in Piazza Il Campo, 1, Piazza del Duomo, Piazza Duomo, 2, Florence, Florens, Italien

Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from Florence

Piazza Il Campo, 1, Piazza del Duomo, Piazza Duomo, 2, Florence, Florens, Italien

76.24 USD

1 - 15

10 hrs 30 mins

From $76.24 USD
per person

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Tour Information

  • A full day tour, taking in the key beauties of Central Tuscany including a delicious Tuscan lunch. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

  • Around:
    • Piazza Il Campo, 1
    • Piazza del Duomo
    • Piazza Duomo, 2
    • Florence, Florens, Italien
  • Pickup: Piazzale Montelungo, Firenze FI, Italy

  • Historical & Heritage Tours
  • Day Trips
  • Wine Tasting & Winery Tours
  • Nature & Wildlife
  • Full-day Tours
  • Bus & Minivan Tours

Time of Tour
  • Departure at: 8:45 AM
  • Duration: 10 hrs 30 mins

  • Price per person: $76.24
  • Size: 1 - 15 people
  • Discount: 0%
  • Languages: English - Guide

  • Journey by fully-fitted GT Coach.
    Expert multilingual escort.
    Siena tour with professional guide.
    Light lunch in a cozy restaurant in Siena.
    Visit to a rustic wine estate in the Chianti area with wine tasting.
    Sampling of wines, extra-virgin olive oil and regional products.
    Free visit of San Gimignano and Monteriggioni.
    Entry/Admission - Chianti Road

  • Gratuities.
    Hotel pickup and drop-off.
    Siena Cathedral tickets

  • For a full refund, cancel at least 24 hours in advance of the start date of the experience

Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from Florence

Stop At: Florence, Florence, Tuscany

There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.

Duration: 1 hour

Stop At: Monteriggioni, Monteriggioni, Tuscany

You will have one hour of free time to explore Monteriggioni, Tuscany's hidden gem. This town is encompassed by its stunning, medieval walls. The town itself is so well preserved, you will feel as though you have travelled back in time to the Renaissance era... Explore the small cobblestone alleyways, take in the lovely views, and enjoy a cappuccino in the essence of historic Tuscany.

Duration: 1 hour

Stop At: Siena, Siena, Tuscany

Next, you will head to a truly unique, medieval city in Tuscany - Siena! The drive will take about thirty minutes, and then your guide will lead you through the picturesque, ancient streets in the heart of the city until you reach Piazza del Campo. In the largest square of the city, you will meet a local and professional city guide for your included walking tour of Siena. For about an hour, the guide will share fascinating facts about this incredible city (which is listed as a UNESCO World Heritage Site), and you will visit some of the most famous points of interest. The end of the walking tour will lead you to the Siena Cathedral, where you can enter at your own expense to see the breathtaking decorations and unique architecture.

Duration: 3 hours

Stop At: Piazza del Campo, 53100, Siena Italy

Your walking tour will begin in Piazza del Campo, a fascinating, oval-shaped piazza in the center of Siena. Not only is this a popular spot for locals to meet up with friends and relax, but it is also home to a historic palio horse race! Every year, the different neighborhoods of Siena join for the epic and exciting horse race. Your guide will share plenty of local stories as you walk throughout the Piazza and see some of the famous monuments. Your professional guide will share information in a way which brings the history of the city to life, in a vivid, storytelling manner.

Duration: 15 minutes

Stop At: Duomo di Siena, Piazza del Duomo 8, 53100, Siena Italy

Your walking tour ends in front of the iconic Duomo of Siena. This absolutely stunning piece of architecture is equally as beautiful inside as outside; if you would like to enter the cathedral, you will have some free time to do so (ticket is not included). If you prefer to explore the city in your free time after the walking tour, there will be some time for independent sightseeing.
Lunch will be served in a nearby restaurant.

