Virtually the only thing I dislike about Tuscany is going there with a return ticket. There are few more-agreeable ways to spend time than strolling through the great cities of Lucca, Pisa, Siena and Florence. But for me, the supreme pleasure is puttering along country roads through one of the most distinctive and civilized landscapes in the world. A patchwork of wine and olive estates dominates the Chianti district, a romantic 40-mile swath between Florence and Siena. Memorable sites include the picture-book wine villages of Castellina, Radda and Volpaia, plus the 13th-century fortress hamlet of Vertine; the ancient abbey-wine estate of Badia a Coltibuono (eight miles east of Radda); and majestic Castello di Brolio (13 miles southeast of Radda, near San Regolo). Outside the Chianti Classico area lies Monteriggioni (described in Dante’s “Inferno”) and the picturesque medieval city of San Gimignano. The Val d’Orcia wine region of southern Tuscany begins 45 minutes southeast of Siena, its vineyards producing celebrated reds such as the full-bodied Brunello di Montalcino and the refined Vino Nobile di Montepulciano.
Generally, we choose fall for our Tuscan rambles — when the summer crowds have gone home — but I also enjoy traveling in late spring, when mornings see the mist dissolve to reveal groves of silvery olives stirred by a gentle breeze and pale-green vineyards with newly unfolded leaves.
Private Market Tour
For a taste of Tuscany, I recommend Divina Cucina’s one-day market tours in Florence, offered Monday through Friday. The company can also arrange customized day trips, and it offers weeklong culinary classes in Chianti. Book well ahead.
One of the great gastronomic pleasures of a visit to Tuscany is its superb charcuterie, known in Italian as salumi. Almost every town in Tuscany boasts a salumeria (shop selling ham and sausage) that proudly vaunts its own recipes and the quality of its products. Perhaps the most famous salumeria in Tuscany is the Antica Macelleria Falorni on Piazza G. Matteotti in Greve in Chianti. The shop has been in business since 1729, and is currently run by the eighth generation of the same family.
Italy's Best Pecorino
Made from sheep’s milk, pecorino di Pienza — named for the town 35 miles southeast of Siena — is widely considered to be the best in Italy. We visited an artisanal producer, Fattoria Pianporcino, for a tour and a tasting. Its pecorino is softer and creamier than the familiar pecorino Romano. The cheese can be aged in different ways: combined with pepper, washed with tomato paste or wrapped in walnut leaves. Reserve your tasting in advance.
Medieval Wine Town
Perched on a hill, with prominent fortifications and winding streets, Montalcino is the embodiment of a medieval town and the home of one of Tuscany’s most celebrated wines, Brunello di Montalcino. The largest selection from local producers is to be found within the town’s 14th-century fortress, at Enoteca la Fortezza di Montalcino. The staff are knowledgeable, and the shipping back home is reasonable.
At Castello Monterinaldi in Radda in Chianti, 26 miles south of Florence, winemaker and proprietor Daniele Ciampi took us on an extensive tour of the cellars, then led us through a comprehensive tasting. Monterinaldi offers a full range of programs for visitors, including a tour and tasting with lunch, a “Winemaker for a Day” experience, a cooking class including a variety of traditional recipes, and a hiking tour of the estate followed by lunch.