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Traveling to Siena in Fall 2022/2023? We offer 21 tours, trips and vacation packages to Siena in Fall 2022/2023. Our Siena in Fall 2022/2023 tour packages and trips have 54 customer reviews. All the Siena Fall 2022/2023 tour packages and trips are carried out by hand-picked, qualified local and international Siena tour operators.

21 Trips in Siena during Fall 2022/2023

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Half-Day Guided Hike to Monteriggioni from Siena

of 1 review
  • Free cancellation
  • Trip customizable
4 hour countryside and village visits trip through Siena and Monteriggioni. Read More
  • Tour Type Small Group Tour
  • Activities Countryside and village visits & Hiking +2 more
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours04 From US$ 46 View Tour
Next Departures
  • Sep 01
  • Sep 05
Tour with flexible booking policy

Chianti Walking & Wine

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 & Food tours +1 more
  • Accommodation Villa
  • Age Range 18+ years old
days08 From US$ 1,999 View Tour
Next Departures
  • Sep 03 Only 2 seats left
  • Sep 10 Only 1 seat left
Tour with flexible booking policy
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Small Group Brunello Wine Tour from Siena

of 1 review
  • Free cancellation
  • Trip customizable
We had the most fantastic trip on our brunello wine tour. It was the best tour on our whole Italian
  • Tour Type Small Group Tour
  • Activities Wine tasting tours & Farm and plantation visits
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours09 From US$ 153 View Tour
Next Departures
  • Sep 01
  • Sep 02
Tour with flexible booking policy
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Small Group Pienza & Montepulciano Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour cultural, religious and historic sites tour in Siena. Read More
  • Tour Type Small Group Tour
  • Activities Cultural, religious and historic sites & Farm and plantation visits +1 more
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours08 From US$ 143 View Tour
Next Departures
  • Sep 01
  • Sep 05
Tour with flexible booking policy
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Small Group San Gimignano & Volterra Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour cultural, religious and historic sites trip through Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Cultural, religious and historic sites & Art and architecture +3 more
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours08 From US$ 143 View Tour
Next Departures
  • Sep 02
  • Sep 06
Tour with flexible booking policy
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Small Group Chianti & San Gimignano Sunset Wine Tour

  • Free cancellation
  • Trip customizable
On this day trip you will visit Chianti, Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Beer and drinks tasting
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours08 From US$ 153 View Tour
Next Departures
  • Sep 03
  • Sep 07
Tour with flexible booking policy
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Via Francigena: Lucca to Siena

of 1 review
  • Best price guaranteed
  • No booking fees
This was an absolutely wonderful trip. The organisation was excellent, accommodation much better tha ...
  • Tour Type Private Tour
  • Activities Hiking
  • Accommodation Hotel
  • Transport Train
  • Age Range 18+ years old
days08 From US$ 1,190 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
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Small Group Chianti and Castles Wine Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour farm and plantation visits trip through Chianti and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Farm and plantation visits & Wine tasting tours
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 5+ years old
hours08 From US$ 153 View Tour
Next Departures
  • Sep 01
  • Sep 05
Tour with flexible booking policy
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E-Bike Chianti Tour from Siena with Winery Lunch

  • Free cancellation
  • Trip customizable
7 hour bicycle trip in Siena. Read More
  • Tour Type Small Group Tour
  • Activities Bicycle tours
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 13+ years old
hours07 From US$ 153 View Tour
Next Departures
  • Sep 02
  • Sep 06
Tour with flexible booking policy
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Chianti & Castle Tour from Siena Small Group

  • Free cancellation
  • Best price guaranteed
5 hour art and architecture tour through Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Art and architecture
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 1+ years old
hours05 From US$ 71 View Tour
Next Departures
  • Sep 01
  • Sep 03

St Francis Way: Chiusi to Città di Castello

of 1 review
  • Best price guaranteed
  • No booking fees
The Full St Francis Way trip with this tour operator was yet another fabulous experience for me. Eve ...
  • Tour Type Private Tour
  • Activities Hiking
  • Accommodation Hotel
  • Age Range 18+ years old
days07 From US$ 990 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
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Small Group Siena City & Duomo Walking Tour

  • Free cancellation
  • Trip customizable
2 hour walking tour in Siena. Read More
  • Tour Type Group Tour
  • Activities Walking tours
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 2+ years old
hours02 From US$ 36 View Tour
Next Departures
  • Sep 01
  • Sep 02
Tour with flexible booking policy
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Cooking Class from Siena

  • Free cancellation
  • Best price guaranteed
4 hour cooking classes trip through Chianti and Siena. Read More
  • Tour Type Group Tour
  • Activities Cooking classes
  • Accommodation No Accommodation
  • Accommodation No Accommodation
  • Age Range 1+ years old
hours04 From US$ 101 View Tour
Next Departures
  • Sep 01
  • Sep 03
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Cycle the Via Francigena - Parma to Siena

  • Best price guaranteed
  • No booking fees
9 day bicycle trip through Parma, Aulla, Massa and 4 other destinations in Italy. Read More
  • Tour Type Private Tour
  • Activities Bicycle tours
  • Accommodation Hotel
  • Age Range 18+ years old
days09 From US$ 2,060 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
Showing 1 - 14 of 21 results
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    Danilo Catania Travel Expert in Italy
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Siena Tour Reviews

5 - Excellent
Based on 54 customer reviews
A perfect mix of walking, wine tasting and sight-seeing
4 - Very Good
  • Anonymous
“This was my 10th trip with this tour operator in 4 years so I am already a fan and it almost provided us with what we'd hoped for. There was a good balance of walking, wine tasting and sight-seeing. The days spent in Florence, Siena and San Gimignano were not at all rushed and we had ample time to do all that we planned. It was also great to be driven in by Simon our wonderful guide. It meant that we spent very little time travelling. Villa Casalta accommodation was simple in a traditional way and our room was beautiful and very clean. We were given a very warm greeting from Roberta on our arrival and she waved us off on our departure however for the rest of the week we hardly saw her. The swimming pool was lovely to sit around but very cold to swim in during October although I did mange it one afternoon. The location is lovely with a pleasant 20 minute walk to pretty town of Castellina along a gravel road.”
Chianti Wine & Walking
4 - Very Good
  • Anonymous
“A good balance of walking in the countryside with visits to towns & cities for that cultural fix. The wine tasting was something I would not usually have done but I learnt from it & found it enjoyable”
Chianti Wine and Walking
4 - Very Good
  • Anonymous
“Everything was excellent apart from the dinners in the hotel we stayed; these were lacking. Served warm rather than hot and unimaginative considering the rich food traditions of Italy. Breakfast was ok but again lacked choice and variety. Warmth of welcome was great but you cannot eat that! Room ok and bed good and firm.”