TUSCANY
Most booked first.
Our shortlist of the 10 most-booked guided tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.
Siena’s Duomo complex in one pass: crypt, baptistery, Piccolomini Library, museum, audio guide, and the Facciatone viewpoint for 3 days.
“Helped skip the lines!we were there one day. Stood at the end of the line and decided then to buy the tickets and download . It was easily done and saved several hours of lines”
Small-group Brunello day trip from Siena to Montalcino: 3 winery tastings, a family lunch, medieval town time, and Sant’Antimo Abbey.
“Our guide Marco was so friendly and kind. He told us a lots of useful information of Montalcino wine. And sight seeing was also wonderful”
Guided walk through Siena’s Piazza del Campo, palazzi, and Duomo art with Palio context. Cathedral ticket included for $34.
“This tour was quite short, but definitely informative. Our guide was very friendly and knew a lot about Siena, which was nice. We had a good walk around the center of the city and heard a little bit about many thing. A short introduction to the city”
Walk Siena with a private local guide, get a custom route, photo stops, and solid museum planning help, plus the Palio context.
“Andrea was a very friendly and knowledgeable person. It was a pleasure to learn so much about Sienna’s past and future. She was able to point out the buildings, features of interest and customs. There is a famous annual horse race in August with all 17 neighbourhoods taking place. She will tailor to your interests…”
Guided half-day hike from Siena to Monteriggioni on the Via Francigena, with wine tasting and bus return.
“A nice walk on the Via Francigena, our guide was very friendly and knowledgeabe about flora and fauna. the wine tasting was the perfect end of the tour.”
Siena small-group winery tour at Azienda Agricola La Lastra: vineyard walk, cellar lessons, and tasting 5 organic wines with olive oil and seasonal pairings.
“It's a beautiful vineyard to visit. Wine tasting was varied. The person taking the tour around the vineyard was knowledgeable and pleasant. Food was delicious. A good way to spend an afternoon in Tuscany. The taxi to get there was about 12 euros as of July 2025”
San Giorgio a Lapi guided wine cellar tour with tastings and Tuscan lunch in the hills near Siena; small group, English.
“Beautiful small family vineyard near Siena easily reachable with taxi. Informative tour of vineyard & winery & family church. Friendly & attentive staff. Great delicious lunch with wine pairings, we tried 7 different wines of theirs. Highly recommended.”
Play Siena’s Medieval Power Quest on your phone, solve 9 puzzles at your pace, and see Duomo, Campo and Fonte Gaia.
“App was pretty buggy and difficult to use and English translation and overall story was poor. This was an okay way to walk through old Siena and see some of the major sites.”
Discover Siena in about 1 hour on a guided walk from San Domenico to Piazza del Campo, with optional Duomo entry and museum stops.
“It took a long time before the guide found us. The guide was not inspirated. Our tour was too short.”
A budget-friendly, self-paced audio walk through Siena’s medieval highlights, with local restaurant tips and optional cathedral-area tickets.
“It is a good cheap option, which allows you to tour the city without inconvenience and enjoy the walkAuto-translated”
