15 Tours in Siena Worth Booking

1.San Gimignano, Siena, and Chianti Wine Tour

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

Travel from Florence to Siena, a Chianti winery, and San Gimignano in about nine hours. Expect an air-conditioned minibus or coach, multilingual guidance, five wine tastings, Tuscan specialties, and free time in both medieval towns. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day clear, friendly, and on schedule.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

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2.Siena Cathedral and Piccolomini Library Entry Ticket

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

Use your voucher at Siena Cathedral’s ticket office, then enter through the fast-track line. Inside, see the marble mosaic floor, Michelangelo and Donatello sculptures, and Pinturicchio’s ten frescoes in the Piccolomini Library. Your ticket opens an official audio guide on your phone by QR code. The visit is self-guided and valid for one day.

“Building to the Lord, in great magnificence and splendour can never be out of the question. I pray that that Romanesque structure and the libraries inspire the faithful until the end of time”

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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 visit Siena Cathedral, the Baptistery, Crypt, Piccolomini Library, Museo dell’Opera, Oratory of San Bernardino, and Facciatone viewpoint. A smartphone audio guide explains the art and architecture at your own pace. The pass excludes the cathedral rooftop and Gate of Heaven route.

“Incredible!! A must do/see while in Florence. And definitely do the Duomo climb if your able. 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

Spend two hours walking Siena with an English-speaking local guide such as Elio, Claudia, Giorgia, or Julia. See St. Catherine’s church, Piazza del Campo, the Contrade, Gothic palaces, and the Basilica di San Domenico, then enter the Duomo with skip-the-line tickets. Wear modest clothing and sturdy shoes.

“Claudia was incredible. Very clear and her knowledge was perfect. Her energy was perfect!”

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

★★★★★★★★★★5.0 · 689 reviews · 2 hours (approx.) · from $48Top rated

Walk from Basilica San Domenico through Siena’s contrade, Piazza Salimbeni, Piazza del Campo, and Palazzo Chigi Saracini before entering the Duomo with a guide. Guides such as Elio, Claudia, Julia, and Daniele are praised for lively local stories, especially about the Palio and Siena’s art.

“This is an excellent tour to learn some of the history of Siena and the Duomo. Our guide was amazing and an art history major.”

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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, climate-controlled minivan with up to eight people. Visit Castellina in Chianti and Monteriggioni, stop at two wineries, and taste Chianti wines with Tuscan snacks. Guides such as Fabio, Daniel, Tsvetelin, and Momo add local history and practical insight in English, Italian, or Spanish.

“The viewing points that Chico showed us were great, especially with the autumn colour to the trees and they showed off the Chianti area superbly. The tour of Lornano winery and the tasting were delightful, as were the wines and snacks at Poggio Al Laghi. Our hosts were brilliant.”

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7.Montepulciano: Wine Tasting and Cellar Tour

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

In Montepulciano’s car-free center, a guide such as Mirko, Debi, Emilio, or Ron leads you through historic underground cellars, explains Nobile di Montepulciano and local tufa soil, then serves five DOC and DOCG wines with pecorino, crostini, and bruschetta.

“We loved our tour, we have been on many wine tours and this was up there with the best.”

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8.Total Immersion Wine Tour in Chianti

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

At Fattoria di Montemaggio, high in the Chianti hills, Francesco, Ilaria, or another member of the family team leads you through the vineyard, cellar, and wine-tasting room. You’ll learn about organic farming, Chianti Classico’s Black Rooster, wine tasting, grappa, and five estate products served with local snacks.

“the guide was very freindly and he really created an experience we will not forget.”

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9.3h Private City Walking Tour with Optional Cathedral

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

Spend three hours exploring Siena with a private English, Italian, or Spanish-speaking guide. Visit Piazza del Campo, Palazzo Pubblico, San Domenico, and the Duomo area while learning about Saint Catherine, the Palio, and the Contrade. Add the optional cathedral visit for more art and marble, but pay its entrance fee separately.

