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Depart from central Florence and venture into the Tuscan countryside, a beautiful landscape marked by olive groves, green hills and cypress trees.

Arrive first in Siena, one of Tuscany’s crown jewels. Follow a local guide on a walking tour through the city, passing charming backstreets as well as Piazza del Campo, the celebrated main square that hosts the Palio horse races twice a year. Learn about Siena’s contrades, or districts, which each have individual legacies, traditions and anthems. Before departing, sample a surprise local specialty.

Continue to the hilltown of San Gimignano, known for its impressive towers. Relax with some time to roam the streets independently, popping into local shops or admiring the medieval architecture.  

Afterward, travel to a Chianti winery to soak up the sunset while eating dinner. Weather permitting, take a seat outdoors and feast on a 3-course meal of authentic Tuscan dishes with wine.

After a day of food, wine and sightseeing, you will be returned to central Florence.
Locations visited
Piazza del Campo
Piazza della Repubblica
Get a true taste for the Tuscan countryside with this day trip to Siena, San Gimignano and a Chianti winery for dinner. Departing from Florence, venture first to the city of Siena for a guided tour through the Piazza del Campo, the site of the renowned Palio horse races, as well as a surprise food tasting. Afterward, wander the hilltown of San Gimignano before heading to a Chianti winery for a delicious 3-course dinner, complemented by fine local wine. Your trip is reserved to 16 people to keep the experience intimate.
  • 8-hour Siena and San Gimignano tour with dinner in Chianti
  • Leave Florence and travel through the Tuscan countryside to Siena
  • Take a Siena walking tour around Piazza del Campo and the city’s picturesque streets
  • Make the most of some free time in the hill-town of San Gimignano
  • Visit a Chianti winery at sunset and savor a 3-course meal with wine, dessert wine and cookies
  • Small-group experience with a maximum of 16 people ensures personalized attention
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1 - 5 of 8 reviews
Reviewed 3 weeks ago via mobile
Italy trip

Loved this tour... picked up in Florence 2pm we rode in a van to visit Siena an San Gimignano then to the vineyard for a tour and dinner...arrived back in Florence with a surprise to see Florence by moonlight from Piazza Michaelangelo. We enjoyed the...More

Thank ter824ena
Thomas V, Guest Relations Manager at FlorenceTown, responded to this reviewResponded 3 weeks ago

Dear Ter824ena, we are very happy to read that you enjoyed our Guided Tour of Siena & San Gimignano so much to write this great review and feedback, this is a fundamental instrument to maintain our high standard of quality and guests' satisfaction! We hope...More

Reviewed July 10, 2018
Amazing overall experience and Fabulous tour guides!

Veronica was our driver and wine tour guide - SO fabulous! We visited Siena and San Gimagnano and ended our day with a 3 course Tuscan dinner with wine and olive oil tasting. Could not have asked for a better day! She was knowledgeable, funny...More

Thank Kristen B
Thomas V, Guest Relations Manager at FlorenceTown, responded to this reviewResponded July 12, 2018

Dear Mrs. Kristen B. , we are glad to read that you chose Florencetown for your stay in Tuscany, and we also appreciate the time you spent writing the review. Thank you for your suggestions, since this is the most important instrument in order to...More

Reviewed July 2, 2018
Great Experience and Tour Guides

My family and I really enjoyed this tour. Our driver/tour Guide Luca was informative, accommodating, and a genuinely kind person. The food at dinner was also amazing! I highly recommend this tour to anyone interested in the history of Tuscany and a great meal. Request...More

1  Thank Dena P
Thomas V, Guest Relations Manager at FlorenceTown, responded to this reviewResponded July 2, 2018

Dear Dena P. , It is a real pleasure to read that you chose Florencetown for your stay in Florence, and we also appreciate that our tour and guide Luca managed to make you spend a great experience in Tuscany. We hope you will be...More

Reviewed June 21, 2018
Beautiful Siena and San Gimignano - Worthwhile Tour

Eleonora was our tour guide and driver for the day. She did an amazing job explaining the history of the towns while driving through the beautiful landscape of Siena and San Gimignano. The dinner at Relais Villa Olmo in the Chianti region was delicious and...More

1  Thank hannumrw
Thomas V, Guest Relations Manager at FlorenceTown, responded to this reviewResponded June 25, 2018

Dear Hannumrw , we are pleased to read that you enjoyed our Siena and San Gimignano By night tour, and that this experience managed to make you spend a lovely time! We will also report this message to Eleonora, since she will be happy and...More

Reviewed June 18, 2018
Overall a very disappointing and frustrating experience.

The 8 1/2 hour trip included a 1 1/2 hour tour of Siena which was beautiful and we really enjoyed the young woman who was our guide, she was very informative. It also included 1 hour of free time in San Gimignano to walk and...More

Thank Mary O
Marusca I, Marketing Manager at FlorenceTown, responded to this reviewResponded June 21, 2018

Dear Mary O, first of all thank you for choosing a Florencetown tour. We appreciate the time and effort you have spared to give us this review. We always accept all reviews as an essential element in our strive to continually maintain and exceed expectations,...More

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