The 7 Best Siena & Tuscan Hill Towns Tours

1.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164Our pick

See Siena, a Chianti estate, and San Gimignano in one full day, with five wines, Tuscan food, and free time in medieval towns.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.”

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2.Siena Cathedral and Piccolomini Library Entry Ticket

★★★★★★★★★★4.5 · 3,462 reviews · from $9Best value

Enter Siena Cathedral and the Piccolomini Library with fast-track access, Renaissance art, marble mosaics, and a phone-based audio guide.

“Very easy just pick up tickets and then head to the entrance, nice and simplistic”

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3.Cathedral Complex Pass with Audio Guide (OPA SI PASS)

★★★★★★★★★★4.4 · 2,773 reviews · from $21

Explore Siena Cathedral, its hidden crypt, Piccolomini Library, museum, Baptistery, and Facciatone viewpoint with a three-day pass.

“You get to do a lot of things within the package & it’s a good bang for your buck. The Duomo, and look out point are so worth it.”

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4.Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Top rated

Taste Brunello at three Montalcino wineries, enjoy a homemade Tuscan lunch, and visit Sant'Antimo Abbey on a small-group day from Siena.

“Visited 3 beautiful family owned wineries and all of the wines were delicious even bought a few bottles to enjoy along our travels in Italy”

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5.Montepulciano: Wine Tasting and Cellar Tour

★★★★★★★★★★4.8 · 545 reviews · 1 hour · from $38

Tour Montepulciano’s historic wine cellar, taste five DOC and DOCG wines, and pair them with pecorino, bruschetta, and local crostini.

“Amazing tour loved very bit of it. Every once in a while I order some wine from the Contucci Cellar. loved it”

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6.A Wine Tour and Tasting Experience

★★★★★★★★★★5.0 · 352 reviews · 3 hours (approx.) · from $102

Tour Siena’s organic vineyards, taste four Tuscan wines, learn winemaking from a sommelier, and enjoy a seasonal lunch at La Lastra.

“Found this wine and food tour and loved it. Beautiful setting in the winery. We toured the vineyard and cellars. Then the wine pairing!!! So good my husband bought a case to take away and one shipped home. Loved the fact that it was organic. Our guide. (Sorry can’t remember her name!) was very knowledgeable and took great pictures of us in the vineyard. Met some lovely travelers and shared food and wine. Two thumbs up.”

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7.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

★★★★★★★★★★4.6 · 324 reviews · 1.5 hours · from $69

Tour a medieval castle near Montalcino, taste three Tuscan wines with a sommelier, and enjoy a traditional three-course lunch.

“We had an engaging time listening to Allessio explain the wine making process and the history of the Tricerchia family and Castle The wine tasting and lunch at the end of the tour was a great finish Gracie!”

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