We will only be there for three days so I want to make sure we don't screw this one up I know there is probably a little bit of everything - from hole in the wall joints to "reservations required" establishments.

Your recommendations would be much appreciated!

Thanks in advance

Tuscany is a large area. To avoid everyone wasting time recommending restaurants you won't be anywhere near, maybe you could tell us where you'll be.

I just had trouble with my computer, hope this doesn't post twice. Tuscany is a large area. To avoid everyone wasting time recommending restaurants you won't be anywhere near, tell us where you will be.

Since the OP hasn't responded, I will. We will be in Castellina in Chianti in June. We will probably be exploring Greve and San Gimignano among others.

flem16,

Last fall my wife and I spent a week of our trip in Italy at an agritourismo outside of Greve in the Chianti region. We had many excellent lunches and dinners from the hole-in-the-wall to reservations only in our day trips exploring Chianti. Two small, intimate and out of the way places stood out for us for their excellent food, wine and ambiance: Osteria Le Panzanelle (0577 733511) in the very small village of Lucarelli, just west of Radda. If the weather is nice try and get a table outside by the stream. The other, La Castellana (0515 2250485), is located in a very cool and unspoiled hill town of Montefioralle about a 1k west in the hills above Greve. Reservations recommended for both.

We will be near Gaiole in Chianti. We'll be making trips over to San Gimignano and up to Florence so we'll be moving throughout the region. I'm thinking along the lines of something that is not in a big city...more of the countryside experience.

I have two places to recommend in San Gimignano:

Ristorante il Dorando, which is a Slow Food member on a quiet back street off the north end of Piazza della Cisterna (vicolo dell’Oro, 2). This is Italian food more on the creative side; for example, pici with a mint pesto. Everything we had was delicious, and the creative spin kept us guessing.

If you'd like a restaurant with a view, we've eaten at Il Pozzo several times; the view is great, as is the food.

Both of those are on the fancy, formal side, though we wandered into Ristorante il Dorando for lunch, my husband in shorts, and nobody batted an eye (and at least one person there was in jeans).

Our fanciest dinner was at La Chiusa, with one Michelin star, in tiny Montefollonico. The restaurant is beautiful, the service was impeccable and welcoming. The food was also delicious (I especially remember the fig tart dessert), though the amuse bouche (a sort of one-bite greasy pizza) was horrid. Lots of local foods in season.

One factor to consider, if you haven't already, is whether you're planning to have dinner around Tuscany (rather than in the town where your lodging is). That means someone in your group will be driving after dinner, probably in the dark, on narrow, windy (though gorgeous in the daytime) roads. If you have any wine with dinner, a designated driver is a must. We try to stay where we eat, to avoid this problem.