• Location: Florence, Italy
  • Duration: 8 hours (approx.)
From USD $ 83.34 View price calendar

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Venture to the notable wine regions of Tuscany on this private day trip, departing from your Florence hotel. Your personal guide shows you around the medieval village of Monteriggioni and takes you to Siena where you'll meet a local guide for a walking tour of the city center. After a stop in San Gimignano head to Chianti for an included wine and food tasting. Pricing is per group, based on a maximum of eight people.


  • Tuscany tour with wine tasting, round-trip from Florence
  • Visit Monteriggioni, Siena, San Gimignano and Chianti
  • Local guide on a walking tour of Siena
  • Food tasting includes bruschetta and salami
  • Private tour is operated with just your party and a driver
  • Hotel pickup and drop-off included

What You Can Expect

Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

View of San Gimignano from the vineyards.

Depart Florence in the morning with pickup from your centrally located hotel, then settle in the comfort of your private vehicle during the drive to Tuscany. The fortified 13th-century village of Monteriggioni is the first stop on your personalized tour of Italy's famed wine region. The hilltop town offers panoramic views that stretch from Florence to Siena, your next destination. 

On arrival in the brick-walled town with its distinctive tower, meet a local guide for a walking tour. Stroll through Siena's historical center and include visits to the Piazza del Campo and the Italian Gothic cathedral at the Palazzo Pubblico. 

Leaving Siena behind for San Gimignano, you'll notice the pretty town's 13 towers from a distance. Relax as you amble past the weathered stone buildings and discover the town's hidden gems — it's an ideal place to purchase a meal accompanied by a glass of wine (own expense). 

Then set off for Chianti for a tour of a local winery and get a sense of traditional Tuscan life. Learn how wine is processed and produced, and sample a variety of wines during an included wine and food tasting. Afterward, you're dropped off at your hotel in Florence.

Customer Reviews


5 star rating: Highly Recommended March 2017

Wonderful tour, our driver Placido was great and gave us so much info along the way. We loved Sienna and San Gimignano. The wine tasting was so much fun!

Teresa L

2 star rating: It was OK, but could have been better June 2017

The pros: Tuscany is beautiful and the weather was amazing. The van was clean and we felt safe throughout the entire tour. We were traveling with my older father who uses a walker, and our driver was very accommodating in helping us load/unload and to drive him to the tops of hills/etc to limit walking. The short walking tour in Siena was great and we learned the most during this short walking tour which was led by someone in affiliation with our booked Viator tour. She was fantastic!!!
The cons: There is a lot of ground to cover on this tour. Probably too much, especially when your driver takes you to two wineries without us asking to do so versus the published one expectation. I know... it sounds like we shouldn't be complaining - right? But, we rushed from place to place and were disappointed that we had such little time in Monteriggioni and San Gimignano. After returning home that evening, we re-read the tour description and learned why we were so rushed throughout the day - our driver had added a stop at an additional winery earlier in the day. When we arrived at this winery, we had no idea that is wasn't the one that was included in our package. He didn't tell us. The package says that a wine tour, tasting, and light food would be included in our winery stop. We assumed this was it. It wasn't. We certainly had sticker shock when we received our wine tasting and lunch bill that was 200e. We knew that lunch was not included in this tour, but we were ushered into this winery and assumed it was our included snack and tasting. We didn't order any food, it was simply brought out to us. Our stops in Monteriggioni and San Gimignano included 30-45 minutes of free time at each place. That's not even enough time to walk through the squares/etc. Very rushed. When we asked to just stay at San Gimignano for more time, we were told that we had already paid for the winery stop on the way home. So... this winery stop was the one we paid for. It did include the wine tasting and light food. We purposely picked this tour and it wasn't cheap so that we could see the area and enjoy the towns. If we wanted a multiple winery tour, we would have booked that. We spent about 3 hours total within Monteriggioni, Siena, and San Gimignano and the rest of the day was driving fast and rushed or spent at wineries. Minimal discussion about what we were seeing and the historical significance as we went from place to place.
This was my parents first and most likely only trip to Tuscany so we were disappointed at the rushed experience throughout the day.

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