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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.

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Our Favorite Florentine Steak

The Officina della Bistecca (Via XX Luglio 11. Tel. (39) 055-852-020) in Panzano in Chianti is my favorite spot for bistecca alla Fiorentina, a rib steak of Tuscany’s famous Chianina beef prepared with flair by ebullient star butcher Dario Cecchini. The fixed menu begins with beef tartare and continues with several cuts of steak, seasonal vegetables, Tuscan beans with olive oil, roasted potatoes with onions, and olive-oil cake. You can bring your own wine or try the included “Italian military spirits.” Devoted carnivores might also enjoy taking the “Butcher for a Day” class.

A Private Tour of the Markets

For a taste of Tuscany, I recommend Divina Cucina’s one-day private market tours in Florence, offered Monday through Friday (book well in advance).

One of Italy's Best Pecorino Cheeses

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.

The Castello Monterinaldi Winery

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, an intensive cooking class and a hiking tour of the estate followed by lunch.