small group tour

Siena, San Gimignano & the Tuscan countryside

(5 customer reviews)
per person
All health and safety measures are in place. so relax and enjoy your experience!



Enjoy a day trip to Siena & San Gimignano

Join our small-group tour to visit 2 Tuscan gems and an ancient winery: the perfect mix of art, history, gorgeous Tuscan views, food and wine!

See the highlights of Siena on a guided walking tour, admire the marvelous Tuscan landscape, taste genuine local food paired with great wines and finish your day relaxing in the hilltop village of San Gimignano.

Guided visit to Siena

Discover the beautiful art city of Siena with a knowledgeable guide will take you on a walk through the town’s picturesque narrow streets. See the shell-shaped Piazza del Campo, one of the most beautiful squares in Italy, a brick-paved square where the famous ‘Palio’ horserace is held twice a year.

Admire the magnificent Cathedral and the tall and trim Torre del Mangia. After the guided tour, enjoy your free time to wonder Siena at your own pace, to shop around or have an Italian  espresso.

Tuscan countryside and winery lunch

On the way to San Gimignano, admire the unique Tuscan landscape driving through marvelous postcard views surrounded by olive trees, vines and old stone buildings.

Next stop is at a family owned wine estate located in the typical Tuscan landscape with amazing views of vines and olive trees. Here you will have time to relax and enjoy a proper Tuscan lunch that gives you a taste of country hospitality.

The menu includes assorted cold cuts, cured ham, salami, cheeses, bruschetta, pasta, or soup, salad, dessert and coffee, paired with the winery’s own excellent wine, olive oil and vin santo (sweet dessert wine).

San Gimignano

After lunch, we will reach San Gimignano and end the day in complete relax. Famous for its splendid skyline of tall Medieval towers, here you will have free time to explore the main street full of typical shops, have a look at the “Collegiata” (main church), or enjoy a gelato!



Your perfect day trip to Siena, San Gimignano & the Tuscan countryside ends with a comfortable ride back to Florence.

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How much walking is involved in this small group tour?
The itinerary involves moderate walking and a few stairs. It can be covered by all people on average fitness level.

Unfortunately, being a group tour it is not suitable for people with walking difficulties or not able to follow the standard pace of the group.
If you’d like, we can help you with the private version of the Siena and San Gimignano tour.



Can we add the guided visit of Siena Cathedral on the day of the tour?
Surely you can, accordingly to last-minute availability. Simply ask to your guide



For the light lunch, can we have a vegetarian option?
Vegetarian and gluten-free can be catered for upon request at the time of booking.



How long does it take the guided walking tour in Siena?
Approx. 1 hour and 15 mins, and includes all the highlights of Siena from outside.



May I visit the interiors of Siena Cathedral?
Entrance fees of the Cathedral + guided visit can be purchased directly on the day at Euro 15.00 per person. If you are interested, please ask to your guide.
The Cathedral is not accessible on Sundays (due to the Mass) or during celebrations.



Can I buy the Siena Cathedral entrance fee, directly on-site and visit on my own?
Surely you can, according to tickets availability, the queue to buy the tickets and/or enter the Cathedral. Our guides have priority access so you can maximize your time.



Will the guide be with us also in San Gimignano?
The guide will bring you to the very heart of San Gimignano, give you a quick introductory tour and then you will have free time to relax, buy souvenirs and have a gelato.
San Gimignano is a very small village where you can easily stroll around on your own.



Can I join the tour with an infant?
Infants are welcome on this tour! Although they travel for free, they must be confirmed at the time of booking. Infants will seat on the parent’s lap.



You may find additional info on our FAQs page, on the Small Group Tours section

Free date changes

You can change your service date for free, within 24 hr prior departure.

Credit for future tours

You can convert your existing payments to credit, and use it on your next trip, up to 24 hr prior departure

Gift or transfer

You can transfer your credit to a friend or family member, at no extra cost.

Free Cancellation

– Up to 24 hours prior departure time

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5 reviews for Siena, San Gimignano & the Tuscan countryside

  1. CK_C (verified owner)

    Great experience and good value!
    Alessandro (Alex) was a great driver and guide. This itinerary went together very well, with three distinct experiences, but not rushed and all within nine hours.

  2. Jana_A (verified owner)

    Great way to see Tuscany
    We loved this tour! We were lucky to be two of only five people on the tour so took it in a van. Our guide, Alex, gave an excellent walking tour of Siena and also gave us time to explore on our own. We loved the wine tasting and lunch at the vineyard and just seeing how beauty of the Chianti area. Our favorite spot of a great tour was San Gimignano, a small town that still had its medieval towers and architecture.

  3. Sarah_G (verified owner)

    Fun tour!
    This was a nice tour to explore outside of Florence. We saw 2 medieval cities and had a nice tour / lunch at a winery. Alex did a great job showing us around and was a lot of fun!

  4. LeeChin_L (verified owner)

    Great trip
    lorenzo and Andrea from Prestigerent took great care of all of us. Tour was of the right duration and showcased beautiful Siena and the Tuscan country side, plus delicious lunch and wine. Thumbs up!

  5. Timothy_H (verified owner)

    Highly recommended
    Very enjoyable! Only 8 on our tour plus our guide, Alex, who was an excellent host. Arrived in Siena before crowded making it easy to hear Alex’s interesting commentary. Food & wine at winery great and San Gim.. beautiful

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