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Tuscany with Chianti, Siena, San Gimignano from Florence

  • Travel via comfortable, air-conditioned vehicles from Florence
  • A small group tour makes for a personal way to see the sights
  • Enjoy a traditional Tuscan lunch and wine pairings at a local vineyard
Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
From US$190.34
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  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
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Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano

Exploring the Tuscan countryside is a must when you visit Florence, but arranging your own transit and itinerary can be tricky. This full-day, small-group tour makes it simple to see the highlights of the area. Air-conditioned vehicles whisk you from the heart of Florence straight to Siena, the Chianti wine region, and San Gimignano. You’ll explore the Siena Cathedral, enjoy a traditional lunch and wine tastings, and much more.

What to Expect

This full-day tour begins in a conveniently located meeting point in the center of Florence. Climb aboard your air-conditioned vehicle and make your way to the Tuscan countryside. Before leaving city limits, you’ll pause at the Piazzale Michelangelo to take in the views overlooking Florence.

Your first stop in Tuscany is the medieval town of Siena, a UNESCO World Heritage Site known for its beautifully preserved architecture—with just a small group for company, you’ll enjoy a personal way to discover. Learn about the Palio horse race that’s held here twice every year, and then visit the opulently decorated Siena Cathedral.

Next, you’ll climb back aboard your vehicle and continue to the rolling hills of the Chianti wine region. Stop at a family-owned winery and farm to go for a tour of the vineyards and cellar, learn about the winemaking process, and then settle in for a freshly cooked Tuscan lunch (with glasses of wine to go with).

Once your appetite is sated, you’ll head to your final stop: the medieval town of San Gimignano, known for its soaring towers and also a UNESCO World Heritage Site. Explore at your leisure before returning back to your vehicle and continuing to the Piazza della Repubblica in Florence, where the tour ends.

Write a ReviewReviews (43)

1 - 5 of 18 reviews

Reviewed 1 week ago
Incredible Day - Must Do During Italy Trip!

My wife and I spent 4 days in Florence during our honeymoon, but wanted to see a little more of Tuscany. We did some searching and found this Walks of Italy tour. Please note - this is not a wine tour, but includes lunch and...More

1  Thank bradleystoner
Reviewed 3 weeks ago
My favorite tour we did in Italy!

This was by far my favorite tour we did in Italy. We went in late July and people warned me that it was hot in Italy but I was not prepared for how hot. But at least it wasn't raining! We left around 8:30 in...More

Thank Claire D
Reviewed 3 weeks ago
A beautiful day trip from Firenze--Siena & San Gimignano

My wife and I thoroughly enjoyed the Walks of Italy Small-Group Day Trip to Siena & San Gimignano. Our guide was Ishmael, and he was friendly and knowledgeable. We started with a panoramic view of Florence from Piazzale Michelangelo--a beautiful place to start. From there...More

Thank Jeffrey M
Reviewed 14 August 2018
Perfect tour company to experience Italy!

My family could not stop talking about their experience with the Walks of Italy tour! My husband has been experiencing leg pain recently and was worried about being able to enjoy the tour. The guide (believe his name was Nebo) did an exceptional job of...More

Thank CarolineC4855
Reviewed 17 July 2018
Unforgettable Hidden Italy Self guided walk

My husband and I are in our 60's and decided to do a self guided walk through amazing Tuscan country side from St Gimignano to Siena with the Hidden Italy company. We were a little anxious about getting lost, but preferred to experience the walk...More

Thank Yvonne P
Questions & Answers
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15 September 2018|
Response from Cruiser304828 |
We would like to book the small group tour to Siana, Chianti, Sangimiano with lunch & wine pairing for Monday Sept 24. Is this date available for four adults?
17 July 2018|
Response from DebAW16 | Reviewed this property |
No headset...small group so you can always hear the guide. In our group we had an eighteen year old male who seemed to enjoy the trip. My daughter (29) went on it a week after we did and thoroughly enjoyed the tour.