For an epic, blow-out, once-in-a-lifetime gourmet feast, look no further than this two-Michelin-starred destination restaurant close to Siena. Chef Gaetano Trovato is an understated genius and his creativity comes out in his inventive touches—foie gras arrive with stewed seasonal cherries; tortelli with succulent strips of rabbit, herbs, and licorice; Chianina (the Tuscan breed of long-legged white cows) veal tartar with chanterelle mushrooms; and a delicious suckling pig with tangy green apples. The plates look straight out of a gourmet magazine photo shoot, the wine list forms an education in Italian vintages, and everything tastes exquisitely delicious. All of which is to say that a meal here is worth the high price tag.

Relaxed, but refined restaurant in Tuscany in the hamlet of Montalcino.

Most people who come to Southern Tuscany expect to eat plates of steak and pasta so this high-end, fish-centric spot provides a welcome surprise. Started by three foodie friends on a quiet street away from Siena’s tourist fray, the inventive and romantic spot has a wonderful tasting menu, as well as dishes like calamari eggplant parmesan, with crispy strips of delicate squid battered with cheese on juicy pieces of eggplant. Sommelier Alessandro Baccheschi is a gem: let him take care of the pairings, and don’t miss a tour of the original cellar housed in the vaulted basement. Closed Sundays.

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.

The Michelin-starred restaurant of Relais & Chateaux Il Falconiere is located a 15-minute drive outside the town of Cortona. The kitchen offers painstakingly prepared dishes, including magnificent bread. Seated either in the limonaia or on the terrace, you can complement your meal with wines from the owner's own vineyard, which lies right below the restaurant. Try the Ardito, a nice blend of Syrah and Cabernet. Il Falconiere also hosts an excellent cooking school, with courses lasting from an afternoon to a week.

Halfway between Cortona and Siena, in the center of quaint Lucignano, Il Goccino creates sophisticated takes on classic Tuscan dishes. Sit outside on the terrace and enjoy beautifully prepared pasta and meat dishes and regional wine while admiring the views of Val di Chiano.

We know people who have flown all the way from Brazil just to eat at this tiny restaurant in Pienza—it has a core of devoted gourmet followers—for one of the best culinary experiences in Tuscany. Among the standouts are the melanzane alla mozzarella, pici (the area’s thick hand-rolled version of spaghetti) with duck ragu, and a succulent cinta senese (the region’s special pork) crusted with almonds. The owners are straight out of central casting: the husband a jovial and opinionated former banker, and his somewhat temperamental wife who cooks with the attention of a surgeon, albeit one with a glass of wine in hand. Their regional wine list has the mark of being created by someone who appreciates a good vintage themselves. Closed Thursdays.

Considered one of the town’s—and region’s—best dining experiences, La Grotta is housed in a 16^th-century building with an elegant garden. The restaurant offers an exciting gourmet menu that blends traditional Tuscan flavors with a contemporary flair.

Housed in a sweet clapboard structure right on the beach, this restaurant features a perfect mix of low-key charm, impeccable service and incredible fresh seafood—not to mention an encyclopedic wine list. The crudo, Italy’s answer to sushi, melts in your mouth, while seafood straight from the owner’s two fishing boats comes stewed in a perfect blend of olives, capers, and sun-ripened tomatoes. Wine from the region, including an excellent and well-priced bottle of vermentino from Grattamacco, nods to the fact that you are only 15 minutes from Bolgheri, the home of superstar vintages like Ornellaia and Sassacaia. Closed Mondays and Tuesday for lunch.

Inside a ridiculously picturesque walled village close to the Renaissance town of Pienza, La Porta has become a must-stop for both visiting foodies and well-heeled locals. They come for one of the region’s best tagliolini al tartufo (a perfectly creamy truffle pasta) and for the multilingual owner Daria, whose selection of local Brunello, from Montalcino, and Vino Nobile from Montepulciano, is priced at a fraction of what you would pay back home. Book ahead to snag a table on the terrace overlooking the UNESCO-protected Val d’Orcia.

La Taverna, housed inside the fairytale Castello di Banfi, serves imaginative yet authentic Tuscan cuisine. Multiple-course tasting menus, which may feature specialties such as beef carpaccio and pinci pasta with chanterelles, are complemented by the estate’s fine wines and served in the cozy restaurant under brick-arched ceilings.

In the historic town of San Giustino Valdarno, located on the luxurious Il Borro estate, Osteria del Borro is a delightful restaurant that serves modern interpretations of Tuscan classics. With warm lighting, natural wood furnishings and a splendid view of the medieval estate (which has been wonderfully restored by the Ferragamo family), the osteria is a cozy spot.

Osteria del Teatro lives up to its theatrical name both for its beautifully crafted meals and its dining rooms filled with whimsical collectibles. Tucked in a quiet alley off the main square, the restaurant serves inventive, regional cuisine that focuses on fresh ingredients and changes seasonally.

Le Logge may not be a secret anymore, but there are few nicer places to eat in Siena, especially within a stone's throw of the unmissable 13th-century Campo. Housed in a former pharmacy near that masterpiece of a piazza, the restaurant has two levels of seating: the best tables are in the ground-floor dining room, with its old cabinets lined with wine bottles. (Don’t let them seat you on the less atmospheric second floor). The big open kitchen turns out largely traditional Tuscan dishes that put an emphasis on seasonal ingredients, many of them so local they come from right outside the city's medieval walls. Among the highlights: autumn's pumpkin-filled ravioli and the malfatti all’ Osteria, yummy ricotta-and-spinach balls that are a year-round signature. Closed Sundays.

The premier restaurant on the Castello Banfi estate, Sala dei Grappoli features sophisticated Tuscan cuisine in an elegant country setting. The various tasting menus reveal the rich flavors of the region and are expertly paired with the wines from the Banfi vineyard. Sit inside the candlelit dining room under exposed wood beams or alfresco, with views of the castle and countryside.