Fall is the perfect time to sip your way through Italy. Many choices are available from week-long tours to day-trip jaunts from Florence, Milan or Rome out into the surrounding wine regions.
For example, if you want to spend a week indulging in Tuscan wines, Premier Vineyard Tours serves up a seven-day sojourn from Sunday, October 5 to Sunday, October 12 during which time you’ll treat your palate to a sampling of the region’s Chianti, Brunello, Montalcino, and San Gimignano wines.
A birdseye view of the tour looks like this: You’ll fly into Florence where you’ll be picked up and transported to a villa/farmhouse near San Gimignano. By happy hour you’ll be greeted at a special villa reception and mingle with other guests. Next, you’ll go to a nearby winery for a tour and tasting with dinner following in a village osteria.
  Chianti Classico sign 

  Chianti Classico sign 

On day two, after breakfast at the villa, you’ll visit the Chianti Classico region and one of the oldest family-owned wineries in Tuscany. Well, you get the idea, you’re here to enjoy local wineries and food and that is exactly what you’ll do. The tours are not inexpensive and cost €3200 per person [double occupancy] and airfare to Florence is not included. But the package includes six winery tours, all meals except two dinners, a cooking class and ground transportation, so you aren’t left with a lot of details to handle or incidental expenses.  For more information visit premiervineyardtours.com.
October in Umbria Italy is also a perfect choice. Why? In addition to wines, Perugia hosts the Eurochocolate Festival from October 17 through October 26. This is more than a little village street fest; this is the largest chocolate festival in all of Europe.
An estimated 900,000 people visit this one-of-a-kind tribute to chocolate and competition for accommodations is what you might expect. However, early out on Expedia.com you’ll find 3-star and 4-star rated lodging options for around $100 per night. For instance the Castello dell’Oscano satisfies guests with rooftop terrace, pool, fitness facility, sauna, complimentary wi-fi and complimentary breakfast starting at $96 per night.
The Relais & Spa La Corte Di Bettona-Umbria can be booked for as little as $88 per night. Here you will find more old world charm from its arched brick and beamed ceilings as well as a contemporary spa and fitness center.
  Montefalco, Umbria, sorrounded by sagrantino vineyards

  Montefalco, Umbria, sorrounded by sagrantino vineyards

But back to wines, Perugia is home of Umbria’s stellar red wines including the Sagrantino di Montefalco wines made from black grapes grown on the hillside vineyards of Montefalco. You’ll also want to try the Torgiano Rosso Riserva from the Lungarotti winery in the Umbrian village of Torgiano. The village of Orvieto produces a crisp, peachy white that is the best-known wine in Umbria. 
The above mentioned Umbrian wineries can be booked through cellartours.com, a service which also organizes luxury wine tours in virtually every region of Italy including Rome, Milan, Siena, the Amalfi Coast, Taormina, Verona, Tuscany, Florence, Piedmont and Sicily. Pricing varies and, for examples of itineraries, visit their Web site.
Picking an agritourism location is a choice that many enjoy. The site agriturismo.net offers a variety of choice accommodations that provide farm/villa lodging in areas close to wineries. You can also select by truffle tasting or specifically wine tasting in Tuscany. This is a site that opens up the countryside of Italy and lets you tailor exactly the type of country vacation that you would enjoy. It also includes listings complete with photos, pricing and discounts.
For example Strada del Vino dei Colli di Candi e di Lunigiana is the wine road of the Candi and Lunigiana hills, the northernmost such road in Tuscany. It borders the Emilia Romagna region on the northeast and Liguria on the northwest. You can drive from Pontremoli to Fosdinovo home of the “Castello di Malaspina”. Then, go on to Carrara, famous for its marble, and on to Massa, where is located another castle and the famous church of “San Rocco”. You wind up in Capanne, located where the light, white Candia wine is produced.
For detailed information on wine roads in Tuscany check out Toskana.net where you can wade through a list of wine roads and what to expect along each of them. There are 14 in all and remember, these are just those exclusive to Tuscany.
What if you don’t have seven days to revel in wine tasting? As mentioned earlier, you can take a day trip from most of the major cities. If you have an extra day in Rome, you can take a guided tour out to the Frascati Vineyard, the Pallavicini Vineyard and to olive groves.  Frascati is one of the oldest vineyards in the area and the drive out is scenic. Through the viator.com site the cost for this day tour will only set you back $80.00.
While fall in Italy offers a world of cultural opportunities, simply sipping wine, sampling chocolates, tasting olive oils or truffles can become the centerpiece of a very enjoyable itinerary that’s also steeped in historic sites and stories.

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