Duration: 15 minutes

Stop At: San Gimignano, San Gimignano, Tuscany

Your journey through Tuscany will continue to San Gimignano, known as the "town of towers," because of its fascinating medieval towers still perfectly intact. The drive will take about an hour, and you will see the stunning "medieval skyscrapers" from a distance as your bus pulls into the historic town. Your guide will lead you past an incredible panoramic viewpoint of the Tuscan hills, then through the ancient city doors. You will have an hour to independently explore the town - walk the picturesque alleyways, visit the Duomo, or climb the tallest tower!

Duration: 1 hour

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

As you walk through the characteristic alleyways of San Gimignano, you will inevitably make your way to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and iconic medieval architecture! Grab a homemade gelato and enjoy the lovely views of this perfectly preserved city.

Duration: 30 minutes

Stop At: Chianti Road, Italy

After exploring these medieval Tuscan cities, you will undoubtedly be ready for some Tuscan wine! Meet back with your group, and head to a nearby wine estate in the countryside outside of San Gimignano. In about fifteen minutes, you will arrive at this characteristic wine estate, where you will be seated in a modern and beautiful tasting room built into the cellar. Enjoy the delicious wine produced at the estate: during the wine tasting, the wine producer will share the secrets of Chianti wine production with your group. At the end of the wine tasting, you will have the opportunity to purchase bottles as a high-quality souvenir of your incredible day in Tuscany!

Duration: 2 hours

Stop At: Florence, Florence, Tuscany

End your journey through Tuscany with unforgettable views of the Tuscan hills as the sunsets. The drive will take about an hour, and you will arrive in Florence in early evening.

Duration: 1 hour

Sample Menu

• Cheese, bruschette and cold cuts
• Pasta with bolognese sauce or tomato sauce
• Typical Tuscan biscuits

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Additional Information

Confirmation will be received at time of booking.
Not wheelchair accessible.
A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements.
May be operated by a multi-lingual guide.
English and Spanish languages are always guaranteed. In order to confirm the excursion in French, German, Italian or Portuguese a minimum of 4 pax is required.
Stroller accessible.
Service animals allowed.
Near public transportation.
Infants must sit on laps.
Infant seats available.
No heart problems or other serious medical conditions.
Please note that the given order of the visits may change.
Please inform us of any food intolerance or allergy in advance.
Travelers should have a moderate physical fitness level.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
This tour/activity will have a maximum of 30 travelers.
Face masks required for travelers in public areas.
Face masks required for guides in public areas.
Hand sanitizer available to travelers and staff.
Gear/equipment sanitized between use.
Transportation vehicles regularly sanitized.
Regular temperature checks for staff.
Temperature checks for travelers upon arrival.
- A safe distance of one meter between clients will be maintained whenever possible. - The use of masks is mandatory. Clients must bring their own mask. - Showing your voucher on your phone will be enough; it is not necessary to print anything.


5.0 stars, based on 36 reviews

We're glad we booked this daytrip outside Florence as it's become one of the highlights of our trip!!!! We originally booked for the tour including Monteriggioni but due to guest numbers, we agreed to do the tour that included Pisa instead.

Lots of free time to take pictures, eat, get espresso, and gelato. Our guide throughout the trip Frankie was friendly, funny, and shared information about Tuscany during the bus ride. But he also gave us time to nap which was very convenient and considerate - the whole trip is really a full day! Shout out to our driver Raul too who's a super cool rockstar! Highly recommend this trip - San Gimignano was beautiful! Get the gelato from Dondoli it's so, so good! Lunch was also amazing, simple but delicious, including three wines. The views overlooked vineyards and wineries so it doesn't disappoint!!!


The tour was great. We had enough time at every stop and the wine tasting at the end was also a very nice experience! Our tour guide Marco was very passionate and helpfull throughout the tour. He was a really good guy with a lot of infos.
Our driver Sergio was also very good and drove safely all the time. All in all a very nice Trip and worth the Money. Because of corona we also just were 20 people on the trip what was nice too! Really recommend.


