11 Best Sights in Tuscany, Italy

This Romanesque abbey has been owned by internationally acclaimed cookbook author Lorenza de' Medici's family for more than a century and a half (the family isn't related to the Florentine Medici). Wine has been produced here since the abbey was founded by Vallombrosan monks in the 11th century. Today, the family continues the tradition, making wines, cold-pressed olive oil, and various flavored vinegars. Don’t miss the jasmine-draped courtyard and the inner cloister with its antique well.

One of the highest Chianti Classico vineyards, at an elevation of 370 m (1,200 feet), Castellare di Castellina is known for its panoramic vistas and its renowned Super Tuscan, I Sodi de S. Niccolò. One-hour visits, by reservation only, include a tour of the historical winery plus a tasting of four to five wines; you can also opt for Tuscan cheese and cold cuts for an additional charge.

One of Chianti Classico's top estates, Castello di Ama offers 90-minute visits that include a guided tour through the estate, a look at the historical cellar, and a tasting of three wines. Along the way, you'll see site-specific contemporary art installations created by artists from around the world. If you'd like to linger, stay the night in one of five suites in the 18th-century manor house, Villa Ricucci.

Seven different wine tours are on offer here, including a few that involve some very good food. In the capable hands of the Mazzei family since the 11th century, this gorgeous estate is a perfect place to taste some very fine wines, which pair well with items on the Tuscan menu in the osteria.

It's a pretty drive up winding roads to this 13th-century fortress. Attached is an 18th-century villa; a wineshop serves tastes of the locally produced wine as well as honeys and jams. It's worth visiting the castle, which is possible by guided-tour only (reservations required), to get a sense of how 18th-century aristocrats lived; the tour also includes a visit to the cellar and the gardens. If that doesn't interest you, proceed directly to the enoteca for a tasting. Apartments clustered near the castle are available for rent.

Tours here take you down to the cellars and through the Renaissance gardens, and end with a wine tasting. You can also have a delicious crostino on a terrace with latticed grape leaves forming a beautiful bower above; the view from the terrace stretches for miles. Lunch and dinner are also available, and all the food pairs beautifully with their wines—which they've been making since 1170.

South of Panzano, the organic Fontodi wine estate owned by Giovanni Manetti produces famed Sangiovese wines. Tours, by appointment only, include a visit to the cellar and a tasting of several vintages. The family also owns an agriturismo, Teute di Pecille, with eight apartments in two traditional stone farmhouses.

This family-run wine estate specializes in Vernaccia di San Gimignano, Tuscany's best-known white wine, and has a history dating to the 10th century (though its current owners took it over more recently, in 1977). A one-hour visit includes a tour and tasting of four to six wines. The property also includes three apartments inside a former convent.

At this small enoteca on Piazza della Cisterna, you can sample and purchase the fine wines, olive oil, and flavored vinegars made by Castello di Volpaia. Booked in advance, tours in English of the winery and olive press are also available.

The cellars of this venerable winery date from the 17th century and hold almost 200 oak wine barrels. Some of Italy's most famous wines are produced here, including an excellent range of Brunellos, a fine Rosso di Montalcino, and the estate's special Super Tuscan brands—Brusco dei Barbi and Bruscone dei Barbi. Olive oil, salami, and pecorino cheese are made at the winery's organic farm. Guided tours of the cellars are followed by wine tastings, during which you can also sample the other products.

At this family-run and -operated establishment, you can do a simple wine tasting, or taste while eating lunch or dinner at the rather fine restaurant. It's also possible to stay on the estate in restored farmhouses.