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.
“Brava Ludmila, bel giro per le strade di Siena, con aneddoti e informazioni utili per comprendere meglio la storia della città e le tradizioni del luogo.”
Private 2–3 hour walking tour of medieval Siena with a licensed guide: Palio stories, St Catherine relics, and Duomo secrets.
“If you want to get an in depth history of Siena and its culture this is a must tour. Our guide was extremely knowledgeable and was an excellent communicator.”
Private Secret Siena walking tour from Piazza del Campo with a guide, free church stops, contrade Palio stories, and flexible timing.
“Sylvia was an excellent guide. She asked where we had been and changed her tour to places we had not been. She was very knowledgeable and personable and we highly recommend her since we experienced a great tour”
Walk Siena with a private local guide, get a custom route, photo stops, and solid museum planning help, plus the Palio context.
“the whole experience was great, really good to get in-depth knowledge on the horse race, the traditions that surround it”
Private Siena walking tour with skip-the-line Duomo entry, contrade and Palio stories, plus optional crypt and museum.
“Giulia was very knowledgeable and made our tour super enjoyable! You can tell she cares about the history of Siena. Our group was very small (4 people) which made navigating the city and lines very manageable. This tour is 1000% worth it!!”
Private tour of a medieval Tuscan castle in Val di Merse, then an organic wine tasting with Sangiovese and international grapes.
“We loved our morning on this tour. We arrived in a taxi from Siena as we didn’t have a car. A perfect host, lovely history and information and experience.”
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.
“Silvia Roncucci was our guide and we had a wonderful tour. She was so knowledgeable and passionate about Siena. Siena is a fascinating city but we would have just walked by so many interesting things if we didn't have a guide. My husband and I felt like we received an amazing introduction to this historical…”
Private Siena day trip to Val d’Orcia and Montalcino for wine, pecorino, Pienza sights, and UNESCO backroad views.
“This was amazing. We went to two wineries. The first had the most incredible views and felt like I was sitting outside of someone's authentic Tuscan home. The second had incredible service and wine with honey tasting! We bought some honey to send home! Then we went to a local farm for lunch which had…”
Private Pienza and Montalcino cheese-and-wine day with organic farm visits, Brunello tastings, and stress-free transport from Siena.
“The tour was great. The organic farm was incredible, with great views around every corner. The tour was educational, both in terms of the cheese making process and the broader farming practice. We got to see some sheep and some young lambs too, which was a treat! It was great with our 18 month old.…”
Private 2-hour Duomo tour in Siena with a local guide, skip-the-line entry, and expert help spotting iconic sculpture and floor details.
“It is so perfectly done and personal. Luda has a vath knowledge of the area and its history. Amazing!!”
