15 Siena Tours to Build a Day Around

1.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164.26Our pick

Florence to Tuscany in one day, with Siena sights, a Chianti estate five-wine tasting, and San Gimignano towers plus a truffle lunch.

“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 $9

Skip-the-line access to Siena Cathedral and the Piccolomini Library, plus a QR audio guide. See mosaics, sculptures, and Pinturicchio frescoes.

“Excellent was able to skip the line to pick up a ticket when we had to hop on our tour bus in 30 min! Inside was one extremely beautiful, enjoyed it better than Vatican”

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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 for all-access entry to Siena’s cathedral complex, plus an audio guide covering crypt, libraries, museum, and views.

“It was a great experience and our guide was outstanding!”

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

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

2-hour Siena walking tour with skip-the-line Duomo tickets, local guide, Palio stories, and Gothic masterpieces inside.

“The tour was wonderful and Ambra really enriched the visit with a lot of interesting stories about Siena and the Palio tradition! We really enjoyed it.”

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

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217.67Top rated

Small-group Brunello di Montalcino wine day from Siena with 3 tastings, a winemaker lunch, and Abbazia di Sant'Antimo.

“Paolo carefully selected the family run wineries that provided us a true grasp of the culture behind creating Brunello wine. The hosts families were so gracious and shared their stories and one even provided a home cooked meal in their home. An incredible day! Paolo was so knowledgeable and shared so many historical facts with his perfect English. Thank you Paolo for a wonderful experience.”

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6.Palazzo Pubblico Entry Ticket

★★★★★★★★★★4.2 · 708 reviews · from $7Best value

A small-group 1-hour ticket to Siena's Civic Museum in the Palazzo Pubblico, from Simone Martini frescoes to Loggia dei Nove views.

“Fabulous collection in an impressive building. The famous fresco by Ambrogio Lorenzetti, “Allegory and Effects of Good and Bad Government” was unfortunately under renovation. Having read A Month In Siena by Hisham Matar, I was eager to view this series of artworks. Nevertheless there was an abundance of significant art, stunningly decorated rooms and incredible architecture. One of the highlights of my Italian trip. Highly recommended.”

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7.Skip the Line: Siena Duomo and City Walking Tour

★★★★★★★★★★5.0 · 689 reviews · 2 hours (approx.) · from $48.37

Skip the line for Siena Duomo, then walk car-free lanes with a guide, seeing contrade, Piazza del Campo, and Gothic churches in English.

“The presenter was engaging and very knowledgeable about the history and a lively rendition of the horse race in the piazza. We thoroughly enjoyed our tour.”

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8.Chianti and Castles Tour with Wine Tastings

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

5-hour Chianti tour from Siena: small 8-person minivan, two winery tastings, Castellina in Chianti and Monteriggioni hilltop sights.

“Beautiful tour through Tuscany and Chianti region. Not really a castle tour but visits to towns with towers and surrounding by walls. Two different but great wine tastings in different areas. Highly recommended!”

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9.Tuscan Cooking Class

★★★★★★★★★★5.0 · 584 reviews · 3 hours (approx.) · from $157.21

Hands-on Tuscan cooking in a San Gimignano farmhouse. Make 5 to 6 courses, fresh pasta, wine pairings, and optional truffle hunting.

“It is so family oriented. You feel like you are being welcomed into an Italian home. Food was amazing! We enjoyed every moment.”

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10.Montepulciano: Wine Tasting and Cellar Tour

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

1-hour Montepulciano cellar tour with 5 DOC/DOCG wines, pecorino cheese, and bruschetta, plus barrel and tufa-soil history.

“This was an incredible tour - so interesting as well as a beautiful place to explore. The wine was incredible!! One of our "core memories" from our trip to Tuscany. We were so glad we booked this tour!”

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11.Siena, San Gimignano and Chianti Small Group Tour

★★★★★★★★★★4.9 · 433 reviews · 9 hours · from $175

9-hour small-group Tuscany day trip from Florence: Siena walking tour, Chianti wine lunch, San Gimignano towers, free time.

“Wonderful experience. Our guide was a delight. Very funny and personable. I’m disabled and he helped to make as many accommodations as he could. Very sweet. He was very informative and I learned a lot about the area.”

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12.Total Immersion Wine Tour in Chianti

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

Total Immersion Wine Tour in Chianti: family-run organic winery, rooftop views, vineyard and cellar lessons, 5 wines plus snacks.

“Put up shades on the roof! Other than that it was a lovely time. We learned a lot- loved the black rooster story! The wine was delicious, the winery is beautiful. It is a challenge to get to- narrow roads, twisty turns, and large rain water ruts! We were concerned getting there about where we were going but afterward we were so glad we did it! The tasting part was especially delightful”

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13.3h Private City Walking Tour with Optional Cathedral

★★★★★★★★★★4.7 · 392 reviews · from $164.26

3-hour private Siena walk with a local guide, UNESCO stops, Piazza del Campo, and optional Duomo entry. Skip lines, photo stops.

“My guide Mare was wonderful! I prefer to be guided as a traveler and want to learn the inside story of a few key places in a city. Mare taught me about Saint Catherine of Siena, the Paleo and all of its details and the Duomo of Siena. I told her I knew how to be guided and she smiled and became good friends which is essential for this type of experience. I highly recommend this tour!”

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

★★★★★★★★★★4.9 · 380 reviews · from $95.16

Guided stroll through Siena’s medieval streets to skip-the-line Duomo access, with an optional OPA SI Pass upgrade for crypt and museum.

“Most liked the fascinating historical points and detail! Most disliked- nothing.”

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15.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203.91

A small-group Brunello di Montalcino day trip from Siena with three winery visits, vineyard walks, tastings, lunch, and Sant’Antimo.

“This was a most excellent day touring the Montalcino region and Brunello wineries with William one of the best guides we have had in Italy. He was full of knowledge of the history of the area and the art of making (and tasting) Brunello. He made the day most enjoyable.”

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