San Gimignano, Siena & Chianti Day Trip with Lunch and Wine Tasting
- Discover the historical center of San Gimignano, famous for its tall towers and stunning frescoes
- Enjoy free time in Monteriggioni, a charming medieval village, enclosed by its iconic, well-preserved walls
- Relax at a cozy winery with a tasting of three fine wines, followed by a delicious Chianti-style lunch made from local products
- Explore Siena's historic center with a professional local guide, featuring Piazza del Campo and the spectacular 12th-century Cathedral
What to expect
Your journey begins in San Gimignano, a charming hilltop town known for its tall towers and stunning frescoes. After a guided tour of the historical center, enjoy two hours of free time for exploration. Next, visit the medieval village of Monteriggioni, enclosed by well-preserved walls, where you’ll have free time to explore. Travel through the picturesque Chianti Hills to a cozy winery for a tasting of three fine wines, followed by a Chianti-style lunch featuring local products. In Siena, a local guide will lead you through the historic center, highlighting Piazza del Campo and the 12th-century Cathedral (inside visit if selected). Conclude your day with free time in Siena before returning to Florence in the evening





















Reviews
The itinerary was very well planned. As it was a medieval town, I really enjoyed the historic houses and churches. The guide gave us a satisfactory amount of free time based on the size of each town. This trip felt like an initial exploration of the towns' appearances, giving us a preliminary understanding of their historical backgrounds. The guide was very knowledgeable about these cities and explained their history in great detail. Even on the tour bus, we could admire beautiful vineyards and unique trees. The whole day felt very fulfilling, and time flew by. I highly recommend this trip.
If you want to visit different towns on the same day, it is really recommended to join a one-day tour to save the trouble of transportation links. I didn't particularly want to go to Pisa, so I signed up for this tour. The arrangement of the three towns also requires a lot of walking, so you must wear comfortable shoes and bring water! Fabi is a very cute and humorous tour guide. The introduction of each stop is very exciting, allowing everyone to easily understand the story of the town. Her blonde colleague is very warm and attentive, and the driver who has the best driving skills in the country is also super kind. I like this combination very much~
The tour guide was attentive, and the timing at each attraction was just right. We returned to the meeting point around 6:30 PM. Since we participated in December, we only visited San Gimignano and Siena. Lunch was at a winery where we ate salami, cheese, and Bolognese pasta. The winery provides a wine list, and you can record the flavors of each red wine you drink. In addition to red wine, they also sell balsamic vinegar. After the tour, you can buy wine to take away, and they can help ship it to your home if you are a traveler from the United States or Europe. In summary, it was a very good experience, and travelers without a rental car can easily travel Tuscany with a day trip!
Look for staff wearing blue vests at the meeting point to check in, then board the tour bus with the guide. The guide, Sandro, is enthusiastic and funny and will introduce the attractions along the way. On the way there, sitting on the right side allows you to enjoy the bridge view at sunrise. The Grossa Tower only opens at 11:00 AM. Unfortunately, there wasn't enough time to climb the tower. However, there were very few tourists in the morning, so you can explore at your leisure. Winery lunch and wine/olive oil/balsamic vinegar tasting, with a platter of ham and cheese, and lasagna. Delicious. The guided tour of Siena is led by another local guide. It is recommended to have excellent English listening comprehension before participating, otherwise your understanding will be limited.
Aaron was an excellent guide for our Tuscany tour. He kept everyone well informed about the schedule and timing, guided the group smoothly throughout the day, and made the experience enjoyable with his great sense of humor. He was friendly, organized, and made the tour both relaxing and fun. Thanks to Aaron, we had a wonderful time exploring Tuscany. Highly recommended!
it was really a well organise trip. Our tour guide Aaron is really nice and experience. Each place you will have sufficient time to walk around. We really love siena
A quiet and quaint town, it feels like there aren't too many tourists. It even has the world's best gelato, which is absolutely delicious. We also bought some local ingredients here, including truffle olive oil and cheese. The whole trip was very relaxing and pleasant, highly recommended.
the guide was great, she organized a very large group and showed caring for everyone. the places we visited were beautiful and picturesque. learning about the pilgrimage path enhances the rich experience we had. this visit is a must on your journey through Tuscany.
beauiful trip. love the drive. lots of free time to walk around. coach is very clean. guide aaron handles both english and spanish, hes always upbeat, maintains a happy mood in the coach.
The one-day tour is very suitable for lazy people. You don't have to worry about transportation and itinerary. You can visit three places at once and enjoy the scenery that is completely different from Florence. The tour guide I met was also very responsible. He counted the number of people at every stop. In the end, when I met tourists from the same group who were late for the meeting in Siena, I quickly called them. Overall, it is quite recommended.
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