Top Siena Day Trips - page 2
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What are people saying about Siena
Jonathan_G, Jun 2026
10th Anniversary Trip
Was so pleased with this experience. The chef, Francesco (and translator) were both so patient, explaining everything and going at a pace that everyone could learn. The food was AMAZING, and the techniques taught will be able to be used back home. Highly recommend for a relaxing and delicious meal!
Catherine_D, Jun 2026
Tutto benissimo
10/10 would recommend. Keko was a knowledgeable and charismatic tour guide. While we drove through the Tuscan countryside, he provided engaging commentary about the history, the landscape, and the local food traditions of the region. If you want to see the Tuscan country, this is the way to do it.
I particularly enjoyed the lunch at the farm and tasting the local recipes with ingredients made right there. The time in Pienza and Montepulciano flew by. I would definitely take this tour again.
Michele_H, May 2026
Tour of San Gimignano and Volterra
After days of walking 9-10 miles it was nice to relax on this tour. It was a great trip with a knowledgeable guide. Each stop was amazing with beautiful views of ancient towns. The lunch on the family farm was delicious. The hostess grows her own olives and saffron and prepares a wonderful meal using these ingredients. She also uses these to make soaps, olive oil and lotions.. The alabaster shop was interesting, and here we bought a beautiful bowl to take home. You won’t regret this tour.
Dasha_C, May 2026
This is a must-do in...
This is a must-do in Siena. Georgia was an amazing guide who packed so much information into the two hours while keeping things lively and interesting. We were there on a national holiday so the city was very busy yet she navigated our large group around the city easily.
Madeleine_R, Apr 2026
So much fun! The farm was...
So much fun! The farm was a definite highlight -- gorgeous views and incredible snacks to kickstart the day! We loved getting to walk around Pienza, and the wine was incredible (though definitely pricey if you wanted to purchase bottles to ship home). All in all a perfect way to explore Tuscany. We also loved our guide Frederico! The perfect balance of informational and letting us relax without pressure.
Kelly_M, Apr 2026
Siena Ebike Tour
Giacomo was fantastic as our guide. He was friendly and patient and full of information. We were happy to have him as our guide and you can tell he really loves what he does. The weather was perfect and the winery for lunch and wine tasting was amazing. Thank you Giacomo!
Bonnie_S, Nov 2025
A day in Chianti, Siena & San Gimigniano
The tour was very well organized and managed by Sandro who led the group through the history of this part of the Chianti region. He was very knowledgeable & pleasant.
The lunch was delicious & accompanied by tasting of 2 types of Chianti wine & a vin Santo.
Lucia, the guide to the Siena cathedral, was excellent & very thorough
Andrea_B, Oct 2025
Perfect Overview of Siena!
Perfect overview of Siena! Giulia was an engaging guide! It was a great pace and we loved learning about the contrate, Palio and Duomo. Giulia kept us engaged annd was very knowledgeable. She moved at our pace was very accommodating. I would recommend going in the duomo. It’s worth the $ and time!
Christine_D, Sep 2025
Book this tour!!!
I cannot imagine a better tour guide than Elio. He took the time to shape the tour around our interests. It was far more than we hoped for. Elio gave us insight into the Basilica, the contrade, and even shared his expertise in Tuscan wines. He has a command of history, religion, art history, and Siena culture. We had the most excellent morning seeing Siena through his eyes.
Janice_K, Sep 2025
Excellent wine tour
If you are looking for an all-day wine tour that visits more than one winery this is a great option. The tour stops at three wineries. The first two were my favorite. The second tour included an excellent lunch. Our driver/host was knowledgeable and explained the pyramid of wines and we traveled. He was very courteous and gave the group options on how long we wanted to stay.
Janice_F, Sep 2025
Wonderful evening with excellent performances.
Acoustics were wonderful. Singers and pianist were excellent, very expressive. A small facility but the staff were very well organized. Our seats were easily identified with our name. A good selection and mixture of songs. Loved the evening experience.
Donna_W, Jun 2025
Great Tour for sightseeing and wine tasting
Great tour. The castles and the wineries were great. A lot of different wines to taste, but also gained knowledge of the region and the winemaking process. Just one warning. If you get car sick easily, make sure you bring your remedy. The roads are curvy and bumpy.
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Thanks to its prime location in central Tuscany, Siena is an ideal base for exploring the wider region. Siena day trips cover a range of destinations—from the medieval hill towns of San Gimignano and Monteriggioni to the wine capitals of Montepulciano and Montalcino—and save you the hassle of piecing together tricky logistics yourself. Relax with private transport and experience the best of Chianti and the Val d’Orcia, focusing on the villages and castles or sipping your way through the region’s wineries. You can even channel the dolce vita vibe with a classic Vespa or vintage Fiat 500 excursion.
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