Private Tuscany Tour: Siena, San Gimignano and Chianti Day Trip

Recommended by 98% of travelers

Badge of Excellence

Florence, Italy

8 hours (approx.)
Pickup offered
Mobile ticket
Offered in: English

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Overview

The best way to see the Tuscan countryside is by car, but renting a vehicle means you have to keep your eyes on the road, instead of on the area’s bucolic beauty. Leave the driving to someone else when you head out on a private excursion to Siena and San Gimignano. Going with a guide also means you learn more about the area than you would on your own.

A perfect introduction to Tuscany for first-time visitors
Leave the driving to someone else when you go with a guide
Round-trip transportation from your hotel maximizes convenience
A private tour ensures personal attention and flexibility

What's Included

Driver
Hotel pickup and drop-off
Private tour
Transport by air-conditioned minivan

Food and drinks

Meeting and Pickup

Pickup points

Select a pickup point

Operating hours
.9:00 am

Itinerary

Piazzale Michelangelo

10 minutes • Admission Ticket Free

Il Campo, 1

1 hour 30 minutes • Admission Ticket Free

San Gimignano

1 hour • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Stroller accessible
Near public transportation

Infant seats available
Most travelers can participate
This is a private tour/activity. Only your group will participate

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Renee_S

Simone our guide was fabulous! She took us local places that visitors would not know about. She took us to a beautiful Memorial that would take your breath away. Her knowledge of the region was great. We vitiated a couple wonderful wineries and had a three course lunch that was phenomenal! Thank you

Reviews

4.9

based on 64 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Great day in Tuscany!

Georgia_N, Nov 2025

Marco was amazing. He is a local and very knowledgeable and friendly! (He is also the owner of the company!) We had a great trip to Siena and San Gimignano. He's flexible and easy going. He was able to give us the history and recommendations on where to go in each town. I HIGHLY recommend Marco and his company!

Beautiful

Megan_M, Mar 2025

It was fantastic!!! Marco and his partner were wonderful. He was knowledgeable and patient with us all.

A magical day in Tuscany

Laurie_T, Mar 2025

This was a well paced, customized tour that offered a perfect blend of narrated tour and independent exploration. We loved Michelangelo Square for its view of Florence, San Gimignano, San Reggimiento, the Florence American cemetery honoring 4,000 American soldiers lost in WWII and the special photo stops we hit along the way. Marco, our driver and host, set up an extra special winery visit to the Il Columbaio winery. We enjoyed (and ordered!) some excellent wines and had salamis, cheese and pasta. Highly recommend this tour - all 6 of USA loved it!

Phenomenal

Renee_S, Oct 2024

A little bit of heaven

Neil_S, Oct 2024

Marco was very, pleasant, helpful and knowledgeable. The wine tasting and lunch at San Appian winery is not to be missed.

Customer Service at it's Finest!

Tanya_V, Jul 2024

This was one of the best parts of our two week Italy vacation! Our tour guide, Sam, provided first class service & made our trip personal, memorable, and relaxing. He was very accommodating & modified the excursion by granting our request to avoid crowds of people & drive through the quiet Tuscany country instead. We definitely recommend adding the option for a winery lunch & tasting. In addition, communication with the tour operator through Viator was very easy. They confirmed that the tour would be able to transport my Mom's collapsible wheelchair, and they did! Thank-you so much for this amazing experience.

Wonderful day trip

Nancy_N, Jun 2024

We had a very enjoyable day with Marco. He picked us up at our VRBO. His van was comfortable for our family of 6 adults and very clean. He had water for us. We first stopped in Siena. There was a line to get tickets to the Duomo and the panoramic fortress (I would advise to get in line quickly or buy online before). The views were well worth it. We also had time to walk down to the piazza del Campo, which was also spectacular. We opted for the winery lunch and it was fabulous. We tried about 6 wines and had a 4 course Tuscan lunch that was delicious. We then went to San Gimignano and walked about the walled city, enjoying the shops and gelato. Marco shared stories of the area's history and made the day so enjoyable for our family. Highly recommend this day trip from Florence.

