We loved lunch at La Badia di Coltibuono east of Castellina. Reservations needed.

Also, I don't know how big an eater you are, but I can't do more than 1 big meal a day (as much as I'd love to in Italia). I think you will end up having some small lunches/dinners!

Buon appetito!

Another high recommendation for Latte di Luna. As someone has already stated make sure you make a reservation especially if you want outdoor sitting.
We ate there last May and they had one 7:30 sitting and then placed the fully booked sign up.

Yes, be sure to reserve at Latte di Luna. We were there last January (!!), called about noon, and were lucky to get the last two seats at lunch on a Monday!

Just another vote for Latte di Luna. I an american living in Pienza the last few years. During the summer you MUST book at least a couple days before because they do book up fast! Unless you are vegetarian be sure to order the Maialino!

Driving into and out of Florence is a bit of a hassle. Is there any way that instead of breaking up your Florence visit, you could stay over in a basic room in the centre. It definitely takes at least 2 full days to absorb and explore this magnificent city so don't take away one of your days. Staying overnight and strolling through the piazzas in the evening would be my recommendation. Otherwise I think your itinerary looks great! Tuscany is sublime...

I'm going to be in Tuscany in April and am wondering, since there are so many recs to eat at Latte di Luna in Pienza...are they open for lunch too and if so, are lunch reservations necessary as well? Thanks.

Yes, Latte di Luna is open for lunch, but they are closed on tuesdays and I would always book in advance. It's a very simple place, but it is always popular.