VIP Small-group Siena and San Gimignano day tour from Florence with dinner

Enjoy this small-group tour which will let you discover the beauties of Siena, San Gimignano and the Chianti countryside, before admiring the sunset on the Tuscan hills and tasting a typical dinner in a fascinating location.

  • enjoy the ride to San Gimignano in our comfortable air-conditioned minivan
  • explore Siena and admire the stunning Piazza del Campo: the setting of the famous Palio horse race in this daily trip from florence
  • book our guided tour with your friends and take marvellous group pictures framed by the medieval buildings of San Gimignano
  • 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 SMALL-GROUP tour - 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


EVERY DAY at 2pm


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.

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.
hen 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 VIP Small-Group Siena&San Gimignano with Dinner in a Chianti Winery provides a quintessential Dolce Vita Tuscan experience which you will never forget.


  • Small-group tour
  • Personalized attention
  • Transportation IN/OUT Florence by comfortable Minivan
  • English speaking driver/tour leader
  • Guided walking tour of Siena with professional English speaking guide
  • Surprise tasting in Siena
  • San Gimignano visit with free time
  • Typical dinner in a fascinating Chianti countryside location
  • Guided visit of the winery cellars
  • Wine tasting
  • Free subscription to our Food & Wine Club (25-Euro value), to access special discounts online on wine and typical products
People on this tour: min1 - max16

Meeting Point

FLORENCETOWN TOURS & NEWS STAND - Piazza della Repubblica (next to the APPLE STORE under the loggias, corner with Via Pellicceria) - Florence - SEE ON MAP


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

Rain Policy

This tour runs rain or shine.

User review

| Total reviews for this tour: 65
Merry M
5 Jun 19

Outstanding trip

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.

1 May 19


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

21 Jul 18

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 small group and our guide was excellent and we never felt of our highlights...

Dena P
2 Jul 18

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 Luca!

21 Jun 18

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 had a nice relaxing atmosphere. Overall a great experience and we highly recommend this tour!

24 May 18

Nice day and nice people

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 169

EUR 169 p.p. (adults)
students 10% disc. / children 6-12 50% disc. / children 0-5 FREE

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