Excellent Service!

Kristen_C, Sep 2023

Marco was great! On time, friendly, informative, and went out of his way to ensure my mom (who has some mobility issues) was comfortable in Siena. Would highly recommend.

Perfect day in Tuscany

Jennifer_D, Aug 2023

Absolutely the BEST day ever! We loved having the flexibility to visit each town while also going at our own pace! The lunch at the winery was splendid and so personal! We felt like family! Marco was the greatest driver and so fun to get to know!!! One of our favorite tours we did in Italy!!!

Favourite part of the trip!

alexchurchill, Jun 2023

Marco was amazing to deal with from the start. He was incredibly responsive to any and all inquiries we had about what we would experience on the tour. On the morning of the tour Marco promptly picked us up at 9am at the front door of our AirBNB. From there he took us to San Gimignano where we were given around one hour to walk around on our own. He was very accommodating with the pick up and drop off points at each location and provided some insights on things we should check out. From San Gimignano we were taken to a small winery (Sant’ Appiano) where we were given a short tour and then sat outside for a wine tasting and lunch. This was one of the most memorable parts of our trip and is worth the extra 60€ (which was paid in cash at the winery). Lastly we were taken to Siena where we had about and hour and a half. We found the time allotted in each location to be sufficient and not overly rushed. I would highly recommend this tour and Marco, and will certainly reach out to Marco again in the future for a tour if we are in the area.

Best way to see Siena/San Gimignano in a day

caciaverelli, Jun 2023

This is absolutely the best and most efficient way to see these cities in a short period of time. Marco, our driver, was incredibly helpful from picking us up outside our AirBnB and dropping us off literally at the gates to Siena and San Gimignano, to making a lunch reservation for us at an awesome restaurant, to giving us tips on how and what to see in a limited timeframe. Marco was professional and kind. He took a slight detour at the end of our day also so we could see the most amazing view of Florence from the Pizalle Michaelangelo. If you have anyone in your group who has mobility issues, or simply want to use your time the most efficiently definitely book this tour!

Response from Host, Jun 2023

Hi Carrie! Thanks for this wonderful review! It' s been a pleasure to take care of you and your adorable family and show you how beautiful is Tuscany. I' d love to be again your driver in the future and drive you to visit other nice places in Tuscany. My warmest regards, Marco

Fabulous tour of the countryside

Dee, Apr 2023

Marco was an amazing tour guide. We saw incredible views and at his recommendation, had an amazing lunch in a winery with wine pairings. A highlight in our Florence vacation!

Response from Host, Apr 2023

Hi Dee! Thanks for your nice words about this tour through Tuscany with my company. It was a real pleasure driving for you and your party. I hope to see all of you again in the future for other wine tours in my region. My warmest regards, Marco Modesti

Do not miss!

Heather_W, Apr 2023

What a special day! We got picked up at the hotel and lavashly taken to an ama I g spot to see the whole city from up high. Then we went to San Gimignano for a bit of shopping and the sites of this beautiful city. Then to an amazing lunch and wine tasting at St. Appiano winery where they showed us how and where they produce their wine followed by lunch and tasting in the cave where they age their beautiful wines. Then off to Sienna for more medieval city and then back to our hotel. It was educational and so relaxing! I highly recommend!

Fantastic day trip from Florence to Siena and San Gimignano!

rafinazarians, Oct 2022

We took a day trip from Florence to Siena and San Gimignano with a stop at the highest point of Florence to see a replica of the Michelangelo and breathtaking views of Florence. This was an excellent trip that we would highly recommend. Our driver and tour guide Marco picked us up from our hotel exactly on time and we were on our way. Marco was absolutely charming and and shared so much information and interesting facts along the way. We went to Siena first and had about an hour and a half to explore the city. We then went to a lovely winery for lunch and wine tasting and then we went to San Gimignano for about hour. Both cities and the winery were picturesque and so much fun to explore. We then drove back to Florence and made a quick stop at the highest point in the city. Marco was fantastic. Do yourself a favor and take this tour. 10 out 10!

