Italy · SIENA TOURS
The 15 best siena tours you can book today, with what each costs, how long it runs and who it suits. Number one is first for a reason — start there.
Florence to Tuscany in one day: Siena, Chianti with 5 tastings and lunch, then San Gimignano towers. Guided, small-group tour.
“The guide was very informative and engaging. We had a fantastic day and got what we wanted, history, fantastic surroundings and wine yard.”
Skip the ticket line for Siena Cathedral and the Piccolomini Library. Marvel at Donatello, Michelangelo, and Pinturicchio with QR audio.
“Absolutely amazing!! No words can describe these monumental architectural masterpiece!!”
Siena Duomo OPA SI PASS grants 3-day access to crypt, library, museum, baptistery, and Facciatone viewpoint with a digital audio guide.
“The meeting point was a little confusing to find. It might be helpful to say, the tickets can be found to the left of the entrance of the cathedral in the “reserved ticket line” for exchange.”
Two-hour Siena walking tour with an English guide, UNESCO sights, Basilica di San Domenico, and skip-the-line Duomo entry.
“A great tour of Siena. If you only have a short time in this beautiful city I would highly recommend this tour. We learned so much about the city from our guide, Giorgia, who was extremely knowledgeable and clearly passionate about her city. We loved it, even in the pouring rain! And lunch at Osteria Cice recommended by Giorgia was fabulous. Thank you.”
Small-group Brunello day trip from Siena: 3 winery tastings, family lunch, Sant'Antimo abbey, and free time in Montalcino.
“A very good tour, with a fine lunch and excellent wine. Our guide, Sara, was warm, welcoming and well versed about the region, vineyards, wineries, and wine produced in Montalcino. We were served three selections from Tricherci, a table wine, rosso and brunello. We enjoyed them all as well as noting the differences between them. The others on our tour provided good company for a fine day.”
Skip-the-line access in Siena plus a 2-hour guided walk through the contrade, Piazza del Campo, and an art-filled Duomo visit.
“Fantastic Tour! A must do if you want to have a basic understanding of Siena. Our guide Elio was was informative and funny.”
Half-day Chianti tour from Siena with a small-group minivan ride, Castellina and Monteriggioni stops, plus two winery tastings.
“Fabulous tour with great local insights into culture, wine and food. Highly recommended”
Small-group day trip from Florence to Siena, Chianti wine lunch, and San Gimignano towers, with a guided walk and free time.
“Lorenzo was a fantastic guide and Francesco was a great driver. We had a fantastic time on this tour and loved visiting Sienna, San Gimignano and the Tuscan countryside! Molto bene!”
A 2-hour Chianti Classico tour at Fattoria di Montemaggio, tasting 5 wines plus olive oil and grappa with an English guide.
“Amazing tour, great wine. Francesco is a really nice guide and extremely involved with the winery.”
A 3-hour private walk through Siena’s Medieval center, with photo stops, UNESCO highlights, and an optional guided Duomo visit.
“What a great tour! I learned so much about Siena that I never would’ve known by just walking the city myself. I also loved that it was far more personal given the small size. Seeing the massive tour groups go by made me appreciate this one all that much more.”
Walk Siena’s medieval streets with skip-the-line Duomo entry. Choose a 3-hour option with OPA SI Pass for crypt, museum, and views.
“Very knowledgeable guide. Lots to see. Definitely include the Duoma and Cryptic. Was worth the additional cost!”
Brunello di Montalcino from Siena: small-group minivan tour with vineyard walks, cellars, Sant’Antimo Abbey, and a family lunch.
“Paolo is an excelente guide . He is knowlegdeable, pleasant, and great driver . Time went fast. We will book the activity again !”
Full-day Tuscany wine tour from Siena with two cellar tastings, Chianti and Nobile di Montepulciano, plus time in Pienza and Montepulciano.
“Only problem was the bus dropped us off in an area we did not recognize but luckily others in the group knew where we were.”
Walk Siena’s landmarks with a local guide, learn the Palio and noble families, and visit Siena Cathedral with included entry.
“The tour was very informative and the local guide was excellent. We learned much about the history of Siena and also about the local culture and life inside the city.”
Make fresh pasta and classic tiramisu in Siena at Trattoria Fonte Giusta, with Prosecco, wine, and a hearty meal, in 3 hours.
“The guide, the chef, everything was fun and we met new people”
Every kind of day out in the country, and the best of each.
