While visiting the Chianti region, stop for lunch and wine tasting at the elegantly preserved Badia a Coltibuono. Housed in an 11th-century monastery, this organic agrotourism destination is rumored to be the birthplace of high Chianti. Reserve ahead for a table outside on the vine-wreathed terrace, and order the tasting menu, which offers handmade pasta with four pairings. Ask for a glass of the award-winning Vin Santo and take it with you as you stroll through the impressive gardens.

An organic farm outside of Pienza, Il Casale sells local produce and prepares regional Tuscan cuisine. Adults will enjoy the stunning views of the lush countryside while children are entertained by the farm animals.

Nestled amid some of southern Tuscany’s most valuable Brunello-making vineyards, this small trattoria lays claim to a most impressive wine list, one that features both heavyweight vintages you'll see exported around the world and small secret labels you're unlikely to have seen elsewhere. Local wine producers flock here for that very reason. But the wine is only half the story; they also come for a menu that features such classic Tuscan fare as pappa al pomodoro (a thick bread-and-tomato soup), and bistecca alla fiorentina (the region’s famous t-bone), as well as more unexpected choices, including a perfectly crisp fried chicken that's worth the trip alone. The restaurant owns a small wine shop next door so you can take a bottle of your favorite new discovery to go. Closed Wednesdays.

La Lodola is an example of the type of well-priced inn, with a wonderful restaurant attached, that one wishes one saw more of in Italy. It’s located close to Cortona, made famous as the setting for Under the Tuscan Sun. This tucked-away gem has a great outside terrace in the summer months and an interior that gives off an almost French bistro feeling. Chef Carlo Porcu is also the owner’s son, and the familial love he puts into his Tuscan comfort food has garnered both locals and visitors as fans. Porcu focuses on fresh pasta and regional meat dishes, and his menu changes daily based on seasonal produce and his latest inspiration.

A deli counter inside the gourmet food market Consorzio Agrario di Siena, Manchetti offers delicious, to-go thin crust pizzas, which have a devoted local following.

This charming restaurant with exposed wooden beams and simple table settings serves classic Tuscan cuisine with sweeping views of the countryside. The downstairs enoteca stores the region’s signature Brunello wines, which can be ordered in the restaurant by the glass, bottle or flight.

The epitome of a classic trattoria, Da Fiorella in Pienza is a good choice for lunch or dinner, where mountains of pasta and regional specialties are served up by a friendly wait staff.

Family-run Latte di Luna is a favorite for locals and visitors alike thanks to its hearty Tuscan menu. Request a spot on the leafy outdoor terrace, which is popular in the summer months, and enjoy regional specialties like maialino—roasted suckling pig—or pasta with truffles and wild boar. Everything is freshly prepared with an emphasis on local ingredients, and the wine list features bottles from nearby vineyards.