• Location: Florence, Italy
  • Duration: 11 hours (approx.)
From USD $ 224.16 View price calendar

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Experience the architecture, landscape and local flavors of Tuscany on a day trip departing from Florence. Led by a professional driver-guide, visit San Gimignano, Siena, Monteriggioni, Pisa and Chianti’s famous wine region, soaking up each town with a walking tour. Admire the Leaning Tower of Pisa, the Siena Duomo and relax with lunch and a Chianti wine tasting on this comprehensive exploration of Tuscany. This small-group tour is limited to eight people to ensure an intimate experience.


  • Full-day tour of Tuscany and Chianti from Florence, led by an expert driver-guide
  • Admire famous Italian monuments including Siena Duomo and Palazzo Comunale
  • Stop for lunch at a Chianti country estate to enjoy local delights
  • Sip on glasses of iconic Chianti and vernaccia wine during a wine tasting at the estate
  • Strike a pose for photos by the Leaning Tower of Pisa, a UNESCO World Heritage site
  • Small-group tour with a maximum of eight people ensures personalized attention

What You Can Expect

Pisa, Siena, San Gimignano, Chianti and Monteriggioni Small-Group Tuscany Day Trip

Visit Piazza del Campo where the annual Palio di Siena horse race takes place

Your day trip will begin with pickup in central Florence. Join up with your guide and hop aboard your minivan as you begin your journey out of the city. Watch as the scenery changes from urban streets to the rolling hills of the Tuscan countryside.

Arrive in Siena after an hour’s drive, taking off independent walking tour at your own pace. Pass the central hub of Piazza del Campo, home of the city’s famous Palio di Siena horse race. Admire the square’s architectural gems, including the Torre del Mangia, Palazzo Comunale and the stunning striped marble of the Siena Duomo. Enjoy some free time to explore on your own before hopping back on the road.

Travel past the olive groves and grapevines of the Chianti region to Monteriggioni, a fortified town constructed in the 13th century. Peer up at its impressive towers, 11 in total, and stroll around the medieval walls.

Continue back into Chianti, stopping at a rustic estate for lunch. Savor a Tuscan spread of Pecorino chesse, salami, bruschetta and seasonal ribollita, a hearty vegetable and bean soup native to the region. Complement your feast with top Vernaccia and Chianti wine (see the Itinerary section below) as the estate’s owner educates you on these prestigious blends.

After a finale of almond cookies and dessert wine, head to the hill town of San Gimignano. Stroll through the UNESCO-listed Old Town to discover a trove of architectural treasures: Palazzo del Podestà, Piazza della Cisterna, the ‘dome of San Gimignano’ and the Church of St Agostino.

Soak up a final visit to Pisa to take photos of the famed Leaning Tower, along with the Pisa Duomo and the Baptistery. Your day trip will conclude with drop-off back in central Florence.

Customer Reviews

Christina G

5 star rating: Highly Recommended September 2017

Small group made for a very personalized experience. I had my children with me and they were wonderfully accommodated.
It was great.

Julian D

5 star rating: Highly Recommended September 2017

Amazing tour, was worried that each site would be rushed but only Sienna was too much. Just enter the basilica as the museum will take too much time. Our guides name escapes me but he was incredible, very knowledgeable about the places and history of area and visited sites

Lanx G

5 star rating: Highly Recommended July 2017

One of the most amazing tours that I had ever went. Highly recommended. The driver was very professional and nice. He ensured that we had the best experience instead of rushing us. The lunch was local and traditional. I miss all the places so much. We had a small tour with another couple so it felt like a private tour. Pisa tower has a long queue but the driver can help you to time it so you go at the end of the day. Also try to go on a weekday instead of a weekend. If not, you might have enough time to go up to Pisa tower.


5 star rating: Highly Recommended March 2017

Honestly a highlight of our Italy trip. Don and #39;t quite understand some of the negative reviews. Sergio, our driver, was very friendly, talkative and gave nice background for all stops. Each stop was perfect time. We were group of 4 with a 5 and 7 year old. Nice large lunch and wine. Recommend!

Janice B

5 star rating: Highly Recommended June 2016

Had a super day, great guide, very knowledgeable and friendly, a must


5 star rating: Highly Recommended December 2015

We highly recommend this small-group trip. As there was just one other person with our family of 3, we got to see so much in a day. The Chianti region is so beautiful. Our guide, Aldo was a fantastic guy. We learnt a lot about Tuscany in just one day!


5 star rating: Highly Recommended November 2015

This was a great day trip from Florence! Plenty of time to walk around Sienna and Pisa. Wine tasting was very enjoyable. Great views of the hills of Tuscany from San Gimignano and Monteriggioni.

Arthur S

5 star rating: Highly Recommended October 2015

Great tour. Small group at the wine tasting and lunch was terrific.

Andrew S

5 star rating: Highly Recommended August 2015

Amazing day. Very impressed with the tour, saw a lot and it didn't seem like a long day.

Andrew L

5 star rating: Highly Recommended June 2015

This tour is fabulous and a great way to see Tuscany. The lunch including the wine tasting was the highlight as was our tour guide Aldo - he was fastastic

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