This 2-week loop includes some of the best-known of Italy's winegrowing regions, a few oenological surprises, and some major artistic sights, too, as neither man nor woman can live on wine alone.
Day 1: Florence
A good start for this tasting trip would be in Piazza Antinori, named after the vineyard barons who own the city's most refined restaurant-enoteca (wine cellar) there, the Cantinetta Antinori. For something more down-to-earth and local, hop around a couple of the excellent wine bars in the Oltrarno. Note that most of the best bottles you will find at less expensive restaurants tend to be chianti, while highbrow places have labels from farther afield.
Day 2: Carmignano
Carmignano, just outside Prato, can boast one of Tuscany's oldest winemaking traditions, and yet it is barely touched by foreign tourists. This is even more surprising considering its proximity to Florence and the potential for day trips. It produces excellent reds but is best known for its vin santo, enjoyed with the local, hard cantucci biscuits.
Days 3-4: Chianti
These vineyards need no introduction to wine enthusiasts, and many of them can be freely visited (the top places ask that you reserve around a week in advance). Only some, however, have accommodations for visitors. One of the finest places to stay is Vignamaggio, just north of Greve, a top-quality producer with excellent villas and apartments. For obvious reasons, it's wise to savor wine nearest where you plan to sleep.
Day 5: San Gimignano & Volterra
This can almost be considered a third day in Chianti because it is so close, but this is a day for white wine: Vernaccia di San Gimignano. Take a respite from cork sniffing in the afternoon and visit the impressive Etruscan city of Volterra (where there's also a fine, cavelike wine bar).
Day 6: Bolgheri
Home to the prestigious "Supertuscan" labels Sassicaia and Ornellaia (Bolgheri DOC), this out-of-the way venue is worth the trip for those who are serious about wine. Book well in advance for a vineyard tour and to stay at a bed-and-breakfast or agriturismo (www.bolgheridoc.com). There are few hotels in the immediate vicinity.
Days 7-8: Elba & Siena
Take a break on the island's beaches -- enjoy its seafood and try a glass of its fish-friendly, crisp white or unique sweet red Aleatico. You will need to organize your ferry in advance in high season. Plan to spend the second afternoon driving to Siena. Resist the temptation to explore one of the back roads as it will take much longer than you think. Instead, do as the locals do and use the highway via Grosseto. (Even if you plan to make a side-trip to Massa Marittima, you'd be well-advised to return to the highway afterward.)
Days 9-10: Montalcino & Montepulciano
Brunello di Montalcino and Vino Nobile di Montepulciano are two of Europe's most prized reds, and the countryside that yields them is spectacular. Some of the producers have onsite apartments for rental, but wine enthusiasts may prefer to stay in one of these historic hill towns, since each of them is essentially built around the wine industry and has plenty of tasting opportunities in the center.
Day 11: Orvieto
Vintners around this hilltop Umbrian city have been cultivating their famous whites since Roman times, but the city itself has its own treasures, gastronomic and otherwise. Explore the ancient tunnels in the tufa rock (which, among other uses, served as medieval wine fridges), and admire its outrageous cathedral.
Day 12: Torgiano & Montefalco
One of the highlights of any tasting trip to Italy is the Wine Museum in Torgiano, near Perugia. It is the only one of its kind, owned and operated by the area's largest producer, Lungarotti. The family also runs a tasting room just next door. Plan your meals in Perugia, or, even better, in Montefalco, which is where Sagrantino, the true gem of Umbrian wine, is to be found.
Day 13: Assisi
No special claims to oenological fame here, but a trip to Umbria must include this spectacular shrine of Christianity. You could spend an entire morning in the Basilica di San Francesco, and then head back to Florence in the afternoon, stopping off in Citta' di Castello, Sansepolcro, and Arezzo along the way.
Day 14: Depart Florence
Visit whichever sights and restaurants you missed the first time around and finish up with some shopping at the city's wine stores, most notably Enoteca Alessi.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
