TUSCANY
Most booked first.
Our shortlist of the 10 most-booked private tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.
Private 3-hour walk through medieval Siena from San Domenico to Piazza del Duomo, with Palio/Contrade stories and optional cathedral access.
“Great tour. Our tour guide was very knowledgeable and friendly. Would definitely recommend!”
Private 2–3 hour walking tour of medieval Siena with a licensed guide: Palio stories, St Catherine relics, and Duomo secrets.
“We had a lovely day with Barbara! Learned so much but not too much. Pleasant and highly knowledgeable. There is a lot to Sienna and we would have missed so much. Highly recommend!”
Private Secret Siena walking tour from Piazza del Campo with a guide, free church stops, contrade Palio stories, and flexible timing.
“Wow, just awesome. Georgia was outstanding. We even booked her for another tour later in the week. This was the most enjoyable part of the vacation…we learned so much…i highly recommend this tour!”
Walk Siena with a private local guide, get a custom route, photo stops, and solid museum planning help, plus the Palio context.
Private Siena walking tour with skip-the-line Duomo entry, contrade and Palio stories, plus optional crypt and museum.
“Susanne was excellent! Gave the right amount of information on the history, culture, traditions and of course food in the region. A gentle pace walking around some of the amazing streets in this living museum city. The Duomo certainly stands out Definitely enriched our stay.”
Private tour of a medieval Tuscan castle in Val di Merse, then an organic wine tasting with Sangiovese and international grapes.
Private 2-hour Siena walking tour in English with Palio stories, Piazza del Campo sights, and Duomo-area views for one group up to 15.
“The tour was great. Silvia was helpful, showed us around, answered all of our questions and was, in general, an awesome tour guide. I’m not a fan of Viator but feel very lucky that Silvia was our guide.”
Private Siena day trip to Val d’Orcia and Montalcino for wine, pecorino, Pienza sights, and UNESCO backroad views.
“We had a wonderful experience with Roberto. 2 wineries and a lunch at a sheep farm that was marvelous. Local meet and cheeses and we even got to see the sheep. Then a stop in Pienza for some sightseeing and a lovely drive back to our hotel. First class experience.”
Private Pienza and Montalcino cheese-and-wine day with organic farm visits, Brunello tastings, and stress-free transport from Siena.
“This was the perfect tour to experience the wine and cheese of the area. Our guide, Daniele was very knowledgeable and friendly!”
Private 2-hour Duomo tour in Siena with a local guide, skip-the-line entry, and expert help spotting iconic sculpture and floor details.
“Barbra had an incredible wealth of knowledge about the Cathedral and Siena. As an art historian, she was the perfect guide.”
