• Private Tour
• Carbon Neutral

Worldwide famous for its city districts, its horserace (Il Palio) and home of the second oldest bank of the world, the medieval town center of Siena is one of those jewels you cannot really miss out. Visit it with a local on a day trip that will fascinate you and take you back in time!

Destination

Florence, Italy

Category

Day Trips

Duration

6 hours

Transport mode

Car

Available languages

English, Italiano, Español

Included

• Private guide
• Driver
• A/C Car
• Pick-up Included

Excluded

• Lunch
• Admission fees

What you can expect

This is the plan

Check out the plan below to see what you'll get up to with your local host. Feel free to personalize this offer with Fabio.

1. Meeting point

   You will be picked up anywhere in Florence. Your local host will contact you regarding the exact pickup point.

2. Itinerary

   This is what our experience could look like, but it’s not set in stone! Once you book, you can chat directly with your host to make small tweaks to suit your preferences.

3. Meeting Point

   Pick up at your accommodation

4. Stop 1

   Take the scenic route to Siena

5. Stop 2

   Explore the historic city center of Siena declared by UNESCO a World Heritage Site

6. Stop 3

   Have a local lunch in the city

7. Stop 4

   Learn about the most famous Italian horserace

8. End of tour

   Drop off at your accommodation

9. Make it yours

   Want to tweak the itinerary? Book directly & chat afterwards with your host to adjust highlights, skip stops, or make small changes to fit your preferences.

   Book risk-free: Cancel within 24 hours for a full refund.

   Need something special? Personalize your experience for more time, alternative locations or a completely tailored plan.

I can personalize this tour for you

• Tell me your preferred date and group size
• Tell me your preferences and wishes so I can customize the tour for you
• Wait for my personal offer in your inbox!

Contact me

Flexible cancellation policy

• Feel confident booking

  Cancel within 24 hours for a full refund. Even up to 7 days before your experience, you’ll receive a refund, minus the service fee.

• Change of plans?

  Reschedule your experience to a date and time that works best for you.

• Loved by travelers worldwide

  Simple and flexible – your plans, your way.

Reviews from guests

Adam🇦🇺 Australia

29 June 2023

Fabio picked 7 of us up in a very comfortable car. We went to Siena from Florence and spent some time there. But the most memorable experience was having lunch and wine tasting in a Chianti vineyard. We learnt about the wines and the wine making process before sampling the wine. We had lunch and invited Fabio to join us and we shared storeys over good food and great wine. It was a great authentic Italian experience. Fabio is very knowledgeable, very engaging and great with the kids. We’ll see Fabio again on our next trip for sure. Fantastic guide and experience

Lucy🇺🇸 United States

29 July 2022

Fabio was very friendly and knowledge about Florence, the countryside and Siena! He lead a wonderful conversation and gave us a great suggestion for lunch. I also give him 10 out of 10 stars for safe driving. He navigated the city, country and narrow roads of Siena like the pro that he is!Great guide and driver!

Unknown

9 May 2022

Fabio arrived on time to our hotel, and drove my husband and me in his comfortable minivan from Florence to Siena. On the way, we had a very engaging conversation as he shared with us some history of Siena and Florence, and their historical relationship. He left us in a central meeting spot in Siena with instructions to meet back in that place after the tour. He suggested some key highlights for us to visit in Siena, and made a lunch reservation for us at a local restaurant. That lunch turned out to be the best meal we had on our trip to Tuscany —by a long shot! Just wonderful. By agreement, Fabio’s dad Luigi was actually the one who drove us back to Florence, due to Fabio having another engagement. Luigi was likewise pleasant, personable and a good driver. He didn’t speak much English but between his English and our little bit of Italian, and sometimes meeting in the middle in Spanish, plus hand gestures, we did just fine. We highly recommend Fabio —and Luigi —for tours of Tuscany. Laura Gottardi-LittellPersonable, easy-going, and knowkedgeable private tour guide

Bob 🇨🇦 Canada

2 October 2021

Fabio was friendly, informative and accommodating to our specific needs. He provided a wealth of knowledge and insight about the region and Italy as a whole. Fabio also gave recommendations on where to eat and other sights for the remainder of our trip. We enjoyed an excellent full day. We all felt that this was one of our best tours ever!Great guy with excellent knowledge

Ilse🇧🇪 Belgium

1 March 2020

We really enjoyed the trip with Fabio to Sienna. He is an excellent and very knowledgeable guide, learning us so much about Italy, Tuscany and the incredible cities of Florence and Sienna! He is a very spontaneous person, it didn't take long before we felt being on a day trip with a friend! In Sienna he explained us what we should certainly visit and at noon we enjoyed the most delicious pizza in an authentic 'consorzio agrario'. As the weather was so nice, we enjoyed spending some more time walking around together in the lovely town of Sienna, to an incredible view point. We can really recommend Fabio to everyone who wants to discover the real Tuscany!wonderful and interesting day in Tuscany

Michael

29 October 2019

Fabio was very knowledgeable about, well, everything! Very easy to talk to and was able to show us all the best of Siena and San Gimignano. 10/10 would highly recommend!Great tour and guide

Silvia 🇺🇸 United States

29 October 2019

We had the most wonderful time with Fabio as our tour guide. He was exactly what we expect from a guide; knowledgeable and respectful of our needs. He gave us enough time to enjoy each city and even arranged a wonderful lunch. I highly recommend him and will definitely book with him again.Fabulous trip to Siena/San Gimignano