It was a great day, our...

Linda_W, Oct 2022

It was a great day, our driver was very knowledgeable! In hind side, the time in the cities was a-little rushed so next time I would fore go the lunch at the winery and split the time in the two cities. But overall very special day!

Response from Host, Oct 2022

Hi Linda, Thank you very much for your nice words about this private tour that you had with my company and I' ll be very glad to take care of you, next time, if You will book again through my company. Anyway, I just wanted to specify to the audience that, as very well explained in this tour page, we stop 1 hour and half in Siena and 1 hour in Sangimignano and this is what' s the expectation about the stops in the 2 cities. But since we are very flexible, on customer' s demand, we can also get the stops in the 2 cities longer of course. When the customers don' t show the will to stay longer in the cities, we always rispect the tour schedule displaied on its viator page. My warmest regards, Marco Modesti

Exceptional tour!

Rebecca_B, Jul 2022

Exceptional tour through Tuscany. Both towns were amazing to visit-the age & history of each was incredible. Lunch at a small country winery was very enjoyable & well done. We would highly recommend this tour to anyone visiting this area.

Sienna, San Gimignano, and Winery Visit

Karen_S, Oct 2021

Our tour from Florence to Sienna and San Gimignano was a highlight of our trip to Italy. Tommaso is an excellent tour guide and driver. He is friendly, knowledgeable, and patient…stopping to take photos and provide background at a number of scenic locations. He shared stories about growing up in Florence and made us feel comfortable and welcome. We had plenty of time to walk around the cities and do some shopping. The best part of the day was a stop at a small winery, Podere La Marronaia, for lunch with wine and olive oil tastings. We enjoyed the the food, the wines and the beautiful setting. We would highly recommend this tour. Viator was easy to work with, and our family had a memorable day. Thank you, Tommaso!

Tuscany

Corey M, Nov 2019

We had excellent time with Marco! He was very knowledgable and knew where to take us. We would highly recommend him and using Viator was very easy. thanks! Corey - Dallas

What an incredible tour!

Emily_K, Sep 2019

What a great day! Marco was an incredible driver and tour guide. This private tour allowed us to make some decisions about what we wanted to do for lunch, we decided to stop at a vineyard outside of San Gimignano and it was the best 3 hours we spent that day. The wine and food was delicious! We had plenty of time in Siena and San Gimignano to get some shopping done and see the city. Would highly recommend this tour!

Martino was an excellent guide. He...

Shamitri_P, Jul 2018

Martino was an excellent guide. He was a safe driver, well-versed in all things Tuscan and just really pleasant. Anything I asked him, he was able to explain to us. I did most of the asking because I simply love the Tuscan countryside and cannot get enough. We were a family of 4 and we splurged a bit on this tour. So glad we did because it was so much fun for my teens and comfortable as well. Siena was lovely, they were getting ready for the Palio, so it was an experience for us. When you stroll around, there are some great areas for picture taking. Not over crowded like I expected. Lovely shops, I found an amazing hand-made linen table runner, just love it. Martino picked us up when we were done, we were relaxed and happy. Next he took us to a winery for lunch. What an amazing experience it was. We spent way too much time, without even realizing how long. Met others traveling from America, talked, did a tour, their wines are so good, 6 tastings and food to pair with the wine, Lorenzo was our guy, he was so good at explaining what we were tasting, the sangiovese, the chianti reserva and classico which they are famous for and very proud of the fact that they aren't mass produced which I really liked. The cheese was divine! Their vegetable garden was delightful.Our backdrop was the gorgeous Tuscan countryside, who wouldn't want to eat, drink and relax with a view like that. We loved it. San Gimignano was just as lovely but much quicker because we were drinking all that wine, we did not mind. Our pace however wasn't rushed and Martino took us to a place so we could take photos as well. Completely worth while. Thank you! Marco for responding to me! Martino was simply fabulous.

