From Siena: Chianti and Castles Tour with Wine Tastings
1.From Siena: Chianti and Castles Tour with Wine Tastings
5-hour Chianti tour from Siena with a small minivan, Castellina and Monteriggioni, plus two winery tastings with snacks and views.
Tuscan Countryside Tours
TUSCANY · DESTINATION
8 Best Tuscan Countryside Tours In Siena
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.
8 Best Tuscan Countryside Tours In Siena
From Siena: Tuscany Hills Wine Tour
2.From Siena: Tuscany Hills Wine Tour
Full-day Chianti and Val d’Orcia wine tour from Siena with two tastings, olive oil, and stops in Pienza and Montepulciano.
“The mixture of two winery visits and tastings, along with two beautiful towns and the scenery.”
Siena: Horseback Riding Tour in the Tuscany Countryside
3.Siena: Horseback Riding Tour in the Tuscany Countryside
Horseback through Siena’s countryside with calm horses, guided stories, and optional river picnic or winery tasting. Small group.
“There was a taxi strike at the train station, and they were kind enough to pick us up from the train station so we could make the ride in time. The horses are great, guide was amazing. I would definitely recommend this ride for beginners and anyone looking for a relaxing trail ride.”
Hidden Castles & Chianti Wine Experience– Small Group
4.Hidden Castles & Chianti Wine Experience– Small Group
Small-group Chianti wine tour from Siena with two tastings, 7 wines, olive oil and snacks, plus Castellina and Monteriggioni.
“Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in…”
Siena: Horseback Adventure in the Tuscan Countryside
5.Siena: Horseback Adventure in the Tuscan Countryside
Horseback through Siena’s countryside with calm horses, small groups, vineyard and olive grove views, and optional Tuscan food stops.
“This was so much fun!!! Thank you to Melissa for a wonderful horseback riding experience through the vineyard! Her horses were very calm! After a horse ride we went back to their home for a beautiful home cooked meal! It was so fun to talk to Melissa and her father, thank you for the great…”
From Siena/Badesse: Vespa & Chianti Tour in the Tuscan Hills
6.From Siena/Badesse: Vespa & Chianti Tour in the Tuscan Hills
Ride an original automatic Vespa through Chianti hills from Siena or Badesse, visit Castellina, then taste wines at a Tuscan winery.
“We loved our tour! It ended up just being us, our guide, and one other couple. We’d never ridden vespas before but my husband picked it up really quickly. Our guide was great too. He gave us a small amount of history about each hill town we stopped in and then let us explore on…”
Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
7.Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
Drive a vintage Fiat 500 from Siena through Chianti hills to Monteriggioni, then enjoy a winery lunch with wine tasting.
“Of course, 1960s Fiat makes for an interesting challenge…and yes you can smell gas, but we LOVED this experience! The guide and other guests were so much fun. We bonded over laughs and poking fun at some lackluster driving moments, but this made for an experience we’ll never forget! The scenery, towns and wineries were…”
Horsebackriding – explore Tuscan nature
8.Horsebackriding – explore Tuscan nature
Small-group horseback riding from near Siena on calm horses, walk-only for beginners, with big views over Crete Senesi and Val d’Arbia.
“Very well maintained stables, lovely owner, well groomed horses and great riding experience. The views were spectacular. Can cater for all levels.”