Traveling to Siena in September 2023? We offer 16 tours, trips and vacation packages to Siena in September 2023. Our Siena in September 2023 tour packages and trips have 57 customer reviews. All the Siena September 2023 tour packages and trips are carried out by hand-picked, qualified local and international Siena tour operators.

18 Trips in Siena during September 2023

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Vespa & Chianti Tour from Siena

of 2 reviews
  • Free cancellation
  • Best price guaranteed
This was absolutely the best tour / trip we've ever done. You must do this. The views are amazing. ...
  • Tour Type Small Group Tour
  • Activities Bicycle tours & Farm and plantation visits
  • Accommodation No Accommodation
  • Age Range 18-99 yrs
  • Operated in English, Italian, Spanish
hours7.5 From US$ 139 View Tour
Next Departures
  • Sep 01
  • Sep 02

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 18-99 yrs
  • Operated in English
days08 From US$ 2,049 View Tour
Next Departures
  • Sep 02 Only 1 seat left
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Brunello di Montalcino Wine Tour from Siena

of 1 review
  • Free cancellation
  • Best price guaranteed
This tour can be described in one word - amazing. Great guide and wine tour. Would highly recommend ...
  • Tour Type Small Group Tour
  • Activities Wine tasting tours & Cultural, religious and historic sites
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Spanish
hours5.5 From US$ 97 View Tour
Next Departures
  • Sep 01
  • Sep 03
Add to your Tour Wish List 5% OFFTODAY

Grand Journey of Italy - 11 Days

of 1 review
  • Trip customizable
  • Best price guaranteed
Perfect group tour covering Italy. Well paced with plenty of activities balanced with good free time ...
  • Tour Type Group Tour
  • Activities Art and architecture & Cultural, religious and historic sites +3 more
  • Accommodation Hotel
  • Transport Bus & Coach
  • Age Range 1-99 yrs
  • Operated in English
days11 From US$ 2,730 US$ 2,593
SavingUS$ 137
You've unlocked exclusive savings:
  • Brochure Price:US$ 2,730
  • Special Deal (5%):- US$ 137
  • Total Price from:US$ 2,593
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Next Departures
  • Sep 01
  • Sep 03
Tour with flexible booking policy
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Pienza and Montepulciano Tour from Siena

  • Free cancellation
  • Best price guaranteed
11.5 hour wine tasting trip through Tuscany and Siena. Read More
  • Tour Type Group Tour
  • Activities Wine tasting tours & Art and architecture
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in Chinese, English, Italian, Portuguese, Spanish
hours11.5 From US$ 92 View Tour
Next Departures
  • Sep 02
  • Sep 04
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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 18-99 yrs
  • Operated in English
days08 From US$ 1,190 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
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Guided Walking Tour of Siena with Cathedral

  • Free cancellation
  • Best price guaranteed
2 hour walking trip in Siena. Read More
  • Tour Type Group Tour
  • Activities Walking tours
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Spanish
hours02 From US$ 43 View Tour
Next Departures
  • Sep 01
  • Sep 02
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Chianti & Castle Tour from Siena Small Group

  • Free cancellation
  • Best price guaranteed
5 hour art and architecture trip through Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Art and architecture
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Spanish
hours05 From US$ 92 View Tour
Next Departures
  • Sep 02
  • Sep 05
Add to your Tour Wish List 5% OFFTODAY

Italy City Break - 5 Days

of 1 review
  • Trip customizable
  • Best price guaranteed
This is a well organized tour to see Italy. Our tour guide is knowledgeable and fun. I recommend thi ...
  • Tour Type Group Tour
  • Activities Cultural, religious and historic sites & Local culture +3 more
  • Accommodation Hotel
  • Transport Bus & Coach
  • Age Range 1-99 yrs
  • Operated in English
days05 From US$ 1,060 US$ 1,007
SavingUS$ 53
You've unlocked exclusive savings:
  • Brochure Price:US$ 1,060
  • Special Deal (5%):- US$ 53
  • Total Price from:US$ 1,007
View Tour
Next Departures
  • Sep 02
  • Sep 04
Tour with flexible booking policy
Add to your Tour Wish List 5% OFFTODAY

Discovery of Italy: 8 Days

of 1 review
  • Trip customizable
  • Best price guaranteed
I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences a ...
  • Tour Type Group Tour
  • Activities Cultural, religious and historic sites & City sightseeing +1 more
  • Accommodation Hotel
  • Transport Bus & Coach
  • Age Range 1-99 yrs
  • Operated in English
days08 From US$ 1,800 US$ 1,710
SavingUS$ 90
You've unlocked exclusive savings:
  • Brochure Price:US$ 1,800
  • Special Deal (5%):- US$ 90
  • Total Price from:US$ 1,710
View Tour
Next Departures
  • Sep 01
  • Sep 03
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Cooking Class from Siena

  • Free cancellation
  • Best price guaranteed
4 hour cooking classes tour through Chianti and Siena. Read More
  • Tour Type Group Tour
  • Activities Cooking classes
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Spanish
hours04 From US$ 139 View Tour
Next Departures
  • Sep 01
  • Sep 02
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500 Vintage Tour - Chianti Roads from Siena

  • Free cancellation
  • Best price guaranteed
7.5 hour wine tasting trip through Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Wine tasting tours & Sightseeing Tours
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Spanish
hours7.5 From US$ 162 View Tour
Next Departures
  • Sep 01
  • Sep 02
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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 18-99 yrs
  • Operated in English
days09 From US$ 1,950 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
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Via Francigena: Southern Tuscany from Siena

of 2 reviews
  • Best price guaranteed
  • No booking fees
As a travel writer who has had too much of being met and taken everywhere I go, the chance to
  • Tour Type Private Tour
  • Activities Hiking
  • Accommodation Hotel
  • Transport Train
  • Age Range 18-99 yrs
  • Operated in English
days08 From US$ 1,150 View Tour
Next Departures
  • Sep 01 10+ seats left
  • Sep 02 10+ seats left
Showing 1 - 14 of 18 results
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    Roberta Leverone
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  • Stefania Grillo
    Stefania Grillo
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    Veronica Maggi
    Travel Expert in Italy & Switzerland
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Siena Tour Reviews

5 - Excellent
Based on 57 customer reviews
Best decision ever
5 - Excellent
  • Anonymous
“The trips organized by the tour operator were recommended to me, and as someone who knows little about wine but loves to drink it I was keen on this trip. I also fancied some exercise and activities thrown in. I was slightly dubious about going alone but soon realised when I got there that the tour operator caters for people like me. I would say the trip is scaled correctly in terms of activity level, I particularly enjoyed the panzano and San gimignano walks. There's also loads to do on your free day, I rented a vintage fiat from castellina, some of the group went riding and others cooking so plenty of options. Couldn't recommend this trip enough.”
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.”
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.”