Really great tour of the surrounding Tuscan areas from Florence. Francesco was a top notch guide for the day, and the wine tasting was a surprisingly good highlight!


It was a lovely day from start to finish are guide was brilliant the three stops were all good the wine tasting was my favourite it was so pretty wine and snacks were out of this world and the guy telling us about the vineyard give us loads of information and even delivering the wine and oils to are house couldn’t have asked for more


This trip was amazing and definitely worth the money. Not only did we see 3 beautiful UNESCO villages we finished with a lovely wine tasting. It was our guide, Constantine’s first tour since Covid-19 lock down and he was amazing. He was so informative and even went out of his way to show us highlights of the villages. You could tell he was genuinely excited to share his knowledge. The lunch was plentiful and delicious. A fantastic day in Tuscany.


Great trip even though the weather is not good. We covered three city/towns alone the way and a very enjoyable wine tasting. We were thinking about a private tour for double the cost. We are very happy to join the group tour and made few friends alone the way.
Tour guide and driver are great and same as the group member, we waited few minutes for one couple and event less the rest of the way.
Highly recommended. Especially for the first time. If you really like the region, you can always spend more time later. For starter, it is a very good introduction.

Barbara H
Barbara H

My family and I thoroughly enjoyed our tour. It is a full day tour with lots packed in - a great way of getting lots done on limited time. Our guide for the day was lovely, full of knowledge and interesting facts yet also gave you space throughout the day.
I found I had plenty of time at each stop off except for siena but that’s because there was just too much to see and do, just means I’ll have to return!
The wine tour was a nice change in pace, please don’t expect a full on vineyard tour but more of a taster - perfect for us who had children.

Isla G
Isla G

Ava our guide was lovely and very helpful. The trip to Sienna was a highlight for us as they were setting up for their annual horse race. The wine tasting was a perfect end to a lovely day.

Rhonda M
Rhonda M

We started the day early visiting San Gimignano before the crowds. Good lunch at Sienna. Very enjoyable tour guide Marco. Good way to visit no hassles.

Richard M
Richard M

I was very impressed with our tour overall! Frederica was such a knowledgeable tour guide translating into three languages flawlessly (as far as I know) and none of them were her native tongue! I was a little disappointed with the winery tour. I have been on tours of beer factories and distilleries and am used to seeing some of the process and touring the grounds. I thought for sure we would be ambling through some olive groves or vineyards, maybe seeing some grapes or olives squashed. Nonetheless, the rest of the tour was amazing and very informative. There was plenty to see and do, and the tasting was fantastic. I bought several bottles of this and that to be sent home. The winery gave me a lovely little wine tool as a souvenir which was confiscated at Customs upon reaching the US. Still, the memories of the tour of these wonderful places remains.

Argenteam Marina
Argenteam Marina

this trip was very interesting and enjoyable. The guides are very attentive and have good historical knowledge of the area. but it would have been useful to warn that in some establishments they do not accept the card or if they accept only for values ​​above 10 euros. the guide in siena who spoke in Spanish explained clearly in Spanish and was very knowledgeable. for who is Brazilian to understand perfectly. a pity the visit in siena to have been run, would need more time to know the works of the duomo. the visit to the Echianti vineyard could be last, since we were still digesting our lunch.

Steven A
Steven A

We had a great time on this tour and enjoyed all of the destinations. We would have enjoyed a little more time in the different locations but we understand that is not practical with so many things in one tour. The only thing that might have allowed us to spend more time would be to limit translations to one or two languages (it was a bit long waiting for every spoken word by tour guides and others to be translated 3 times).


Great tour. Loved seeing the hilltop towns, excellent lunch and trip to a winery. Perfect experience in Italy. Bus, tour guide and driver were excellent! Highly recommended.

vanessa c
vanessa c

This tour was an amazing day tour, we got to discover this little village called Monteriggioni, then we went to Siena, which I found to be the most amazing city its history was mind blowing. From there we went to a winery had a wine tasting and then went to San Gimignano, a small town full of charm and breathtaking views. I recommend this day tour it was great!

