On the coast of Long Island, in Southold, N.Y., the freestanding building that houses Caci North Fork resembles a modest home. It’s a fitting aesthetic for the family-owned restaurant, which serves Italian cuisine in a cozy dining room of just 28 seats. Umbria-born chef Marco Pellegrini incorporates modern and traditional touches into his seasonal dishes, which currently include black summer truffle atop buffalo milk ricotta ravioli and taglierini alla carbonara with house-cured pancetta. Pellegrini also serves as wine director for Caci North Fork’s Award of Excellence–winning program, which spotlights the nearby budding wine region—including producers such as Macari, Shinn Estate, Anthony Nappa and Clovis Point—in addition to Italian classics like Gaja, Antinori and Tenuta San Guido. Nearly every bottle on the 115-selection list is also available by the glass, and many are priced at less than $100.