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If you want to make it special, choose Da Caino : it is Montemerano's gastronomic table, with contemporary Tuscan cuisine by Valeria Piccini and a very extensive wine list. However, expect a high bill: the tasting menu is listed at around 210 € per person. It is not the right choice if you are simply looking for a good plate of pasta or an unceremonious dinner. Book in advance and check the opening hours: the restaurant is closed on Tuesday and Wednesday.
For a simpler meal, I would rather look at the Vecchia Osteria Cacio e Vino, or at the 16, Via del Bivio. It offers Tuscan and Maremma-style cuisine in an osteria spirit, with local wines; the budget should be more reasonable, but I prefer not to quote you a specific price without an up-to-date menu. It closes on Thursday. My choice would therefore depend on your mood: Da Caino for a real occasion and a gastronomic experience, Cacio e Vino for a relaxed dinner in the village. In both cases, call before coming, especially in the low season, as days and services may change.
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