“We spent 6 days in Italy - 2 of them in Siena and this tour was the best part of our trip! It was small, informative and we had the best tour guide we could ask for!”

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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 and Cathedral visit, or choose 3 hours with the OPA SI Pass. Expect the Palio, Contrade neighborhoods, Piazza del Campo, Piccolomini Library, Crypt, Museum, and Facciatone views. Guides may include Flo, Dace, Anna, Elia, Sabrina, or Susanna.

“We had booked a group tour but were pleasantly surprised that we were the only two on the tour. Our guide, Daca, was truly extraordinary. She is a native of Siena and truly understands the history, culture, and essence of this magnificent city. She is both knowledgeable and passionate. Her ability to convey the history of the city, to discuss its culture through its district organizational structure, and to interpret the significant art of Siena was amazing. We will always remeber our amazing day in Siena with Daca.”

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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 to three Brunello wineries, Montalcino, and Sant’Antimo Abbey. Expect cellar visits, tastings, a family-run winery lunch, and plenty of Tuscan scenery. Guides have included Marco, Georgia, Paolo, Daniele, and Giulia.

“All around a terrific day. Thought the tour might be too long, but time flew, wine was amazing, lunch delicious and Mattieo, a former vintner, was extremely knowledgeable and passionate about Tuscany and the wine and olive oil that it produces. Highly recommend!”

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12.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 for a vineyard walk, castle and cellar tour, three local wine tastings, Tuscan snacks, and a three-course lunch. Guides such as Alice, Alessio, and Alessandro explain the estate, Brunello production, and food pairings. Arrive 15 minutes early, since latecomers are not accepted.

“Very educational, the wine history and description of the areas and the Brunello and Rossi di Montalcino were very good. Our meal was quite substantial with cold meats and cheeses as well as a small bowl of pasta followed by coffee and small cake. Very historic building with beautiful views. I think it was well done and the young gentleman spoke very good English and was extremely knowledgeable. Steve from Australia”

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13.Tuscany Hills Wine Tour

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

Set out from Siena for a full day through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, then enjoy free time in Pienza and Montepulciano. Guides such as Marta, Vincenzo, Lucia, and Alberto have earned praise for their warm, informative commentary. Lunch is not included, and moderate walking is required.

“One of the best Italian trips I’ve ever been to. To be honest I’m not a fan of wine but the wine provided is good and the cheeses/olive oil/salami are some of the best. Talking about the main travel, you’ll have time to take enough panaromic pictures of this fantastic place. Oh and I must say the lady guide of my group is one of the bests I’ve ever seen.”

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14.Discover Siena: Guided Walking Tour and Cathedral Visit

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

Walk Siena’s historic center with an English, Spanish, or Italian-speaking guide, beginning at Basilica San Domenico and continuing to Piazza del Campo, Palazzo Comunale, noble palazzos, and Siena Cathedral. You’ll hear about the Palio, local saints, and families such as the Piccolomini, Tolomei, and Salimbeni. Guides have included Chiara, Letizia, Claudia, Silvia, and Gemma.

“It was led by a Sienese native. Excellent information. Only wish it could have been longer. There is so much to see in Siena!”

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15.Pasta and Tiramisu Cooking Class with Wine

★★★★★★★★★★4.8 · 274 reviews · 3 hours · from $81

Meet your English-speaking chef at Trattoria Fonte Giusta, toast with Prosecco, and learn traditional egg pasta, pici, gnocchi, and tiramisu. You will eat what you prepare with a glass of wine afterward. Guides such as Dennis and Natalia are patient, lively teachers, and the class works well for solo visitors, couples, and families with older children.

“Lots of fun! Our teacher was great! A good night out with girls as we learnt to make pasta! Definitely a lot of food. Note: Is that you only make the pasta - the restaurant makes the sauce! But they were delicious!”

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