TUSCANY · DESTINATION
Most booked first.
Our shortlist of the 6 most-booked chianti classico tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.
Small-group Chianti Classico and Brunello tasting tour from Siena with an organic boutique winery, Montalcino fortress views, and flexible options.
“Our driver, Murad, was exceptionally friendly and informative - he was able to share videos of Palio di Sienna during the drive. Highly recommend!!”
A small-group Chianti Classico tour in Castellina in Chianti: vineyard views, a cellar walkthrough, and a four-wine tasting with food included.
“This was an absolutely wonderful trip! My three friends and I really enjoyed our tour and tour guide, Eduardo. My only complaint is that we were a little rushed at the second stop! We had time to taste the wines and walk around for 10 minutes before having to leave. However, that doesn't really detract…”
Chianti Classico by e-bike from Siena: Brolio Castle views, village rides, wine tasting, and a light lunch in about 5–6 hours.
“Seeing Tuscany on an E Bike was the perfect way to see it. We were two people on a private tour. Our guide Ricardo was very helpful and enjoyable to talk to. Our stop at a winery was a delight and we got to be up close and personal with watching them unload grapes from…”
A small-group Chianti Classico wine-and-food day in Siena with Emanuele, a licensed sommelier, plus three tastings and lunch.
“Professional driver, professional drinker (not during the tour, of course!), and a fantastic tour guide.. that's Ema for you. A licensed sommelier, who is very knowledgeable, personable, funny, and his passion for his country/town was enjoyable to hear & see. He took us to 3 fabulous wineries that we would never have discovered. Nothing but…”
Private 8-hour Siena tour: San Gimignano and Chianti Classico, Monteriggioni walls, wine tastings, WiFi, and flexible stops.
“Maurizio, Cosimo, and Bruno were amazing professionals! We hired We Drive You Tuscany as our on call shuttle services for our wedding and I cannot express how absolutely amazing they were. They were kind, helpful, and always ready with Read more”
Private Siena and Chianti day from Florence with Siena walking, SS222 countryside stops, Falorni tastings, and optional organic farm lunch.
“Enjoyed this tour so much. Alessandro tailored the trip to our preferences. He took us to two boutique farms that produced organic wineries. We ordered wines from both places to be shipped home. Both farms had very high quality wines. Also visited the beautiful city of Siena. Highly recommend this tour.”
