Tuscany Day Trip From Florence With Chianti, Siena and San Gimignano

1507

9 h

All Day

14 max

Walks Florence Tuscany from Florence 0207

Walks Florence Tuscany from Florence 0001

Walks Florence Tuscany from Florence 0007

Walks Florence Tuscany from Florence 0013

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Overview

When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and wander the storybook streets of the UNESCO-listed village San Gimignano. Group size is limited to 14 for a more personalized experience.

Travel to three stunning cities in Tuscany.
Walk through Siena and Piazza del Campo.
Visit Chanti for a seasonal lunch with wine.
Indulge in a wine tasting & tour a Chianti vineyard.
Stop in San Gimignano with free time to shop and explore.

Tuscany Day Trip from Florence Itinerary

Your day starts in Central Florence where you’ll meet your small group of no more than 14 people and an expert tour guide. Then you’ll hop into private transportation and be spirited out of the city and over to Siena. On the way out of the city, we'll pass the best panoramic viewpoint of Florence and stop to take a few pictures.

A little over an hour drive away, Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared bombing in World War II, ...

Price

$205

Free Cancellation

A Sustainability Message from Walks Tours

Walks Tours is dedicated to exploring the world’s most iconic attractions responsibly. Since 2009, we've guided over 3 million travelers, in small groups, to minimize impact and create genuine connection with each destination. By working with the best local guides and designing special access to crowded sites, we ensure a high-quality experience that supports sustainable tourism and preserves remarkable cultural heritage.

from $ 205

Free Cancellation

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Meeting Point

We meet by the Carousel in Piazza della Repubblica. Piazza della Repubblica is one of the main squares in the historical centre of Florence. In the middle of the square you will see a Carousel. We meet just by the Carousel, next to the ticket booth.

Total Customer Reviews: 1507

Verified Ratings

4.7 /5

based on 1507 Devour customer ratings

Rating Summary by Category

Guide
4.7/5
Food & Drink
4.8/5
Guest Support

        4.7/5
      

Latest Reviews

Excellent

We had an amazing day trip from Florence visiting Siena, San Gimignano and a family owned winery in Chianti. There were 12 in our group and our guide, Annette, was wonderful. She was able to answer all our groups questions and knew the history and area very well. We departed Florence at an easy to find location, with good communication by Walks, in 2 smaller Mercedes 8 passenger vans/buses. Annette communicated with the group by provided easy to wear and hear earpieces even while in the vans. She rotated between the two vans so we could ask questions. The sites we visited were great and she gave us an easy walking tour overview of each town and then gave us some free time in each with suggestions of places to go. The Siena cathedral was not included in the trip but she was able to help us purchase tickets quickly and guide us to the entrance. She also took those in the group that wanted to go to the top of the city walls in San Gimignano. The highlight was that they skip the large wineries and take their tours to a local family owned winery. We really enjoyed the short tour and learning more about the Chianti winery we visited. We had lunch there and tasted 5 wines. It was a great experience!! Walks/Devour are 2 for 2 with us and we even booked another tour with them because we enjoyed the others so much!

Verified · Laura · Mar 29, 2025 · USA · Female · 45 to 54 years

Great

Guillia was a terrific guide. Her knowledge of the area was excellent. The winery lunch was great! The

Verified · Hilary · Mar 22, 2025 · USA · Female · 75 or older years

Excellent

Greta was amazing. We loved the bits of history and the free time to explore. Even our teens enjoyed the day. Breathtaking and hospitality was exceptional!

Verified · Margaret · Dec 28, 2024 · USA · Male · 45 to 54 years

Great

Spectacular day! Highly recommend! *My only warning to people is that there is a lot of walking, often up steep inclines and/or steps. It would not be appropriate for someone who was not up for these endeavors.

Verified · Josh · Dec 27, 2024 · USA · Male · 55 to 64 years

Excellent

This was a fantastic tour, our best so far. Both adults and the 11-year old in our party loved it. The pace of the day was great with a perfect mix of guided tour and free time to explore Siena and San Gimignano. Our guide, Connie, was so knowledgeable, helpful, and organized. And the lunch and wine tasting were among our best meals — they accommodated both vegetarian and gluten-free requests deliciously. Our favorite day so far in Italy! Grazie mille!

Verified · Monica · Dec 27, 2024 · USA · Female · 35 to 44 years

Know Before You Book

Am I able to participate in this tour if I have allergies or dietary restrictions?

Those with dietary restrictions need to contact us before joining the tour so we can arrange your included lunch.

Are young children able to participate in this tour?

Yes, however, we kindly request that you contact us if you are traveling with a small child. We need to confirm space on the vehicle for them.

Is this tour accessible to guests with mobility impairments?

Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments, or for wheelchairs or strollers. Please contact the Guest Experience team at info@takewalks.com to make alternative arrangements.