Top Siena Day Trips - page 2
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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.
Lori_S, Sep 2025
Wonderful experience....
Wonderful experience. Loved visiting small family owned/operated wineries. People were exceptionally friendly and hospitable. Julia was a lovely guide. Lunch, cooked by”Mama”, was beyond imagination. This day will go down as one of the best of our Italian holiday. By the end of the day I felt like we had been with family.
Alexandra_S, Aug 2025
Incredible experience
My fiancé and l had the most incredible experience at this Tuscan cooking class. From the moment we arrived, Francesco and Giulia made us feel completely welcome. They are not only warm and kind hosts, but also so knowledgeable about the traditions and techniques behind Tuscan cuisine. Every step of the class was hands-on, fun, and full of little tips we’ll definitely take home with us.
The dishes we prepared together turned out to be the best food we had during our entire stay in Siena—fresh, flavorful, and made with precision. Sharing the meal at the end with the other couple in the class felt like dining with friends rather than in a class. We left with full hearts (and full stomachs!) and cannot wait to recreate these recipes in our own kitchen.
If you’re in Siena, this is an absolute must-do experience.
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.
Lauren_M, May 2025
Discovered Tuscany
Our driver was so friendly and knowledgeable about the region. The itinerary was put together so well giving us time to explore yet keeping us moving along to view four towns. Starting in San Gimignano, moving onto the winery in Chianti for our first tasting with lunch. We learned a lot about the wine and the region. We shared a Great experience with one other couple who we just met that day.
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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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