5 Siena Cheese Tours Worth Flying For

1.Pienza, Val d’Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

★★★★★★★★★★5.0 · 36 reviews · 8 hours (approx.) · from $527Our pick

Leave Siena with a private guide such as Roberto, Dario or Davide for an eight-hour tour through Montalcino and the Val d’Orcia. Expect wine tasting, Pecorino cheese, scenic backroads, a stop in Pienza and flexible time for local food or extra stops. Pickup and drop-off are included.

“This was the most amazing experience. Roberto was incredible. Knowledgeable, friendly and genuine. Highly recommend the experience and Roberto!”

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2.Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

★★★★★★★★★★5.0 · 31 reviews · 8 hours (approx.)

Spend about eight hours with a private English-speaking guide visiting an organic dairy near Pienza, Renaissance Pienza, and a Brunello winery in Montalcino. Guides such as Daniele, Georgia, Matteo, and Ambra bring local wine and farming knowledge. Pickup is offered, lunch is on your own, and only your group participates.

“Wonderful day with our guide, Georgia. She has a wealth of knowledge and fabulous sense of humour. Made our day informative and fun! Can’t recommend this tour enough!”

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3.Cities, Cheese and Wine Tour in Pienza & Montepulciano

★★★★★★★★★★5.0 · 24 reviews · 6 to 8 hours (approx.) · from $601

Spend 6 to 8 hours with an English-speaking driver-guide visiting Montepulciano, Podere Il Casale, and Pienza. Taste Nobile wines in historic cellars, enjoy a cheese-farm lunch with views, and ride in an air-conditioned vehicle from Siena or the Chianti area. Guides may include Stefan, Stephan, Masi, or Leo.

“Stephan was an amazing guide and driver for our day. He knowledge about the region made our day fun and informative. We would highly recommend this tour and exploring the hidden gems.”

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4.Visit to the Bufale and Dairy farm with cheese tasting

★★★★★★★★★★4.5 · 13 reviews · 1 hour 30 minutes (approx.) · from $78Best value

At La Maremmana, an agronomist leads you through the dairy, buffalo enclosures, and biogas plant before a tasting of cheeses made with milk from the farm. You can watch production through a glass window, see calves in spring and summer, and sample the cheeses with salami and local wine. The 90-minute tour starts at 9 a.m.

“Very interesting and a fun tour for all of the family. The tasting of the food/cheese was delicious!!”

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5.Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

★★★★★★★★★★5.0 · 10 reviews · 8 hours (approx.) · from $565

Spend about eight hours with a private driver-guide, such as Roberto, traveling from Florence into the Val d’Orcia. Visit Capanna di Cencioni for Brunello tasting, explore Pienza, stop for photos, and enjoy a flexible day with Wi-Fi, refreshments, and door-to-door transport. Lunch costs extra.

“We had the most amazing experience exploring the beautiful wineries of Siena! Roberto truly knocked it out of the park with his charisma and incredible knowledge & passion for the local wines, giving us wonderful stories and background. We specifically love Brunello from Montalcino, and this tour gave us an excellent taste! He also took us to the most beautiful little UNESCO certified inn for a delightful lunch, with the quintessential Tuscan view and experience. Absolutely delightful experience- would highly recommend if you are a wine lover!”

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