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  • Explore Siena
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  • Outside Siena

Siena Cathedral

Palazzo Pubblico

Tower of Mangia, Siena

Brolio Castle

Cripta del Duomo di Siena

Monte dei Paschi di Siena

Santa Maria della Scala

Piccolomini Library

Piazza del Duomo, Siena

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Museo Civico, Siena

Piazza del Campo

Day trips

Landmarks & monuments

UNESCO sites

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Florence tours

Pisa tours

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Montepulciano tours

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Nearby sights

Florence Duomo ComplexAttraction in Florence, Italy

Ponte VecchioAttraction in Florence, Italy

Piazza della SignoriaAttraction in Florence, Italy

Uffizi GalleryAttraction in Florence, Italy

Accademia GalleryAttraction in Florence, Italy

Porta del ParadisoAttraction in Florence, Italy

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Cooking classes

Pasta tasting & cooking classes

Olive oil tours & tastings

Bike tours

Balloon tours

Horse riding

Rail tours

Scooters & motorcycles

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Hiking

Vespa tours & rentals

Explore more things to do in Siena

Sightseeing

Food & drinks

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Explore more things to do in Siena

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Explore more things to do in Siena

From Siena: Chianti and San Gimignano Sunset Tour

Top rated
4.8 out of 5 stars
4.8
69 reviews
Activity provider:
Tuscan Escapes by Papilio
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From Siena: Chianti and San Gimignano Sunset Tour
Top rated
4.8 out of 5 stars
4.8
69 reviews

Discover Chianti and the town of San Gimignano on a group tour from Siena. Taste the wines and food of Tuscany at a Chianti winery and farm and enjoy a typical local dinner with wine.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 9 hours
Check availability to see starting times
Live tour guide
English
Small group
Limited to 8 participants

Highlighted reviews from other travelers

5
5 out of 5 stars
K
Karen – United States

Our group thoroughly enjoyed our trip to the winery in Chianti, our hours spent in San Gimignano, and our delicious dinner at the farm. Our guide, Keko, was a delight. He was extremely knowledgeable and shared a great deal of information with us while we traveled to each destination comfortably in the air-conditioned van. We would absolutely recommend this tour and highly suggest requesting Keko!

5
5 out of 5 stars
S
Stephanie – Canada

Guillermo was an absolutely fantastic guide! His knowledge of the history was impressive, and he brought each story to life in a way that made the experience truly unforgettable. He was also incredibly attentive to all of us, ensuring everyone felt comfortable and engaged throughout the tour. I can't recommend Guillermo highly enough—if you're looking for an insightful and enjoyable experience, he's the guide to ask for!

Select participants and date

Participants

Highlights

  • Taste the wines of Chianti and the Chianti Classico wine region
  • Enjoy a dinner of typical Tuscan produce as you watch the sunset
  • Explore the medieval town and towers of San Gimignano
  • Go to the medieval fortress of Monteriggioni

Full description

Explore the Chianti wine region and the hilltop town of San Gimignano on a sightseeing and wine-tasting tour from Siena. Travel in a small group and enjoy comfortable transfers by air-conditioned vehicle.

Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands: neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind.
Head to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of local Chianti wines and olive oil. Explore the medieval fortress of Monteriggioni and marvel at its intact ring of walls and turrets.

Travel to the village of San Gimignano to enjoy the charming streets and laneways as the sun begins to set and daytime crowds have departed. Admire the medieval towers at a leisurely pace, and explore the many streets and squares. Visit the boutique stores of local crafts and products.

Enjoy a typical Tuscan dinner at a local farm in the countryside. Taste the white wine of San Gimignano, the Vernaccia, or have some local Chianti red wine. Weather permitting, dinner will be served outdoors. Return to Siena after dinner.

Includes

  • Transportation by comfortable, air-conditioned vehicle
  • English-speaking expert guide
  • Chianti winery tour and wine tasting
  • Tuscan dinner with wine at farm
  • Hotel pick-up and drop-off
  • Tips and gratuities

Meeting point

Meet your guide under the large tree at San Domenico Basilica, Siena

Open in Google Maps

Important information

What to bring

  • Comfortable shoes

From $209 per person

Reserve now & pay later to book your spot and pay nothing today
Reserve now & pay later to book your spot and pay nothing today

Customer reviews

Overall rating

4.8 /5
4.8 out of 5 stars

based on 69 reviews

Review summary

  • Guide
    4.6/5
  • Transportation
    4.8/5
  • Value for money
    4.8/5

Customer photos

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5
5 out of 5 stars
K
Karen – United StatesJuly 6, 2025 – Verified booking
Our group thoroughly enjoyed our trip to the winery in Chianti, our hours spent in San Gimignano, and our delicious dinner at the farm. Our guide, Keko, was a delight. He was extremely knowledgeable and shared a great deal of information with us while we traveled to each destination comfortably in the air-conditioned van. We would absolutely recommend this tour and highly suggest requesting Keko!
5
5 out of 5 stars
S
Stephanie – CanadaSeptember 3, 2024 – Verified booking
Guillermo was an absolutely fantastic guide! His knowledge of the history was impressive, and he brought each story to life in a way that made the experience truly unforgettable. He was also incredibly attentive to all of us, ensuring everyone felt comfortable and engaged throughout the tour. I can't recommend Guillermo highly enough—if you're looking for an insightful and enjoyable experience, he's the guide to ask for!
5
5 out of 5 stars
R
Robynann – AustraliaJune 19, 2024 – Verified booking
This tour gave me a wonderful slice of Tuscany- the drive through the countryside, the 2 medieval towns different in style and feel and then the most marvellous dinner with a charming host/owner! Simply the best I felt very privileged to be there

Product ID: 47303

Activity provider:
Tuscan Escapes by Papilio
  • Italy
  • Tuscany
  • Things to do in Siena
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Top Attractions in Siena

  • 1Siena Cathedral
  • 2Brolio Castle
  • 3Palazzo Pubblico
  • 4Tower of Mangia, Siena
  • 5Oratory of San Bernardino
  • 6Santa Maria della Scala
  • 7Cripta del Duomo di Siena
  • 8Facciatone
  • 9Piazza del Campo
  • 10La Lastra Winery
  • 11Winery San Giorgio a Lapi
  • 12Basilica Cateriniana San Domenico
  • 13Baptistery of St John
  • 14Meleto Castle
  • 15Santuario di Santa Caterina
  • 16Museo Civico, Siena
  • 17Opera della Metropolitana
  • 18Piccolomini Library
  • 19Fortezza Medicea
  • 20Monte dei Paschi di Siena

Experiences in Siena

  • 1Siena Wine tasting & winery tours
  • 2Siena Walking tours
  • 3Siena Day trips
  • 4Siena Transfers
  • 5Siena Driving experiences
  • 6Siena Cooking classes
  • 7Siena Family-friendly activities
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