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Delve into the cultural and natural splendor of charming Italian towns, Siena and San Gimignano, on a full-day trip from Pisa. Opt to travel with or without a knowledgeable guide, and then set out to visit some of the region’s most spectacular sites. Cruise past bounteous vineyards, stopping to taste the local produce at a traditional winery; explore the ancient medieval town of San Gimignano, soaking up sweeping panoramas from its hilltop perch; and discover the UNESCO World Heritage-listed monuments of Siena on a guided tour of the historical city. Receive personalized attention from your guide on this small-group tour, limited to only seven people.


  • Full-day tour to Siena and San Gimignano from Pisa
  • Travel by air-conditioned minivan through breathtaking Tuscany, either independently or with a guide
  • Visit the UNESCO World Heritage sites of Siena and San Gimignano
  • Admire Siena Cathedral and Piazza del Campo
  • Savor two Tuscan wines at a local winery

What You Can Expect

Small Group Pisa Day Trip to Siena and San Gimignano by Minivan Including Wine Tasting

Admire the Mangia Tower in this small group tour from Pisa

Depart from your Pisa hotel in a comfortable, air-conditioned minivan destined for the UNESCO World Heritage-listed city of Siena. During the 1.5-hour journey, admire the stunning scenery of the Tuscan countryside and then disembark on arrival in Siena, a city that seems to be frozen in time. 
Stroll the city on a guided tour, if the guide option was selected at booking, or explore streets shrouded in artistic heritage independently. Marvel at the grand stature of the 13th-century Siena Cathedral, a structure that boasts a façade considered one of Italy’s finest; absorb the atmosphere of the Piazza di Campo, around which the entire city is built; and admire the sacred Battistero di San Giovanni (St Giovanni Baptistery) during your exploration. 
Travel onward to San Gimignano, a UNESCO World Heritage-listed site home to 13 imposing stone towers nicknamed ‘Medieval Manhattan’. Stroll the quaint cobbled streets and allow your attention to be directed to some of the finest ancient architecture in Tuscany. 
Conclude your comprehensive tour with a relaxed wine tasting session at an ambient wine cellar near San Gimignano; converse with your fellow travellers and listen as your guide provides fascinating commentary on Tuscany’s rich history. 
Sated by two complimentary glasses of wine, relax during the journey back to your Pisa hotel, where the tour concludes.

Customer Reviews

Robert L

5 star rating: Highly Recommended October 2016

Aviator Bellaitaliatours was a last minute decision and we were pleasantly surprised. They are professional, efficient, knowledgeable and their guides wonderful. San-Gimignano in the morning. Siena in the afternoon. Both old towns on hill within medieval walls and picturesque. Then wine tour in renovated farm house where the wine and olive oils are produced from their own land organically. Memorable day. Spectacular scenery. Thank you Luca our guide for a wonderful experience.


5 star rating: Highly Recommended August 2016

Fantastic trip and it is from the best tours I did in my life. I traveled so much abroad in tours and until now I didn't find tour guide better than Lucca, he explained everything to us and he was nice,very friendly and he made our trip so perfect. we want to the beautiful San Gimignano and Sienna and it was such a good places to visit. Wine tasting was awesome too with bread and above it the verging olive oil and sheep cheese.
Everything was on time, so it is very good trip and I recommend it to everyone.

Scott M

5 star rating: Highly Recommended August 2016

Almost a perfect trip. The driver arrived right on time, and chatted with us for the whole journey, explaining the route, the history of the region, and background on Tuscany. His knowledge was unbelievable. The stops were just the right length and the wine tasting at the local farm was excellent. I was initially hesitant about taking a trip like this, but it was well worth setting aside a day for it. Next time there will be other trips too!


5 star rating: Highly Recommended June 2016

Excellent although we would have liked more time in San Gimignano. Luca the guide was superb.


5 star rating: Highly Recommended May 2016


Miriam O

5 star rating: Highly Recommended October 2015

A fabulous trip and our driver Michele Michael was excellent, very helpful and informative. Both places are different but well worth a visit and the location where we had the wine tasting was stunning!

Gill M Edwards E

5 star rating: Highly Recommended October 2015

Excellent trip to take. Every aspect was so well organised and timed to perfection. The guides were fantastic and made a great trip a fantastic event. Well worth doing and don't forget to try the gelato !!

Kevin H

5 star rating: Highly Recommended March 2015

Fabulous day trip , both guides were informative and helpful. Day was well organised and very enjoyable ,would thoroughly recommend it .

Maria B

5 star rating: Highly Recommended February 2015

Our driver Michele was lovely and well-informed and provided maps to make sure we didnt get lost. The tour provided a good amount of time at the locations to see the cities, buy souvenirs and have a bite to eat. Our guide in Siena, Ciara, was bubble and funny and explained the history of the city and there culture beautifully. Wine tasting was lovely and again well-informed and such fun. Highly recommend this tour - the countryside is stunning, the towns are stunning and the people were all so helpful and friendly. A truly enjoyable experience.

gina M

4 star rating: Recommended June 2016

We really enjoyed this tour and would recommend the tour to our family and friends. We were picked up on time and enjoyed the history and details shared by our knowledgeable guide during the drive and in San Gimignano. We liked there was a lot of flexibility to the tour including time to explore on our own. Although there was a lot of driving, we enjoyed the Tuscan sights, absolutely fantastic!

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