Southern Tuscany Food and Wine Tour

The Southern Tuscany, boasts some of the most prestigious wineries of Brunello and Rosso di Montalcino wines.

Southern Tuscany, the Val D’Orcia region is the iconic landscape of Tuscany. This is land that has inspired artists and writers from the world over, as well as the setting for some of cinemas finest films: The English Patient, Gladiator, La Vita e Bella and Romeo and Juliet to name a few. Our 4 day program will introduce you to the beauty and history of the place as well as its culinary specialties; the superb wines of Montepulciano and Montalcino, and the Colli Senesi the cheese of Pienza. A cooking lesson with our local chef will bring it all together as you prepare a full meal with the best ingredients accompanied by local wines. This program can be combined with any of our other programs and is especially suited to combine with our Delights of Chianti program.

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DAY 1 — Arrival in Tuscany

Today you will arrive in the medieval town of Siena and relax at your accommodation. Transfers from your point of arrival can be arranged.

DAY 2 — Siena and the Colli Senesi

This morning visit of the Siena with a private guide. The walk will not be too physically challenging, and will offer a new and entertaining way to become familiar with the extraordinary beauty of this medieval town. Your route will take you away from the ordinary tourist routes, as your guide illustrates Siena’s eventful past through tales of bankers, pilgrims, artists and Saints.
In the afternoon, you will depart with your driver to the Arno Valley to experience the Colli Senesi. You will arrive at a local winery for a truly unique ‘tasting tour’. Beginning in the Enoteca, the first wine will be accompanied by an oil tasting and an explanation of the peculiarities of the area that combine to make the wine’s distinctive flavor. The second wine tasting will be sampled in the cellars themselves, paired with salami and goat cheese, as your guide explains the importance of the different types of earth on which the vineyard is cultivated.At the end of the tour, your driver will drop you off at your hotel.

DAY 3 — Tuscan Cooking class and Brunello wine

This morning a private cooking lesson in a typical Tuscan restaurant has been organized for you. You will create a full menu from appetizer to Dessert. You will then of course enjoy what you have prepared along with a nice lunch. In the afternoon depart with your private driver for Montalcino. Your first stop will be Abbey of Sant’ Antimo, if you are lucky, you’ll be in time to hear the Gregorian chanting of the resident monks. You will then proceed to a localwine estate where you will enjoy an extensive cellar tour. At the end or the tour you will taste 3 different wines including the famous Brunello. Your driver will return you to the hotel in the late afternoon.

DAY 4 — Nobile wine and Val d'Orcia

This morning your driver will take you to the medieval town of Monteulciano where you will have time to wander around this picturesque, walled hill town and see its Gothic and Renaissance architecture. The real reason for your visit however, is the town’s famous Nobile wine, a mellow-flavored red with a mildly floral aroma that features a distinctive iridescent orange tone. Visit of a local cellars with wine tasting and light lunch. In the afternoon continue to a drive through the picturesque Val d’Orcia and the village of Bagno Vignoni. Return to Siena and your accommodation at the end of the tour.

DAY 5 — Departure

After checking out of your hotel, departure for your onward travel. Transfers can be arranged to your next destination or to the airport or rail station.


  • Siena 4 nights


  • Private guided walking tour of Siena
  • Private excursion to Colli Senesi
  • Private excursion to Abbey of Sant’ Antimo and Montalcino
  • Private excursion to Montepulciano, Val d’Olrcia and Bagno Vignoni


  • Private transfer from city to city as per itinerary with English speaking drivers


  • Breakfast at hotels daily
  • Welcome dinner with wines at hotel
  • two wine tasting during Colli Senensi drive
  • Cooking class followed by lunch
  • Wine tasting in Montalcino
  • Wine tasting in Montepulciano


  • Assistance from our Road to Italy office in Italy and local representative offices throughout Italy
  • Local emergency contact number daily

Does not include

  • Airfare(s)
  • Travel Insurance (highly recommended)
  • Tips and gratuities to drivers and local guides


Cities Visited:

  • Siena
  • Montepulciano
  • Val d’Orcia
  • Bagno Vignoni
  • Montalcino

Private Tours

Food and Wine Tours

Request your Free Tour Consultation 1-800-848-8163 or 1 Minute Form Online.

For a quote on this tour please contact us

1 800 848 8163
The price is customized based on final hotel choices, travel dates, and other custom preferences.