15 Best Chianti Wine Tours

“We went on this day trip during our honeymoon in October 2025. This excursion was an outstanding experience thanks to our tour guide, Giancarlo. He was engaging, informative, funny, and knowledgeable. Siena, San Gimignano, Pisa, and lunch at the winery were beautiful. It is a…”

“An absolutely fantastic experience and highly recommend it. Our chef Andrea shared great knowledge and made the experience fun. Would definitely do it again”

“Anna was the perfect guide. The two wineries she took us to was expertly selected with one showing history and the whole process while the other was more homely and interactive. A definite recommend.”

“Everything was wonderful! The guide was great and the transportation exceeded my expectations. Generous samplings of wine and food.”

“Our chef instructor, Narghess, was great. She was funny, friendly and very patient. Her English was exceptional and she knew many humorous American idioms. She kept us in stitches. She also was very generous with the libations during our pasta prep. After we made two…”

“A great way to see the highlights of Tuscany if you are staying in Florence! We chose to do the guided Siena tour and lunch at the vineyard and it was well worth it. Siena and San Gimignano are real gems and the lunch at…”

“This experience was exceptional in large part thanks to our tour guide Ado. The vineyards visited were truly stunning and looked out of movie, the wine was delicious and the dinner even more so! The entire group bonded over the food and how much fun…”

“Well worth the money. Alice, the guide was a really fun person and the we went to great places. A truly enjoyable experience.Strongly recommended.”

“Great trip. Lots of walking. I had 7 miles logged on the smart watch. It was a long day. Unfortunately we got to San Gimignano by 9 . Most of the top sites didn’t open until 10;30 or 11. We left at 10:45 for the…”

“This was an extremely interesting tours. Our guide and driver was exceptional attentive and helpful. Would highly recommend and want to do this tour again when I'm next in Tuscany. The wine, olive oil and balsamic we tasted as extremely good too!”

“Amazing trip! Super easy pickup spot to get to from Florence, and the guide was so informative and fun. The vineyards were absolutely stunning and I can’t recommend it enough!”

“This tour was a well organised and jam packed day providing the opportunity to visit Pisa, Siena and the mediaeval town of San Gemignano. Guide Hilary was excellent- effortlessly switching between English and Spanish all day, and providing excellent information, advice and information. Definitely recommend…”

“Amazing cooking class with Tonya. Excellent step by step and so much fun!! Tiramisu was amazing and had fun learning how to make pasta from scratch.”

“Amazing experience!! Tour was amazing and being in Tuscany tasting wines, a dream come through! The tour was amazing!! Love Chianti!”

“The guides did an expert job at explaining how to ride a Vespa and keep safe on the road. We all did a practice loop in the courtyard before going out onto the road. It was such a fabulous day riding through the beautiful Tuscan…”