San Gimignano, Siena, Monteriggioni, Chianti: Day Trip with Wine & Food Tasting
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San Gimignano, Siena, Monteriggioni, Chianti: Day Trip with Wine & Food Tasting
/ Italy / Tuscany / Metropolitan City of Florence / Florence / Tours & Activities /
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San Gimignano, Siena, Monteriggioni, Chianti: Day Trip with Wine & Food Tasting

1 day
Full Day
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About this activity
This is a typical itinerary for this product

Stop At: Historic Centre of San Gimignano, Piazza del Duomo 2, 53037, San Gimignano Italy

Chianti Hill Top medieval Village, famous also for its towers

Duration: 1 hour

Stop At: Piazza del Campo, 53100, Siena Italy

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, Piazza del Campo, Siena Italy

The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race. The Museum of a ”Contrada”, as well as its Oratory, is therefore 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 It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art, which are normally not disclosed to the public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, Piazza del Duomo 8, 53100, Siena Italy

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: Piazza Roma 15 Castello di Monteriggioni, 53035, Monteriggioni Italy

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, Italy

Then crossing the gently Chianti rolling hills, we will arrive to a cozy Winery, where taste four fantastic wines and sampling balsamic vinegar and “zero food miles” products , to end this memorable experience in the heart of Tuscany with delicious Tuscan flavors

Duration: 1 hour

Stop At: Piazza della Cisterna, Piazza Della Cisterna, San Gimignano Italy

Not-to be missed during your free time in San Gimignano

Duration: 5 minutes

Stop At: San Gimignano Bell Tower, Piazza del Duomo, 53037, San Gimignano Italy

Not-to-be-missed during your free time in San Gimignano

Duration: 5 minutes

Stop At: Banca Monte dei Paschi di Siena, Piazza Salimbeni 3, 53100, Siena Italy

external visit not-to-be-missed during your free time in Siena

Duration: 5 minutes

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  • Transport by G.T. air-conditioned vehicle with WIFI on board
  • Licensed Tour escort with live commentary on board
  • Shared or Private Professional guide in Siena (depending on the selected option)
  • Guided visit in Contrada's Museum and Oratorio
  • Stop at a typical Winery with tasting of excellent Chianti wines and typical products
  • Visit of a picturesque Chianti medieval village, famous for its colors and charm
  • Siena Cathedral interior Guided Visit including entrance fee (depending on the selected option)
  • STARTING FROM NOVEMBER 2019: New Tour edition with Lunch included
Not included
  • Entry/Admission - Duomo di Siena
  • Confirmation will be received at time of booking
  • STARTING FROM NOVEMBER 2019: New Tour Edition with Lunch included
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • A 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.
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 50 travelers
Joseph I
5 | 2019-09-17

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.

4 | 2019-09-09

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.

James S
4 | 2019-08-26

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.

Sheryl Fernando
4 | 2019-08-12

San Gimignano and Sienna were the highlights of this trip. Monteriggioni was not worth the stop in my opinion but the wine tasting was well organized and a nice way to end the day. Overall , a great tour !

5 | 2019-07-24

Our group was not disappointed with this tour. The guides were outstanding and the pace of the day was quite reasonable.

David S
3 | 2019-07-03

We took this trip recently while staying in Florence. We enjoyed our trip although we did have a couple of issues which future customers need to note. We have to say our guide Donnatella was helpful on the coach speaking in more than one language and informing us of places en route. Our coach was also comfortable although my husbands seat was broken as was our guides seat. We enjoyed seeing San Gimignano which is very pretty with alovely church we visited there. There are many gifts shops here but it still remains charming. We did have promlems with Sienna though as we had booked an optional visit to the cathedral there which our tour guide seemed to have no knowledge of. She quickly got on her phone and seemed to have a heated conversation with someone when it was pointed out. This didnt give us much confidence in the trip we had pre booked before coming to Italy! When we arrived at Sienna we felt we had to rush to keep up with our guide and if we had not been intent on following her we didnt feel she would have noticed our absence, the whole trip was very rushed with under an hour to get lunch in a busy square, we bought a baguette from a baker knowing we wouldnt have time to order food after the slow experiences we had had before with ordering and paying, all too stressful! The whole experience of Sienna felt very rushed. Donatella was sharpe with us when we asked about our cathedral visit and seemed stressed most of the time. It was now lunchtime and we still had no info about our cathedral visit. The information about the Palio contrada was far too much in depth and other people looked bored with the time spent on it. We were given another guide for this...we asked her about our cathedral visit....she replied...this is a group tour and not a private tour, when we realised we had just 30 mins left to meet Donatella and little time to see the wonderful cathedral. We ended up with about 20 minutes in the cathedral with the guide and wished we had not taken this extra visit, which was really rushed. We then had a whisle stop walking tour back to our coach literally running after Donatella back to the coach, which other guests commented on! The wine tasting was very good and relaxed with a fun host, although beware, the goods are expensive to purchase. All in all too much was squeezed into the trip, communication in this company clearly lacking... we had a nice day which was highlighted by stress, our advice, dont book the cathedral...which was beautiful .

