Shared Semi-private

The best Siena and San Gimignano tour from Florence with dinner

Florence to Siena day trip including time in San Gimignano and a tasty typical dinner

  • Florence to San Gimignano: book our guided tour with your friends and take marvellous group pictures
  • Siena and San Gimignano tour from Florence: explore two gems of Tuscany
  • Florence to Siena day trip: enjoy the ride in our comfortable air-conditioned minivan
  • our afternoon tour will let you feel the unique atmosphere of San Gimignano by night
  • avoid the crowd visiting some of the most iconic locations with this afternoon tour from florence
  • the famous Palio di Siena will have no more secrets with our guided walking tour
  • get lost in the narrow streets of San Gimignano: the real image of a Tuscan hill town revealed by our day tour
  • the skyline of San Gimignano is stunning: the medieval tower houses untouched by time will make your journey in Tuscany unforgettable


  • VIP Semi-private Siena and San Gimignano tour from Florence - ensures personalized attention
  • Visit two true gems of Tuscany: SIENA, with a professionally guided walking tour, and SAN GIMIGNANO
  • Avoid the crowds leaving in the afternoon
  • Gaze in awe at the Tuscan countryside at sunset
  • Enjoy a delicious typical TUSCAN DINNER with wine tasting in a fascinating Chianti countryside location
  • Only in English to preserve the quality of the tour


March 2022, and Nov 2022 to Feb 2023: Mon, Wed and Fri at 2.00pm / from April 2022 to Oct 2022 Everyday at 2.00pm


Approx. 8 hours






A fabulous and exclusive all-round Tuscan extravaganza!

Spend an enlightening afternoon visiting Siena and San Gimignano, two of Tuscany's "jewel cities", and top the day off with sunset and dinner in a boutique winery in the rolling Chianti countryside.

From Florence to Siena day trip in full comfort aboard our state-of-the-art minivan, with your dedicated English-speaking driver and tour escort.
Set in a beautiful landscape, surrounded by vineyards and olive groves, Siena is one of the most enchanting medieval cities in Italy.
Led by a specialized knowledgeable guide you will discover the town's most striking sights, admire the marvelous Piazza del Campo - where twice a year dashing horses compete in the heart-rendering Palio race -, explore quieter backstreets and learn everything about the Contrade, the 17 medieval city districts that compeat against each other in the Palio.

Then travel on to San Gimignano, UNESCO World Heritage Site and one of the most splendid examples of an ancient walled town. Renowned as “the city of beautiful towers” or "Tuscany's Manhattan" it boasts an exceptional skyline, is certainly one of the most well-preserved towns in the whole of Italy and has, in fact, been used as a background in many movies. During your free time here, stroll the maze of quaint cobblestone streets at leisure, discovering the many tall towers, once homes, which characterize the town.

Breathe in the authentic atmosphere and then set off, to admire the sun setting over the vineyard-clad Chianti hills and savor a genuine Tuscan dinner and wine tasting in the charming premises of a delightful boutique winery.
Enjoy the scrumptious flavors of an authentic typical meal splendidly paired with different excellent wines, as well as the privilege of a private visit to the estate's wine cellar.

Leaving you free to relax in the morning, and leading you into the heart of Tuscan beauty and heritage in the afternoon and evening, our Small-group Siena and San Gimignano tour from Florence provides a quintessential Dolce Vita Tuscan experience which you will never forget.

Please note that this tour might be ran on Mercedes luxury 8-seater vans or Mercedes luxury 20-seater minibuses in order to comply with Covid-19 safety rules, possibly varying the size of the group, and always providing the highest possible quality.


  • Transportation IN/OUT Florence by comfortable Minivan
  • English speaking driver/tour leader
  • Guided walking tour of Siena with professional English speaking guide
  • San Gimignano visit with free time
  • Typical dinner in a fascinating Chianti countryside location
  • Guided visit of the winery cellars
  • Wine tasting
Suitable for vegetarians! (please inform us in advance)

Meeting Point

FLORENCETOWN BOOKING OFFICE - Piazza Mentana 2red - Florence - SEE ON MAP


We regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobility.

Please note that this tour might be ran on Mercedes luxury 8-seater vans or Mercedes luxury 20-seater minibuses in order to comply with Covid-19 safety rules, possibly varying the size of the group, and always providing the highest possible quality.

Rain Policy

This tour runs rain or shine.

User review

| Total reviews for this tour: 72
“This was an excellent tour. it provided a nice escape from the city, and introduced us to very interesting information about different ways to produce wine.”
“We spent the day with Eleonora and couldn't have enjoyed it more! The tour was casual and informative with fun at every turn! Our guide in Siena, Maria, was fantastic! Wine tasting and dinner were the perfect ending to a perfect day! Patti and Kathy”
“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 small group and our guide was excellent and we never felt of our highlights...”
“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 Luca!”
“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 had a nice relaxing atmosphere. Overall a great experience and we highly recommend this tour!”
“Very nice driver-guide and a lot of interesting activities, small group (in English). Sienna was a beautiful city.The stop at San Gimignano was a little too short but intresting. The diner was ok (i would have appreciated more dessert). Overall, a good day”
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from 199

EUR 199 p.p. (adults)
children 4-12 30% disc. / children 0-3 FREE

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