Day trip

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Activity provider: My Tour in Italy
Day trip

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Activity provider: My Tour in Italy
Save up to 15%

From US$ 72.66 US$ 61.76 per person

Enjoy a full-day tour of Tuscany’s villages and wine regions in the heart of the Tuscan countryside. Visit San Gimignano and the medieval town of Siena.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 11.5 hours
Check availability to see starting times.
Live tour guide
English, Spanish, Portuguese, Chinese, Italian

What customers loved


9 hours
  • Florence

  • 1 hour
  • San Gimignano (free time)

  • Monteriggioni Castle (free time)

  • Poggibonsi (wine tasting)

  • Siena (guided tour, free time)

  • 1.5 hours
  • Florence

Meeting point
Main stop
Other stop
  • Escape the bustle of Florence for a day and explore the beautiful Tuscan countryside
  • Drive through the gently rolling hills of the Val D’Elsa in luxury, air-conditioned coaches
  • Visit the medieval town of San Gimignano, home to Vernaccia di San Gimignano wine and saffron
  • Explore the immaculate town of Siena, world-renowned for its Palio horse race
  • Visit a splendid Chianti estate and take part in two exclusive wine tastings
Full description

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano.

Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa.

Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets.

Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background.

Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico.

Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

  • Air-conditioned bus or minivan
  • Multilingual guide
  • Lunch stop (if option chosen)
  • Guided tour of Siena (if option chosen)
  • Free time in San Gimignano
  • Visit to the Monteriggioni fortress
  • Wine tastings
  • Guided visit of a Chianti estate
  • Entry to Siena Cathedral
  • Entry to Palazzo Comunale
Not suitable for
  • Wheelchair users

Select participants and date



Meeting point

Meeting point may vary depending on the option booked.

Important information

What to bring

  • Comfortable shoes
  • Credit card
  • Comfortable clothes
  • Packed lunch
  • Cash

Know before you go

  • This tour will be conducted in multiple languages at the same time, but only English is guaranteed for the guided tour of Siena
  • The tour itinerary may change according to the season and unforeseen circumstances
  • Customers must be able to climb and descend stairs
Customer reviews

Overall rating

4.4 /5

based on 3161 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

Sort by:

Traveler type:

Star rating:

Thanks Daniel for taking our small group on this tour. We loved all the medieval towns and the winery. The tour information was perfect! Please do not include the lunch, it was not worth it. Rather walk into the less touristy areas and enjoy fresh Italian food. The restaurant we visited served old tomato on dry bread, tasteless pasta. We left before dessert. Unfortunately this sometimes happens at restaurants close to Famous landmarks.

Read more

March 29, 2023

The best tour we take in Italy. It was a complete experience, beyond expectations and fantastic value. Our guide delighted us with his knowledge and showed us scenic views that we couldn't see if we had decided to go for ourselves. I also recommend you add the lunch at Siena; you will receive a delicious 3-step meal.

March 29, 2023

The original tour that I booked is cancel due to not enough people. They offered me to join another tour which include Pisa, wine tasting and lunch at no extra cost. Some confusion of where to meet the driver in the beginning. We have to call the customer service to find out the actual meet up point is in front of the café main entrance. It was a 7 seater Mercedes van. First stop at Pisa, then went straight to wine tasting and lunch. One of the best wine tasting I ever had. The host was very generous, had four types of wines with vinegar, cheese, bread, ham. Lunch was simple but delicious pasta. Take note that there's isn't a tour guide. The driver will explain a little history along the way but you will be on your own to explore. Reached San Gimignano around 4pm and we only have one hour 15 min there. It's already getting dark. Wish that remove Pisa and spend more time at Siena and San Gimignano. These two places deserve more times. Overall I'm quite satisfied with the tour.

Read more

March 29, 2023

Product ID: 7679