Malcolm L
Malcolm L

We enjoyed the cities visited and their history and sights. Lunch was really good and the visit to the winery capped a wonderful day.

maria m
maria m

Siena was a very nice city. I loved that old town of San Gimignano and Monterriggioni. The Gabriel, the guide, was incredible. I enjoyed this tour a lot.

Neil D
Neil D

This is a must tour when in Florence. Although the group was a full bus load, our guide Chiara was able to take the lead and was very informative of the history of the areas we visited. There was a group of us that bonded which made it quite enjoyable. Having some great wine at the finish of the tour was a nice way to end the day. The wine was excellentalthough expensive, I ended up purchasing 2 bottles.


This tour was great! They take you to some of the most beautiful places in Tuscany. I would’ve loved more time in Siena and San Gimignano because they are just so beautiful but for a one day tour I think they do the best with the timing. The tour guides were really warm and friendly and made the day very easy going. Lunch was simple but delicious! And the wine tasting part was fantastic!!! I would definitely recommend this tour if you don’t have the time to visit these places on your own!

Aerin K
Aerin K

Absolutely, yes!!!

Lia G
Lia G

This was another highlight of our trip. We got to see so many towns and sights in one day without having to drive. Everything was seamless and the tour was great. There was enough time to get to see each place with our allotted tour time and the wine tasting tour was amazing. An unforgettable Tuscan experience and definitely worth the price.

Ann M
Ann M

This tour is the best way to see all of the Tuscan countryside. Every single stop had so much to do and the tour went by so fast since there was so much to do. It is a lot of walking up and down steep parts of the town. The tour guides were so accommodating and so helpful with anything we needed. The included lunch was AMAZING. We had a lovely time getting to know others on our tour! The wine tasting was the best treat we didn’t expect to get. You are put in a lovely room and taste four glasses of wine along with truffle butter and balsamic. This tour was worth every single euro and I would do the tour 20 more times if I could.


The train station was easy to navigate for pick up/drop off. The tour was great for a group that size. We got our own food in Siena which we were glad we broke from the group for a bit. The winery was a blast. San Gimignano had stunning views. Monteriggioni was a fantastic start to the day.


We are a family group of 4 adults and 3 children (14,12,8).
I looked into getting a private guided tour of Tuscany but found it quite expensive. This tour was great value and covered most of what we wanted to see. Lunch and winery - both great.
Good value and comprehensive tour. Guides were great

Kris P
Kris P

Great tour. Beautiful scenery. Good value.


Excellent guide, safe, professional driver and the tours were first rate. Beautiful towns and Sienna was very interesting.


Tour was great! Long day, but lots of cool stops. Especially enjoyed Sienna, a hidden gem not far from Florence. Perfect trip to do if you are spending multiple days in Florence and looking to explore the surrounding region and get a little taste of Tuscany.

Dr. Ian C
Dr. Ian C

A wonderful day trip. Excellent guide throughout and lovely views of the Tuscan countryside. San Gimigniano is spectacular and there is adequate time there to explore a little. Time in Siena which included an excellentlunch a bit rushed. The wine tasting was fun and a nice end to the day.Monteriggioni was interesting but could have been missed in favour of more time in Siena.
A previous trip to San Gimigniano and Siena only was better balanced and gave more time in each. All the same this was an excellent tour and highly recommended


Well-organized full day tour. The Siena dome is a wonderful experience, a heigth of this journey - don't miss it!


This was in Feb.on a cold rainy day. The driver was great driving in this weather to each place. Our guide was friendly and spoke in different languages for all to understand.
He was good at explaining the history of where we were going.
The Siena restaurant we had lunch was delicious! Very nice.

Kerry D
Kerry D

This was a great way to see parts of Tuscany that we otherwise wouldn't have been able to.

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