• Siena Cathedral
  • Tour of Siena and San GImignano
  • Visit San Gimignano
  • Dinner in Chianti
Small-group (Up to 16 people)

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

5,0 / 5 (29)

See two of Tuscany’s most beautiful medieval towns with a stop at a boutique winery for dinner. You’ll go from Florence to Siena then San Gimignano and it’s sure to be an unforgettable day.


About this tour:

8 hours
Live tour guide
Our expert guides selected for you
Personalized attention
Experiences designed for you needs
Instant confirmation

Guaranteed Departure

Likely to sell out

Limited availability

  • Take a walking tour of Siena and discover the Piazza del Campo
  • Marvel at the medieval skyscrapers of San Gimignano
  • Gaze in awe at a sunset in the Chianti hills
  • Discover a boutique winery in the heart of Tuscany
  • Enjoy a traditional Tuscan dinner with a wine pairing

Enjoy a tour which will lead you to discover the beauty of Siena, San Gimignano and the Chianti countryside. Not only that, you’ll enjoy the stunning sunset over the countryside from a boutique winery before rounding off the day with dinner in Tuscany before you return to Florence.

Explore Siena on a guided tour

Back in ancient times, the only city in Tuscany able to compete against Florence for power was Siena. You’ll be picked up in the morning in a comfortable air conditioned minivan which will whisk you from Florence to Siena. Once you arrive, you’ll enjoy a guided walk tour of the compact city, discovering Piazza del Campo, where the famous Palio horse race takes place every year. Your expert guide will tell you all about the story behind the Palio, and the 17 medieval districts that historically competed against each other. Before leaving Siena, there will be a stunning surprise tasting for you!

Be awestruck by the medieval skyscrapers of San Gimignano

The next stop after the guided tour of Siena will be San Gimignano, where you will have free time. San Gimignano has one of the most distinctive skylines in Italy. The small hilltop village in the heart of Tuscany has several towers which have stood for hundreds of years. There’s no direct train line, and many ask how to go to San Gimignano from Florence? This tour includes San Gimignano, and you’ll have some time to wander around at your leisure, discovering its history, traditional products and you could head to the top of one of the towers if you’re feeling brave. The views are certainly worth it!

Round off the day with a sunset and traditional dinner

Florence to San Gimignano isn’t the end of the tour - from the medieval village you’ll carry on to a boutique winery in the Chianti countryside. Be enchanted by the sun as it sets behind the Tuscan hills, a picture you’re sure never to forget. But that’s not all! You’ve still got a traditional dinner in Tuscany coming up with pairings selected by experts at the winery. And of course, you’ll have the opportunity to visit the cellars too. A wonderful and complete experience of Tuscany!


Important Information

Please note that Italy's law doesn't permit selling alcoholic beverage to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.
Please let us know in advance any special need or impaired mobility of the clients and we will do our best to accomodate them.

Rain Policy

This tour runs on rain or shine.


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).

Find here the details of the private tour for a more intimate experience.
private upgrade

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price per person