Although it calls itself an osteria (tavern), this place much more resembles a wine bar, with a bill of fare that includes several different types of pâtés and a short list of seasonal soups and salads. The sampler of goat cheeses, which can be paired with local wines, should not be missed. Operatic arias tend to play softly in the background, and service is courteous.

22/08/2025: We didn't even have time to eat because as soon as we entered the waiter didn't accept that we had decided to sit upstairs instead of downstairs. By the time we ordered water, we were asked what we wanted to order. After asking for another minute, the waiter snorted, and at that second sign of rudeness, we got up to go downstairs to pay for the water, which he said hadn't even been brought to us because he knew that a couple of tourists, very normal young people like so many others, would leave, and so it was.

Right next to Piazza della Cisterna, this is the place to go to treat you to a traditional and high quality lunch or dinner. They don’t serve pasta or pizza, but you’ll soon forget you carb addiction as they have the most exquisite soups, with porcini, onions, vegetables… if you can’t decide, you can have two or even three small tastings. They have also cheese boards, terrines, roast meat and a good selection of home-made desserts.

Where to eat: On our visit to San Gimignano we stopped to eat at Osteria del Carcere (Prison). This is a slow food osteria which serves a number of products from one of Italy’s most famous butchers Dario Cecchini. If you do not have time to visit this butcher and his restaurants in Panzano in Chianti, then this is a good chance to try his excellent produce.

You won’t find pasta or pizza here, but you will find an array of flavourful, rustic, seasonal Tuscan soups like zuppa di porcini e fagioli (porcini mushrooms and beans), zuppa di cipolle (onion soup) and minestra frantoiana (a vegetable soup). It’ll be hard to choose just one, so you can also order 2 or 3 soups in small portions.

Some wine bars: Un Mondo di Sapori, La Cantina del Convento, Enoteca DiVinorum, Vinoteque. Make sure not to skip the renown and awarded Gelateria Dondoli!. At the Reception of Hotel Certaldo is possible to have any information you desire and book any restaurant you prefer.

The MICHELIN inspectors' point of view, information on prices, types of cuisine and opening hours on the MICHELIN Guide's official website . A hotbed of culture, Chicago caters to a wide range of culinary tastes.

Montegemoli, Via del Borgo, 39 (nordwestlich von Pomerance, bzw. von Volterra in Richtung Cecina hinter Saline di Volterra links abbiegen), Tel.: 0039 0347 5727808

Experience authentic Tuscan cuisine at Osteria del Carcere in San Gimignano - where tradition meets flavor in a charming setting.