Florence · SIENA DAY TRIPS
Siena is an hour and a quarter south and the Campo is worth the drive on its own. These 15 compare the trips that stop only there with the ones that add San Gimignano and a winery, priced and timed.
Review of a full-day Tuscany tour from Florence, visiting Siena, San Gimignano, Pisa, and a Chianti winery lunch.
“We had so much fun! Alex and Sergio were amazing. The fun facts throughout the tour from Alex were informative. I fell in love with Italy even more than I already have. Definitely recommend this tour.”
See Pisa, Siena, and San Gimignano in one long Tuscan day, with a Chianti winery lunch, wine tasting, and optional English tours.
“This trip is a great value. So much so that I was concerned it couldn’t possible meet the expectation. However, the day was fantastic. Our guide Val was so informative and funny and helpful! The bus was so clean and so comfortable. You can leave your belongings on the bus, so bringing an umbrella or extra layers just in case weather changes was perfectly fine. We did not know ahead of time, but there is no eating or drinking on the bus and we did have plans for that, however, not a big deal. Each spot was so fun and so informative, and overall the day covered so much ground.…”
See Pisa, San Gimignano, Siena, and Chianti in one long Tuscany day, with optional lunch, wine tasting, Siena guide, and Leaning Tower tickets.
“Thank you Barbara…very knowledgeable,with soft & gentle voice and very kind.To Franco our driver,thank you for safe journey..”
See Siena, San Gimignano, Pisa, and a Tuscan winery in one long day from Florence, with coach travel, lunch, and wine pairing options.
“Fabulous tour with guide Simone and Roberto. This was the best part of our trip. Thankful to see Pisa, Siena and San Gemignano was spectacular and the wine tasting with luncheon was very memorable.”
See Siena, San Gimignano, Pisa, and Chianti on a full-day Florence tour with a winery lunch, wine tasting, and expert guides.
“It was great and perfect. Tour guide was super good, fun and friendly. Making everyone feel welcome and the tour enjoyable! 1000% to join this tour!”
Explore San Gimignano, Siena, Monteriggioni, and Chianti from Florence with a winery lunch, three wines, and free time.
“Guide Alejandra was knowledgeable and give us the information in English and Spanish. The three medieval towns were charming and worth visiting as well as the family owned winery and olive oil producers. The Tuscan meal was simple (typical) and good. The family vineyard owners were charming and friendly so we had a lovely time. Their gift shop was good and we were lucky to have just been able to buy the new production of extra virgin olive oils for 2025 which were available just this week!!! Their dessert wine was delicious so we bought a bottle. All in all it was a fun experience. We did have an issue…”
See Pisa, San Gimignano, Chianti, and Siena in one long Tuscan day, with bus transport, optional lunch, wine tasting, and a Siena guide.
“Our tour guide Marta was perfect. She explains everything with details and we really enjoy the experience. The day trip is worth it. Also, really thanks to Silvio, the driver! 🤍”
See Siena, Chianti, and San Gimignano in one full day from Florence, with five wine tastings, a Tuscan lunch, and free time in medieval towns.
“We had an incredible adventure through Chianti and surrounding towns. Marco was an excellent guide who is very knowledgeable of Tuscan and Italian history. San Gimingnano was the highlight filled with delicious treats and sights of the picturesque rolling hills.”
See Siena, San Gimignano, Monteriggioni, and a Chianti estate in one well-organized day trip from Florence for $46.
“The tour was absolutely amazing! Loved every minute of it. Federico and Patroclaw (sorry if that’s not the correct spelling) were phenomenal. The only thing that bummed me out was that it got dark too fast in San Gimignano, but that’s no one’s fault, just that time of year. Highly recommend!”
Review of a full-day Tuscany tour from Florence to Siena, San Gimignano, Monteriggioni, and a Chianti wine estate.
“Beautiful countryside and interesting places to see. The reason rating not higher was it combined 3 languages on same tour Made it complicated. Winery was a commercial operation. Hoped the wine tasting to be overlooking the Tuscan hills”
Review of Florence’s Tuscany day trip to San Gimignano, Siena, Monteriggioni, and a Chianti winery lunch with three wine tastings.
“Fantastic Day Trip! We had a wonderful experience on this tour. Guides, Marta and Stella, were incredibly friendly, knowledgeable, and organised. They made sure everyone was comfortable and informed throughout the day. Our driver, Elis, was professional and smooth—navigating the scenic Tuscan roads with ease. This tour is a great value for the price and perfect for travelers looking for a stress-free way to visit iconic locations in Tuscany. Highly recommend!”
See Pisa, Siena, San Gimignano, and Chianti in one long, food-filled day from Florence, with a Siena guide, cathedral visit, lunch, and wine tasting.
“Our tour guide , Fabiana, was absolutely amazing. I travel with two elderly parents and she was more than accomodating and helped us stay with the group. The views and different tours were amazing and fun.”
Explore Siena, San Gimignano, and a Tuscan winery on a 10-hour small-group day trip from Florence, with lunch, wine, and free time.
“Even though the other guests did not turn up Francesco our driver/guide and Lorenzo our guide for Siena happily treated us to a private tour full of fun and key facts about the locations we visited and the people living there; a thoroughly pleasant experience.”
See San Gimignano and Siena from Florence with comfortable transport, free time, local tips, and a multilingual tour leader for $71.
“The tour was organized well and Sara, our guide and Giovanni, our driver gave a good day trip to San Gimignano and Siena. Sara provided information of each location before arrival and a WhatsApp message containing the audioguide, places to visit and map of the meeting point, which I appreciate since Siena is big and one can get lost or walk too far. I especially loved San Gimignano and the artisan work there and appreciated the time allocated in both locations.”
See Pisa, San Gimignano, and Siena from Florence in one long Tuscan day, with coach transport, winery lunch, wine tasting, and Siena Cathedral.
“The tour was amazing! The tour guides Marco, Raffi and Michelle were friendly, knowledgeable and helpful. They went out of their way to make sure everyone was enjoying themselves. They even went over and able their job to help us after my husband dislocated his shoulder in Pisa. They were compassionate patient and helpful. Thank you so much for caring and helping us get to the hospital!”
Pick a gallery, a kitchen or a road south.
