Tours and Trip Packages to Siena in October 2025

Traveling to Siena in October 2025? We offer 2 tours, trips and vacation packages to Siena in October 2025. Our Siena in October 2025 tour packages and trips have 63 customer reviews. All the Siena October 2025 tour packages and trips are carried out by hand-picked, qualified local and international Siena tour operators.

2 Trips in Siena during October 2025

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Tuscany Walks & Chianti Wines

of 38 reviews
  • Best price guaranteed
  • No booking fees
One week of great walks , great hospitality and great food .. superb leader in Mark and combined wit ...
  • Tour Type Small Group Tour
  • Activities Trekking and Hiking & Food tours
  • Accommodation Hotel
  • Transport Train
  • Age Range 18-99 yrs
  • Operated in English
days08 From US$ 2,617 US$ 2,245
SavingUS$ 372
You've unlocked exclusive savings:
  • Brochure Price:US$ 2,617
  • Special Deal (14%):- US$ 372
  • Total Price from:US$ 2,245
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Next Departures
  • Oct 11 Only 8 seats left
  • Oct 18 Only 8 seats left
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Via Francigena: Walk from Lucca to Siena

of 1 review
  • Trip customizable
  • Best price guaranteed
8 day trekking and hiking tour through Lucca, Altopascio, San Miniato Alto and 4 other destinations in Italy. Read More
  • Tour Type Private Tour
  • Activities Trekking and Hiking & Walking tours +3 more
  • Accommodation Hotel & Hostel
  • Transport Private Vehicle
  • Age Range 18-99 yrs
  • Operated in English
days08 From US$ 640 View Tour
Next Departures
  • Oct 01
  • Oct 02
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Siena Tour Reviews

5 - Excellent
Based on 63 customer reviews
Autumnal delight
5 - Excellent
  • Anonymous
“A fantastic week of walking in golden hued countryside, sampling local wines and enjoying local food. The group was great, the guide (Mark) top notch, the hotel and staff lovely, the organisation seamless - who could ask for more.”
Tuscany Walking and Wine
5 - Excellent
  • Anonymous
“A really enjoyable and varied week in Tuscany. Three lovely walks through forests and vineyards. Stunning hilltop villages and market towns. Excellent wine tastings and winery visits, each a little different, and we certainly drank a lot of local Chianti. Liz, our guide, was efficient, knowledgeable, capable and so friendly. We had plenty of time to explore the cities of Siena and Florence at our own pace, and on our free day most of us opted for a cookery class at a local restaurant. Enormous fun and the lunch we helped produce, was amazing. The family run farmhouse where we stayed was full of character, and they made us so welcome. The evening meals were generous and based on local produce and served with their own estate wines.”
Right First Time!
5 - Excellent
  • Anonymous
“This was our first actual trip with this tour company and it was all that we hoped for, and more. The balance of walking, wine tasting and culture was spot on! Villa Casalta accommodation was great - simple in a traditional way, owner and Marguerite warmly welcoming and helpful, beautiful swimming pool (used by several of us even though it was end of Sept), entertaining dog (Stella) and cat, with only a slow off-road 20 minute walk to pretty town of Castellina.”
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