1LA PINETA I wish there were more coastal restaurants like La Pineta. Tucked into a seafront shack on the Mediterranean, an ex-fisherman turned cult chef Luciano Zazzeri has transformed his small restaurant into a culinary pilgrimage destination with a selection of fish that brings new meaning to the term boat-to-table (he uses seafood caught from his family’s vessels). Reservations are hard to come by, especially for the handful of tables on the outdoor terrace, so book in advance (27 Via dei Cavalleggeri Nord, Marina di Bibbona; 39-0586-600-016).

2LA PORTA This tiny trattoria, tucked inside the medieval walls of the impossibly perfect borgo of Monticchiello, serves up simple, classic dishes like fresh taglioni with black truffles. The owner, Daria Cappelli, is a much-beloved local character and a total pro at working the room. Let her choose your wine; she has a great list from nearby Montalcino and all over Tuscany (1 Via del Piano, Monticchiello; 39-0578-755-163).

3TRE CRISTI Tuscany may be famous for its steak and pasta dishes, but its excellence as a fish destination is much less well known. Siena’s Tre Cristi showcases the scope of the region’s offerings—with dishes like calamari and squid with a timbale of eggplant, and a fabulous seafood risotto with zucchini flowers. If you can splurge, go for the tasting menu (1/7 Vicolo di Provenzano, Siena; 39-0577-280-608).

4ARNOLFO For a destination meal that is more blowout than mom-and-pop, book a table at this two-Michelin-starred temple outside of Colle di Val d’Elsa. Purists might be startled at some of the pairings—suckling pig with cranberries or foie gras with cherries—but star chef Gaetano Trovato quickly wins them over. It’s a long night of eating, so it’s best to leave the little ones at the hotel (Via 20 Settembre, 50–52 Colle Val d’ Elsa; 39-0577-920-549).

5CIBRÈO Consider Fabio Picchi the emperor of the Florentine food scene, with all the trappings of such a position—multiple culinary palaces and a reputation that provokes awe and, sometimes, envy. Picchi is the man who has married traditional ingredients with a more modern ethos: There is no pasta or grilled meat here. Instead, signature dishes include roast duck stuffed with minced beef, raisins, and pine nuts, and sausages with succulent beans (8/R Via del Verrocchio, Florence; 39-055-234-1100).