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.

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.

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.

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.