3 Best Siena Tours

From Siena: Chianti and Castles Tour with Wine Tastings

/ June 19, 2026

1.From Siena: Chianti and Castles Tour with Wine Tastings

Half-day Chianti from Siena with a small minivan, two winery tastings, and hilltop villages like Castellina and Monteriggioni.

Most Popular★ 4.6

“The viewing points that Chico showed us were great, especially with the autumn colour to the trees and they showed off the Chianti area superbly. The tour of Lornano winery and the tasting were delightful, as were the wines and snacks at Poggio Al Laghi. Our hosts were brilliant.”

631 reviews5 hoursFrom $100by My Luxury Drive

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Siena, Tour Reviews

Hidden Castles & Chianti Wine Experience– Small Group

/ August 12, 2026

2.Hidden Castles & Chianti Wine Experience– Small Group

Small-group Chianti wine tour from Siena: 2 wineries, 7 tastings, olive oil bites, and Monteriggioni walls in 5 hours.

★ 4.5

“Both wineries had excellent wine tastings with knowledgeable and friendly hosts. Our guide did a great job describing the Chianti region and history. The town and castle were highlights too.”

172 reviews5 hours (approx.)From $59.13by myTour in Italy

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Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

/ August 28, 2026

3.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Brunello in a medieval Montalcino castle: vineyard walk, sommelier tasting of three wines, and a 3-course Tuscan lunch.

★ 4.5

“Great little tour of the property followed by a great lunch with tastings to match. We very much enjoyed the experience and the company of those we shared our tour with.”

92 reviews1 hour 30 minutes (approx.)From $71.23by Hidden Experiences

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