Siena · PRIVATE
14 reviewed
Here is what to book: the 14 private tours worth booking near Siena, each with what it costs, how long it runs and the one thing to know before you commit.
3-hour private walk in Siena with a guide. Explore Piazza del Campo, palazzi, San Domenico, and optional 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.”
Private 2–3 hour walk in Siena with a licensed guide: San Domenico, Piazza del Campo, Palio contrade, and the Duomo plan.
“Personal, insightful & helpful. Pit guide was knowledgeable & relatable. We enjoyed our time with Julia.”
Private organic wine and oil tasting with lunch at Podere La Marronaia in San Gimignano, with Vernaccia, oils, balsamic pairings, and views.
“The hosts were extremely friendly and the location was beautiful. Phenomenal home cooked food. Wine and Olive Oil made in house. Couldn’t recommend this enough”
Private 3-hour walk through Siena’s secrets with a guide: contrade stories, free churches, and panoramas from Piazza del Campo.
“Elio was a fantastic tour guide - he was super informative, funny, and high energy. Would 100% recommend! We were unsure about a 3-hour tour but it went by so fast because we had such a good time!”
Private custom Siena walking tour with a local guide. See key sights and Palio stories, get food tips. From $65.
“With only one day to visit Siena, this tour was filled with color, history and an extensive traverse of the city inside the wall. It provided us with the opportunity to learn about Siena and all that it had to offer us to do following the tour. Our guide spoke wonderful English.”
A private cellar tour and 1.5-hour tasting at Paradiso di Cacuci in Montalcino, featuring 5 wines including Brunello, plus Tuscan appetizers.
“Marius our guide is so passionate and knowledgeable about the wines. We had a great experience with the amazing Brunellos and the wonderful platter of meats and cheeses.”
Private 2-3 hr walk through Siena’s squares to the Duomo with skip-the-line entry, contrade Palio stories, plus optional crypt.
“We have a very good tour guide and a small group. Would highly recommend when visiting Siena. Got allot of inside information of the city's past and current.”
Private Chianti and countryside wine tour from Livorno with winery cellar access, olive oil tasting, and easy round-trip transfers.
“Our driver Carlo from Prestige Picked us up on time and was such a gentleman and so knowledgeable- He stopped at the right places and took pictures of us and wanted us to be happy with everything- and kept asking about our feedback- The winery was amazingly beautiful and the girl Giovannia was so knowledgable as well and so accommodating- truly an experience to remember”
Private 2-hour San Gimignano tour with an English local guide, medieval towers and piazzas, optional Duomo and Town Hall, views.
“Just liked how passionate tour guy richard was about the town it was beautiful … quaint and nice history story”
Private tour at Castello Poggiarello near Siena: Renaissance chapel and gardens plus organic wine tasting with snacks in 2 hours.
“The tour was excellent. Elena is very passionate about the castle and the wine. It was really nice to learn about the castle and the property. The wines were lovely and not typical of the region. It was a great wine tour that was unconventional and not a cookie cutter experience. Thank you for a wonderful afternoon, Elena!”
Private 2-hour Siena walk in English: San Domenico, Piazza del Campo, Duomo exterior, Palio stories, and the world’s oldest bank.
“Silvia was a very friendly, knowledgeable and talented guide. We'd been to Siena before and had stayed right in town, but had explored on our own with the help of guide books. We welcomed the opportunity to visit Siena again, and were extremely grateful for our time on tour with Silvia. She explained facts, history and a personal perspective on Siena that we'd not have otherwise received. She was flexible with scheduling and gave us great recommendations for the rest our day's visit back in Siena.”
Private tasting day from Siena to Val d’Orcia and Montalcino, with wine stops, quick Pienza time, and guide-led photo 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 the most wonderful hosts, incredible food and an authentic Italian countryside vibes. Finally we did a tour of Pienza which is simply the loveliest city with beautiful views. Out guide, Roberto was funny, friendly, knowledgeable and kind. We loved this!”
Private Pienza and Montalcino tour from Siena with organic cheese tastings, Pienza Renaissance time, and Brunello cellar wine stops.
“The activities of this tour are perfect for my family( all adults ) . The wines and cheeses are excellent! The owners and staff of both the farm and winery are so hospitable and friendly making the tours very memorable for us . No photos can capture the beauty of Val D’Orchia , you have to visit and see it with your own eyes. The vehicle provided by the company is very comfortable and our guide Marella is professional and friendly. She showed up punctually at the time of our tour and put in extra time so that we need not rush through the last segment of the tour.”
Private wine and extra virgin olive oil tasting on a biodynamic farm near San Gimignano, with organic samples, views, and family hosts.
“Amazing experience! The wine, olive oil, food, and setting were all beyond expectations. Dario provided a friendly and knowledgeable presentation of our wine and olive oil tastings. And I have to mention their cute dogs! My photos capture the beauty of their vineyard/farm and San Gimignano. If you would like a Tuscany tasting experience, include this on your journey!”
