TUSCANY · DESTINATION
Most booked first.
Our shortlist of the 5 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 guide Morad was really friendly and informative, had a short stop at Monteriggioni first to walk round the castle and then onto the Lornarno winery for the tasting. Lovely tour and enjoyed their wines and snacks”
A small-group Chianti Classico tour in Castellina in Chianti: vineyard views, a cellar walkthrough, and a four-wine tasting with food included.
“do not book if you only have one or two people in your party!! The website says it’s okay and they let you book and take your money but i was messaged saying it’s not possible the day of. over 5 hours before the tour i said i could have at least two more people…”
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.
“This was hands down one of the best days of our entire six week European trip. Our driver was a genuine local, passionate about his area. The villages fantastic, and the lunch at a family winery simply stunning. Highly recommended in every respect.”