We really enjoyed our tour with...

Morgan_M, Jun 2018

We really enjoyed our tour with Martin! He arrived on time, and was pleasant to talk to. He knew a lot about the region. The van was roomy and comfortable. We really enjoyed walking through both San Gimignano and Siena- great shopping in both cities. He took us to a small family owned winery and restaurant in Chianti Fattoria SantAppiano for lunch, which we loved! Had a fantastic homemade meal. We even liked the wine so much, we got some shipped to us. We also appreciated his flexibility, as we requested that we bring our luggage along with us and we get dropped off at our next resort outside of Siena. He was accommodating to all requests we had. It was a great day!

We booked this tour two days before...

Susan A, Mar 2018

We booked this tour two days before and it was the best part of our trip to Italy. Our driver, Marco, was excellent and really went out of his way to accommodate our needs. I would highly recommend this tour if you want to see the beauty of Italy without the hassle of trying to keep up with a large tour group!

THIS WAS ONE OF OUR MOST AMAZING...

Donna H, Oct 2017

THIS WAS ONE OF OUR MOST AMAZING DAYS IN ITALY!!!!! We are four friends 40s-50s. We initially considered doing this trip as a group tour, but decided to pay a little extra for the private experience. WELL WORTH EVERY PENNY!!!! We were picked up by our private driver, Marco, who was ABSOLUTELY WONDERFUL!!! He picked us up at our airbnb in Florence. He was prompt, polite, efficient and couldn't do enough to make sure we had a super day. We first went to Sienna. We loved all these medieval towns! Totally cool place to visit. Then we went to the La Podere Marronaia Winery for the lunch experience. We walked in and I heard all the noisy group tours eating their lunch on the lower levels. Marco whisked us away from the noisy crowds and took us upstairs to a sort of penthouse room. We had a private room with a table set for us with open farmhouse windows on the most beautiful day with breathtaking views of San Gimignano and the Vineyard. Once we were in the private room, we couldn't have been happier that we upgraded to the private experience. It was 40 euros per person for the lunch and wine/olive oil/balsamic vinegar tastings. The food was delicious bruschetta of different flavors, cured meats and olives, pasta and TONS OF WINE!!!! Everything was just scrumptious. We were served biscotti with dessert wine afterwards. We had the most wonderful waiter, Corrado, and he introduced us to his beautiful mother, Sylvia. We all left feeling like old friends and we ordered many goodies which would ship to the US for free. It was quite an experience for 40 euros a piece. When lunch had ended, Marco took us to San Gimignano, which was another cool town. We just loved everything about this experience -- our awesome driver, Marco, the cool towns of Siena and San Gimignano and the upgraded experience at the winery. WE HIGHLY RECOMMEND THIS TOUR!!! YOU WON'T REGRET IT

Great day in Tuscany! Paolo was so...

Dorri K, Mar 2017

Great day in Tuscany! Paolo was so knowledgable gave us a whole history of the area as we were driving. Extremely accommodating, as our plans kept changing about which areas we wanted to visit. Mercedes Van, very comfortable . Highly recommend !

Best tour ever!! Marco was amazing...

Shelley S, Jun 2016

Best tour ever!! Marco was amazing and totally treated us like royalty! We had the best lunch at Marronaia!! Thank you!!

Great to leave the hustle and bustle...

amscooks, Nov 2015

Great to leave the hustle and bustle of Florence and have a quiet day in Seina and San Gimignano complete with an optional stop at a local winery. We had a wine tasting and a delicious lunch. Marco, our driver, was informative and a pleasure to spend te day with. Worth every penny!

Private tour was very flexible in...

Alfred N, Nov 2015

Private tour was very flexible in changing itinerary. Left later at 2:00pm instead of 9am and was able to visit San Gimignano first followed by Siena. This allowed us to have dinner at Siena. Our guide / driver was Marco who was very helpful and great throughout the tour.