TUSCANY · DESTINATION
Most booked first.
Our shortlist of the 8 most-booked tuscan countryside tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.
5-hour Chianti tour from Siena with a small minivan, Castellina and Monteriggioni, plus two winery tastings with snacks and views.
“It was excellent and well-timed. Great value for the money!”
Full-day Chianti and Val d’Orcia wine tour from Siena with two tastings, olive oil, and stops in Pienza and Montepulciano.
“At september 14 morning the bus pick up us (was late like 30min, they arrived from Florance, i guess the traffic was crazy) Had a wonderful day with our tour guides- she was soooo informative and spoke 3languages- first stip Montalcino. Drinking wine, had a little.... little! snack. Than heading to Pienza. Try some pecorino…”
Horseback through Siena’s countryside with calm horses, guided stories, and optional river picnic or winery tasting. Small group.
“An amazing day out, definitely worth the money. Beautiful countryside and the guide was very accommodating. You don’t need any previous experience to ride. I would highly recommend to see the Tuscan countryside and ride through vineyards”
Small-group Chianti wine tour from Siena with two tastings, 7 wines, olive oil and snacks, plus Castellina and Monteriggioni.
“It was a wonderful opportunity to see the Tuscany countryside and taste wines of the region. Velasca is an informative guide who made the trip interesting and fun and Antonio drove us safely throughout our travels. Besides visiting two wineries we visited villages also. It was a very beautiful way to see more of Tuscany!”
Horseback through Siena’s countryside with calm horses, small groups, vineyard and olive grove views, and optional Tuscan food stops.
“Due to the heavy rain, and the fact that I could not postpone the activity to the next day, Melissa, the organizer, offered me to do another activity i.e cooking class, instead for no extra-fee, which I accepted. She has been so careful and helpful to me, regarding all the aspects of the activity: the…”
Ride an original automatic Vespa through Chianti hills from Siena or Badesse, visit Castellina, then taste wines at a Tuscan winery.
“We had the best day exploring the Chianti wine region! We were the only two people on the tour so it felt very personalised. We stopped at cute villages and the tour guide took lots of photos of us on the Vespa. The lunch was LARGE! Nothing light about it. Would highly recommend if you…”
Drive a vintage Fiat 500 from Siena through Chianti hills to Monteriggioni, then enjoy a winery lunch with wine tasting.
“Was able to spend the wonderful day with my son, on his birthday, and his family. My wife and I were trying to find a surprise that he would never figure out. It worked.”
Small-group horseback riding from near Siena on calm horses, walk-only for beginners, with big views over Crete Senesi and Val d’Arbia.
“The horses are well cared for, and the guides are wonderful! The tour loops around the local valley, so it's a long and beautiful route.”