4 | 2019-07-03

We enjoyed the tour, however, we signed up for the English tour, but they also did French and Spanish which was pretty annoying. I would have given it 5 stars if not for that.

Robert I
4 | 2019-07-03

We enjoyed the tour knowing in advance that it’s fast paced (group moves quickly/short visits) no frills (no bottle water, no bathroom on bus, no lunch) and multi language (many languages, much translation time). But you get some great stops in beautiful places with a tour guide that provides some helpful commentary. You get fantastic Tuscan scenery that makes the short drives between stops very interesting and enjoyable. A full day (almost 11 hours) you want to go prepared for!

Bryan W
5 | 2019-07-03

Made a choice to drop pisa from the itinerary and go for this tour instead. Did not regret it. Wine tasting session was very informative and generous. Opt for the tour of Siena. you do not want to miss out on learning about the town's rich culture and history.

Hayley N
4 | 2019-01-31

We went on this tour in January and had such a lovely day! The meeting point was very easy to find as it is the main bus stop of the town, and when we got there our tour company was easily signposted. The group was small which made it easy to organise everyone and minimised waiting times. All of the stops were perfect length and allowed us to enjoy free time. The driver even stopped off at the Michelangelo's Square on the way at 8.30 in the morning, allowing us to see some beautiful views as the sun was coming up! The wine tasting ended the day perfectly, trying 3 different wines as well as delicious olive oil, balsamic vinegar and cheese. The only thing I would mention is that we paid for the Siena Cathedral tickets and weren't given these until 10 minutes before the bus was due to leave, giving us very limited time to explore the Cathedral despite asking the driver about this numerous times when we first arrived. The tour guide was great - very enthusiastic and informative.Overall an amazing day! Would definitely recommend and I look forward to going on another tour with them in the future :)

Susan C
5 | 2018-10-22

The day in Tuscany at the different towns was beautiful and interesting. We met some great people on board and the guides, especially our local guide in Siena, was terrific. We would highly recommend this tour....great value and different experiences made for a full day.

3 | 2018-10-08

Overall, it was a good trip. I wish we could have eliminated the castle tour and spent that time in San Gimignano. Otherwise, good tour.

5 | 2018-09-26

Great trip from Florence to see some nearby cities and great sites! Siena and wine tasting were the highlight!

Kristin J
5 | 2018-08-10

AMAZING!!! great tour guides especially in Siena! one of the highlights in our italy trip!

Walker H
2 | 2018-08-05

Tour was in three languages therefore not in depth. Only surface level history/attraction explanations. The highlight of the trip was the wine tasting. Our time in San Gimignano felt rushed. The city was beautiful, we would have liked to spend more time there. The tour of Siena was all based around it’s horse race.

3 | 2018-07-11

We got to the first small hilltop town. The bus drops you off but you have lots of stairs and some steeper sidewalks to climb. We only had half an hour to wander and shop which was not nearly enough time. The scenery out over the hills was stunning! Then off to Sienna. 3 hours there which was 2 hours too many. The local guide was terrible!!! She is why I didn't rate it higher. Then off to another tiny hilltop town. Again only half an hour. It was so charming I wanted to spend a couple hours there taking photos and shopping. Very disappointed in the short time there. Then a winery which was very nice. I would not do it again.

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