Tuscany itinerary: Six days of wining and dining

Spend your first few days getting to know Tuscany’s legendary Chianti Classico red and its siblings in the sun-kissed valleys and craggy hills of the Chianti region between Florence and Siena.

You can do much of this vineyard visiting and sightseeing in three days’ time.

The absolute don’t-miss vineyards for buying include Villa Vignamaggio, Castello da Verrazzano, Castello di Ama, Castello di Volpaia, and the granddaddy of them all: Castello di Brolio, where modern Chianti was invented.

Don't forget to pay attention to the "Before you Leave Home " box at the end of the itinerary covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries work.If you didn’t have a chance to plan or phone ahead to arrange degustazione (tastings), Castello da Verrazzano and the Rinaldi Palmira shop for Castello di Ama all welcome degustazione drop-ins.

I recommend basing yourself for the first night or two in a mini-apartment at Villa Vignamaggio, a gorgeous Renaissance villa where the real Mona Lisa was raised and where Kenneth Branagh filmed Much Ado About Nothing. It is near Greve in Chianti, the “capital” of the region and home to the most wine shops (there’s another good shop at the bend in the main road as it passes through Castellina in Chianti; good snacks, too).

There are also some fine meals to be had in the Chianti. None is overly fancy, but La Cantinetta in Spedaluzzo serves some of the best-prepared versions of local specialties, and is good for lunch or dinner.

You can also get a sophisticated meal at the osteria at Castello di Fonterutoli, with each course paired with one of this ancient estate's excellent wines.

La Cantinetta di Rignana is the Chianti’s lunch spot par excellence, with good, simple food and a killer vista, tucked way out in the wonderful middle of nowhere (excellent agriturismo, too).

For at least one night—perhaps two—stay in the southern Chianti at Podere Terreno, a homey little country house turned agriturismo that serves some of the most fabulous dinners you'll have in Italy—all done family-style with all the guests seated around a big table along with the proprietors.

 

It’s time to up the stakes from the fun-loving but lightweight Chianti and get into some serious Italian wine and food. South of Tuscany lies Montalcino, home to one of Italy’s most powerful and respected red wines, Brunello di Montalcino.

In the morning, stop by the local wine consortium’s office to pick up their vineyard map, then ensconce yourself in the Enoteca La Fortezza, a wine cellar installed in the bastions of the town’s medieval fortress and manned by a very knowledgeable staff.

Here you can cozy up to glasses of some of the best Brunellos, try out the less heavy-duty Rosso di Montalcino red and Moscadello dessert wine, and make a list of which labels produce the elixirs you want to bring home with you and tuck it away for later.

Brunello goes perfect with a rare bistecca Fiorentina or Tuscan game dishes, and there’s no better place to test it out than at the fine restaurant on the estate of one of Brunello’s premiere labels: Poggio Antico.

Now you could return to town to pick up your favorite Brunellos at the Entoeca, but purchasing direct from the vineyard itself is so much more fun. So armed with your map and your list, set off in search of the perfect Brunello among the vine-crossed hills of Montalcino. After a light dinner, sleep off all that wine by spending the night in Montalcino.

 

Montepulciano is a hilltown of Renaissance palazzi and Tuscany’s #2 red, Vino Nobile di Montepulciano. Its a more versatile wine than its neighbor Brunello, lighter weight and fruitier, and good with just about any food.

You can try its at any of the dozens of cantine scattered about town—many of them storefronts above vast networks of Etruscan tunnels where the wine is stored— and even have lunch farm hand-style at one of the estates, Fattoria Pulcino. But for the best “noble wines,” drop by the estates northeast of the city.

Poliziano (tel. +39-0578-738-171, www.carlettipoliziano.com), near Gracchiano, has some powerful wines, but perhaps the best Vino Nobile is produced at the La Cappezzini vineyards of the Avignonesi outfit (tel. +39-0578-724-304, www.avignonesi.it), across the Chiana canal near the village of Valiano. Their special reds are to set aside for aging, and be sure to pick up some of their pricey, velvety Vin Santo.

Return to Montepulciano for a celebratory dinner at the Trattoria Diva & Matteo and turn in for the night—your tour of Tuscan reds is over. Spend the night in Montepulciano.

 

Now that the cellar back home will be well-stocked with Tuscan reds, it’s time to cross the Umbrian border and revel in one of the few Italian white wines worth troubling over, the dry, straw-colored Orvieto Classico.

Orvieto is a stony city, rising implacably on its mesa of tufa. Spend the morning with its major sight, the jewel box of a Duomo with horribly fascinating carvings on the facade and ground-breaking frescoes inside.

Orvieto has been producing its famous white wine probably since Etruscan times, and has made an industry out of getting everyone from the Celtic French to the Roman emperors to the invading Goths and Renaissance popes more than tipsy on the stuff.

There are a couple of good cellars to help you get intimate with the semi-dry and sweet varieties of the Orvieto Classico that are seldom exported, but the best way to warm up to an afternoon in Orvieto is to let yourself imbibe a bit at the lunch table, and there’s no better place for that than at the Trattoria Tipica dell’Etrusca.

After lunch, you can hit a few of the outlying vineyards for direct sales—the best are recommended in the Orvieto chapter—or relax in town and do your shopping, and perhaps a bit more tasting, at the enoteche.

Spend the night in Orvieto.