The 15 Best Siena & Tuscan Hill Towns Tours

1.San Gimignano, Siena, and Chianti Wine Tour

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

Travel from Florence by air-conditioned minibus to Siena, a Chianti winery, and San Gimignano. You get guided context, free time, five wine tastings, olive oils, and a Tuscan meal. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and well timed.

“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

Use your voucher to collect a ticket, then enter Siena Cathedral and the Piccolomini Library. You’ll see Michelangelo, Donatello, and Nicola Pisano sculptures, Pinturicchio’s frescoes, the grand dome, and Siena’s famous marble floor. The digital audio guide works through a QR code on your phone.

“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

Use the OPA SI PASS to explore Siena’s Cathedral complex at your own pace. Your smartphone audio guide explains the Duomo, Baptistery, crypt, Piccolomini Library, Museo dell’Opera, Oratory, and Facciatone viewpoint. The pass excludes the rooftop Gate of Heaven tour and requires voucher exchange at the official ticket office.

“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.Walking Tour and Skip-the-Line Duomo Tickets

★★★★★★★★★★4.8 · 1,116 reviews · 2 hours · from $47

Walk Siena’s cobbled center with an English-speaking local guide, stopping at San Domenico, Piazza del Campo, historic palaces, and the Duomo. Guides such as Elio, Claudia, Giorgia, and Julia bring the Palio and Contrade traditions to life. The cathedral ticket lets you skip the main entry line.

“Our tour guide was informative funny and attentive to everyone’s needs. Highly recommend”

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

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

Spend about nine hours with a small group of up to eight, traveling from Siena to three Montalcino wineries, Sant'Antimo Abbey, and the hill town of Montalcino. Expect cellar visits, Brunello and Rosso tastings, a family-style Tuscan lunch, and guides such as Mattia, Juliana, Paolo, and Emanuele.

“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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6.Chianti and Castles Tour with Wine Tastings

★★★★★★★★★★4.6 · 631 reviews · 5 hours · from $100

Travel from Siena in a comfortable eight-seat minivan with an Italian, English, or Spanish-speaking guide. Visit Castellina in Chianti and Monteriggioni, pause for views and free time, then taste Chianti wines at two distinct estates such as Poggio ai Laghi and Lornano.

“Our guide was knowledgeable, kind and fun which made for a great tour for us all. The activities Chianti wine tasting and villages were with castles were amazing and all fitted into one afternoon so perfect.”

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7.Montepulciano: Wine Tasting and Cellar Tour

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

Spend an hour beneath Montepulciano tasting Nobile di Montepulciano and other Tuscan wines. Your English or Italian guide explains the De’Ricci cellar, tufa soil, and oak aging, followed by pecorino, bruschetta, crostini, and possibly a sixth pour depending on the session.

“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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8.Total Immersion Wine Tour in Chianti

★★★★★★★★★★4.9 · 430 reviews · 2 hours · from $47

At Fattoria di Montemaggio, Francesco, Ilaria, or Stefano leads you from a 600-meter rooftop view through the vineyard and cellar. Learn organic winemaking, taste five estate products, and sample cheese, salami, bread, olive oil, and grappa in a small, personal setting.

“Ilaria is a great passionate guide. She made us a tour of the vineyard and the cellar with clear and lively explanation. Also mentioned some interesting information regarding organic farming. Tasting was great with some food and generous servings. Just a note : no discount on bottles vs retail price.”

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9.3h Private City Walking Tour with Optional Cathedral

★★★★★★★★★★4.7 · 392 reviews · from $164

Walk Siena with a private English, Italian, or Spanish-speaking guide, from Basilica San Domenico through Piazza del Campo and the medieval center. Learn about Saint Catherine, the Palio, and the contrade, then add a guided Siena Cathedral visit if you pay the entrance fee separately.

“Great tour. Our tour guide was very knowledgeable and friendly. Would definitely recommend!”

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10.Siena Walking Tour with Cathedral and Crypt & Museum Option

★★★★★★★★★★4.9 · 380 reviews · from $95

Meet your guide beneath the big tree at Basilica of San Domenico for a 2-hour Siena walk covering Piazza del Campo, the Contrade, Fonte Gaia, and the Cathedral. Choose 3 hours with the OPA SI Pass for the Crypt, Opera Museum, Baptistery, and Facciatone views.

“pur guide Elio was absolutely charming and tailored the tour with great consideration to all members of our small group. We learned about the history, culture and customs of Siena in a very engaging way - the right balance of info and fun! it was a great tour!”

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11.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Travel from Siena in a small minivan with an English-speaking guide such as Marco, Georgia, Paolo, or Daniele. Visit three very different Brunello wineries, taste cellar-aged wines, eat lunch at a family-run estate, and stop in Montalcino and at Sant’Antimo Abbey.

“What a great tour! We visited 3 fantastic wineries and had the pleasure of trying several selections of their wines. And Georgia was a wonderful tour guide; very insightful, knowledgeable, and accommodating. We couldn't have asked for a better day.”

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12.A Wine Tour and Tasting Experience

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

Meet at Azienda Agricola La Lastra outside Siena for a three-hour visit through organic vineyards and the wine cellar. Guides such as Maya and Maia explain grape growing, winemaking, tasting, and food pairing before four wines, olive oil, and a seasonal Tuscan lunch.

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

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

Meet your English- or Italian-speaking sommelier at Castello Tricerchi, stroll through the vineyard, hear the estate’s story, and taste three Tuscan wines with local snacks. Finish with cold cuts, cheeses, handmade pasta, dessert, and coffee in a medieval castle.

“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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14.Tuscany Hills Wine Tour

★★★★★★★★★★4.1 · 323 reviews · from $146

Travel from Siena by air-conditioned bus or minivan through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, explore Pienza and Montepulciano on your own, and hear regional stories from multilingual guides such as Marta, Vincenzo, and Luciano.

“Downside a bit of confusion at the beginning of the trip while waiting for connecting bus from Florence. Communication could have been better. Lastly at the end of the tour the bus dropped us off at night in the outskirts of the city of Siena and it was difficult to find our accommodations from that point. Would have been better to drop us off at La Lizza Bar.”

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15.Discover Siena: Guided Walking Tour and Cathedral Visit

★★★★★★★★★★4.3 · 314 reviews · 1 hour · from $34

Join a live English, Spanish, or Italian guide at Basilica Cateriniana di San Domenico for a short walk through Siena’s Campo, palazzos, and cathedral. You’ll hear about the Palio, noble families, and local saints, then see major works by Pisano, Duccio, Donatello, Pinturicchio, and Bernini.

“Great tour on a hectic day right before the Palio.”

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