Top Siena Day Trips - page 3
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What are people saying about Siena
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!
Jacky_Y, Apr 2026
Informative walking tour with knowledgeable guide
We decided to go to Siena last minute and found a walking tour on Viator. Booking process was very easy. On the day of the tour, it was taking longer than expected to find parking and my husband dropped me and my son off first. Our tour guide Sylvia was very nice and started the tour slowly so my husband and my daughter could catch up. She was also very knowledgeable and patient to answer any questions we had. Just one thing though- the big tree in front of the Basilica (the meeting point) has been chopped off, so maybe Viator or the tour operator should update the description to avoid any confusion.
Maryanne_Y, Apr 2026
Excellent adventure
Georgia was our guide- she was fantastic and shared so much information and insights with us along the way. History, culture, architecture and answered every question we had including restaurant and wine recommendations. The day was special- we saw a lot. Highlight was meeting Homero- the alabaster craftsman. What talent at 83! And just adorable. This is a must do tour. Thank you Georgia!
Janet_B, Nov 2025
Highlight tour of Tuscany
Guiliana is an expert guide, making our trip so interesting. She is an absolute rock star! She knew so much history about the area and answered any questions we had. The views through the winding roads on our trip to Pienza and Montepulciano were spectacular. After stopping for a cappuccino in a little town along the way, we were able to explore Pienza. It rained during our time there, but we made the best of it by having a delicious lunch at a nearby cheese farm, Podere Il Casale. We were served various cheeses to try from mild to very strong, salad, and a pasta dish. Perfect. We also learned about the differences of olive oil. With our bellies full, we headed to wine tasting at the Gattevecchi winery. We were given a tour of their wine cellar, too. Even though it was raining really hard, we still managed to walk through the town of Montepulciano. This tour is a must if you want to learn more about the Tuscany region. Be sure to ask for Guiliana as your guide!
Jay_S, Oct 2025
Wonderful Tour, Great Guide!
Our tour guide, Giorgia, was very personable and knowledgeable. We learned a great deal about Siena and a short amount of time. A highlight was Giorgia's expertise regarding the Duomo pavement art. Truly fascinating. The pace of the tour was perfect and Giorgia walked the streets discussing it's history and views with patience.
James_M, Oct 2025
Adventure in Tuscany
Just a nice time. Constantino ( I believe that was his name) was informative, passionate and funny. Much Enjoyed lunch and wine in Tuscany winery. The only (small) issue I had was the tour had English and Spanish translation. You should separate the 2 audiences (thought Constantino handled it well!)
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!
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.
Hannah_N, Sep 2025
Great Tuscan experience
I'm so glad I chose to book this at the last minute. La Lastra winery is stunning and picturesque, just what I pictured when I planned a visit to Tuscany. Maya was a knowledgeable and warm guide who gave us lots of engaging information about the wines and answered our questions. The homemade meal and wine tasting was a highlight. And it wasn't awkward at all going along solo.
Smokey_Y, Jul 2025
Great Class
I have had cooking classes on several international trips to include a previous to Italy and trips to Morocco and Spain. All were great experiences but this was hands down the best. The food was great but the multi-lingual aspect along with cultural insights made it truly memorable.
Allan_B, Jun 2025
Enrich your stay at Siena
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.
David_C, May 2025
Lovely day and easy...
Lovely day and easy itinerary - starts early but it's for the best - starting in san Gimignano before crowds arrive, then moving on to a great winery - lunch is an option there, unless you're bringing food or buy something to go in san Gimignano, this is really the only lunch option so I recommend it.
The tour itself is a nice mixture of walking and wine interspersed so you never feel overly tired. Vincenzo was an excellent guide and really added a lot of history to what we saw. Great day overall highly recommend
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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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