Shared Small-group

Siena and San Gimignano tour with dinner in Tuscany at a boutique winery - shared tour

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

  • 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 small-group Siena and San Gimignano tour from Florence
  • Visit two true gems of Tuscany: SIENA, with a professionally guided walking tour, and SAN GIMIGNANO
  • 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


from NOV to MAR: Mon, Wed and Fri at 1.00pm / From APR to OCT every day at 2.00pm


Approx. 8 hours






A fabulous and exclusive all-round Tuscan extravaganza: a day tour from Florence to Siena and San Gimignano!

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.

Depart Florence for Siena in full comfort aboard our state-of-the-art minivan, with your dedicated English-speaking driver and tour escort, and reach Siena.
Set in a beautiful landscape, surrounded by vineyards and olive groves, it 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) and enjoy a flavorful surprise: a tasting of a local specialty.

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", San Gimignano boasts an exceptional skyline and it is certainly one of the most well-preserved towns in the whole of Italy, 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.

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 VIP Small-Group Siena and San Gimignano in one day tour provides a quintessential Dolce Vita Tuscan experience which you will never forget.


  • Return transport from Florence in comfortable minivan
    English speaking driver/tour leader
    Guided walking tour of Siena with professional guide
    Surprise tasting in Siena
    Visit of San Gimignano with free time
    Typical Tuscan dinner in a boutique winery in Chianti
    Guided visit of the winery cellars
    Wine tasting

Meeting Point

The meeting point is in our booking office in Piazza Mentana 2red, Florence (opposite the Arno River). - SEE ON MAP


Please inform us of any food intolerance or allergy in advance.
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 run on Mercedes luxury 8-seater vans or Mercedes luxury minibuses according to the tour occupancy 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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