San Gimignano, Siena, Monteriggioni, Chianti Day Trip With Lunch & Wine Tasting

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Free Cancellation
  • Instant Confirmation
  • Lowest Price Guaranteed
  • Duration: 11 Hrs
  • Language:
  • Departure Time :
    8:30 AM
  • Departure Details :
    Piazzale Montelungo, Firenze FI, Italy
  • Return Details :
    Returns to original departure point
  • Cancellation Policy :
    For a full refund, cancel at least 24 hours in advance of the start date of the experience. Tours booked using discount coupon codes will be non refundable.


Visit two highlights of Tuscany, the charming cities of Siena, San Gimignano and Monteriggioni with this action-packed day trip from Florence. After traveling through the gorgeous Chianti countryside, visit the old town of Siena with its historic city center. Learn about Siena's famous 'contra de' neighborhoods on a visit to one of the city's Contrada museums, and then head to San Gimignano. End your trip by visiting ancient cellars and sampling delicious local wine and snacks with a stop in a typical winery and then in the Chianti area.


  • Day trip (destination A to B)
  • All entrance fees included

Know More about this tour

This is a typical itinerary for your trip to San Gimignano, Siena, Monteriggioni, Chianti -

Stop At: Historic Centre of San Gimignano, San Gimignano, Tuscany

Chianti Hilltop is the pretty medieval village which is also famous for its towers. You will have a great time exploring this area. 

Duration: 1 hour

Stop At: Piazza del Campo, Siena, Tuscany

Guided tour of the historic center, starting from its most beautiful square, Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point and a pleasant walk through the narrow medieval streets of the city, flanked by splendid palaces and historic shops

Duration: 45 minutes

Stop At: Palio di Siena, Siena, Tuscany

The Museum of a Contrada, as well as its Oratory, is the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art, which are normally not disclosed to the public

Duration: 30 minutes

Stop At: Duomo di Siena, Siena, Tuscany

The spectacular Cathedral of the 12th century, of which we can admire the magnificent architecture and the splendor of the polychrome marbles. Interior visit depending on the selected option.

Duration: 30 minutes

Stop At: Monteriggioni, Monteriggioni, Tuscany

The charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day

Duration: 30 minutes

Stop At: Chianti Road, Tuscany

Then crossing the gently Chianti rolling hills, arrive at a cozy Winery, where you will get to taste four fantastic wines and sampling balsamic vinegar and zero food miles products. It is a perfect way to end this memorable experience in the heart of Tuscany with delicious Tuscan flavors!

Duration: 1 hour


Please note: When the Museum and the Oratory of the Contrada are not accessible, it will be replaced with  another site of particular historic and cultural interest.


Guided visit in Contrada's Museum and Oratorio

Licensed tour escort with live commentary on board

Transport by G.T. air-conditioned vehicle with WIFI on board

Visit of a picturesque Chianti medieval village, famous for its colors and charm

Shared or Private Professional guide in Siena (depending on the selected option)

Stop at a typical Winery with tasting of excellent Chianti wines and typical products

Siena Cathedral interior Guided Visit including entrance fee (depending on the selected option)

Entry/Admission - Palio di Siena

Entry/Admission - Duomo di Siena



Hotel pickup and drop-off

Additional Info

Stroller accessible

Infant seats available

Not wheelchair accessible

Near public transportation

Moderate physical fitness level is expected

Confirmation will be received at the time of booking

Dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.

This tour/activity will have a maximum of 50 travelers.

Traveler Reviews

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  • 25-Feb-2020

    We had a terrific time. San Gimignano was a cute town to walk around in the morning. Monteriggioni was tiny. Not much there. It would be better to skip this and have more time in San Gimignano. Siena is marvelous. We have seen a lot of churches but the Duomo is breathtaking. Our guide in Siena, Camilla, was especially good.

    The food and wine at lunch was delicious. We didn’t buy any of the products from the winery because the prices were really high.

  • 06-Jan-2020

    Really wanted to take a trip to the Tuscan country side but did not want to worry about transportation. This trip gave us the opportunity to visit 3 cities plus a winery with lunch. This trip served it's purpose for getting us to and from the locations. Our guide was fine-- not overly enthusiastic in general but was informative. She made sure we were all safe and communicated updates and information about where we were. Since there were both english and spanish speakers on the tour, she communicated in both languages. Unfortunately, our tour got to the cities early in the morning and nothing was open so it was hard to enjoy the cities to their fullest potential given this (this is not the tour's fault, this is just the time of year-- low season).

    The winery was by far the best part. Lunch was spectacular and the wine was incredible. After lunch we went to Siena. Our guide there was very informative and we enjoyed our time, we were just a bit sleepy after the delicious food at the winery and all of the wine.

  • 25-Dec-2019

    This was a great tour and a good way to see a lot of small towns in Tuscany. The lunch and wine tasting was fun too, it was very filling the lunch. Unfortunately we had hit some traffic and our time in some of the towns was shortened (which was out of the tours control). I do wish that we had an actual tour guide in San Gimignano and Monteriggioni because we were kind of just set free, but the free time was nice cause most tours normally don't give much free time. The tour in Siena was very informative and interesting.

  • 04-Dec-2019

    Another reviewer said you should be "moderately fit" for this tour. But even the 20 year old college students were exhausted by the time we finished in Siena. First stop was San Gimignano, which by itself would be worth the trip. Monteriggioni was not worth the stop. The winery tour and lunch was better than I expected, but left us sleepy and lethargic - not the state to be in when tackling the hills of Siena. I am SO glad I saw Siena cathedral, but wish it had been the first stop, when we had more energy. The guide was very good, but our first, comfortable bus developed issues and was traded for a not very comfortable smaller vehicle. All in all, a good tour, but could have been great with a few tweaks.

  • 02-Dec-2019

    Really long day and we felt we could have skipped Monteriggione (very sleepy town - but could be due to low season). Tour was well organized and the guide (Sara) was very nice and pointed out sights to see. Facilitated tour at winery and lunch was lovely. Tour guide in Siena was very funny and engaging.

  • 04-Nov-2019

    Other than finding the pick up area hidden behind the train station the experience was great. Our multi-lingual guide was informative and kept us up to speed on what to expect. Plenty of time to look around and shop if you wanted.

  • 28-Oct-2019

    Overall this tour is good, we were just in Siena a bit too long for my liking. The wine tasting is simple and the product is delicious and host was funny and engaging.

  • 17-Sep-2019

    The best way to see some of the most wonderful sights in Tuscany. The relaxation of the motor coach versus the stress of driving or train transfers was well worth the cost.

  • 09-Sep-2019

    Great to see all these places in a day although it was long. Make sure you know exactly where the tour leaves from as signage is poor.

  • 26-Aug-2019

    Tour guide friendly and professional.

    Saw some beautiful Tuscan buildings and countryside. Sienna city guide Paul was good and also sense of humour.

    Would like to have spent slightly longer at each place, but as day trip time is limited.

    Would recommend.

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