Sharon 🇨🇦 Canada

10 September 2019

We had a wonderful day trip to Siena with Fabio. He was very pleasant and informative. We learned a lot about the history of Tuscany. We had a fabulous trip and would highly recommend him.Day trip

BRIDGETTE 🇺🇸 United States

14 August 2019

Fabio picked us up at our hotel in Florence. We spent the day exploring San Gimignano and driving through the gorgeous countryside. We visited a local winery for lunch and wine tasting. Fabio was so friendly and knowledgeable. It was the best and most relaxing day of our trip to Italy. By the time he dropped us off in Siena, we felt like we had made a new friend! I highly recommend Fabio. A perfect day trip

Nancy🇺🇸 United States

29 July 2019

We had a great time traveling to Siena with Fabio! Before the trip, I told him what our group of 8 was interested in seeing and doing. He made suggestions and the day turned out wonderfully! He shared his knowledge about the country, the cities and the culture with us and his driving was impeccable! We had time to explore Siena on our own and then we had lunch/wine tasting at a wonderful, small vineyard and farm. I would definitely book a tour with Fabio again!Wonderful guide!

Andrea🇺🇸 United States

2 July 2019

Our family of five (including 20, 19 & 18) had a wonderful day with Fabio. He is so knowledgeable about the area around Florence. We went to Siena and then had a wonderful lunch and wine tasting at a small vineyard. The private tour was just what we wanted; get out of the crowds and enjoy getting to know someone who grew up in this area. Ciao Fabio, until next time! AMAZING GUIDE

Anne🇦🇺 Australia

20 June 2019

Fantastic day in Tuscan countryside with Fabio. We appreciated his knowledge and stories. Fabio shared his Tuscany with us. Thank you Fabio!A day trip back in time in Siena with a local

Dev🇮🇳 India

9 May 2019

We had a great Siena tour with Fabio. Lovely conversation, lovely car, lovely person. Very very knowledgeable and friendly. Knows a lots about World economics, history, culture and Siena. We had a great day with Fabio. Thanks Fabio. We will meet again soonThank you Fabio

Shanelle

8 May 2019

We had a great experience with Fabio. Fabio gave us great insights into the culture, lifestyle, economy, history of Italy. The Siena tour with him was truly fabulous. Fabio is a great conversationalist and his car was comfortable and super clean. Great for family trips and recommended for all.A day trip back in time in Siena with a local

Jean

21 October 2018

I would highly recommend Fabio. He was very flexible throughout our day, made terrific suggestions for places we would never have noticed without him and had a great sense of humor. All in all, he made our outing very special. Thank you Fabio!A Wonderful Day!

Terry

20 October 2018

We were a group of 8 and upon meeting Fabio he was a hit from the start! Such a nice, caring individual who shared his expertise. Would definitely give him an A+. Excellent Tour Guide

Melinda🇺🇸 United States

14 October 2018

We had an awesome day with Fabio. We had planned for a day trip to Siena. Fabio reached out to us prior to the trip to get a sense of what we wanted to do. He suggested stopping at a winery on the way, but we had just toured 3 wineries two days before. We told him maybe a quick stop in San Gimignano on our way to Siena, but we ended up deciding to just keep it simple with seeing only Siena. He picked us up on time, and once we were on our way, knowing we wanted to see a medieval town, he made an alternate suggestion, more on the way to Siena, with less crowds. It was FANTASTIC! He took us to a delicious pastry shop, and took us for a walking tour around this little town. Then we were off to Siena. He told us all about the Palio (horse race) that usually takes place twice a year but this year the mayor declared it a special year, and they were preparing for a 3rd Palio that is taking place towards the end of October. We visited Siena for awhile and then it was time to grab some lunch. Fabio took us to a friend of a friends popular restaurant and suggested some authentic Tuscan dishes for us all to share. The lunch was fabulous! We had a GREAT time with Fabio and truly enjoyed our day with him. My husband and I have been on a lot of tours, and Fabio has been one of the best we’ve experienced. He truly made an effort to tailor our day to the things we wanted to see, and for our group of 8 - we were not disappointed! Thank you Fabio!!!Fabulous time with Fabio!!!!

Duane 🇺🇸 United States

13 October 2018

Fabio was a fabulous host! He suggested a trip that was awesome and we had a fabulous time seeing Siena. He then suggested an awesome restaurant. All in all we had an awesome day with Fabio! He was fabulous! We would highly recommend him! Day trip back in time

Gus🇺🇸 United States

1 September 2018

Fabio was extremely knowledgeable, personable, and tailored the tour well for our family with young children. His recommendations exceeded our expectations, and he anticipated what we were hoping to experience better than we could ourselves. I would highly recommend him to anyone travelling in the area.A Day Trip Back in Time in Siena with a Local

Gitsel🇺🇸 United States

2 August 2018

Quisiéramos aprovechar para darte las gracias, el tour fue estupendo, la pasamos súper bien y hablamos en English, español y nos enseñantes italiano . El lugar es bellísimo y más aún toda la historia que lo envuelve. Excelente guía. Nos veremos en otra oportunidadA Day Trip Back in Time in Siena with a Local

jeannot

8 June 2018

Really enjoyed our time. Very informative. Learned a lot about the area (Siena and Firenze). Also added wine tasting and tour last minute which was excellent.A Day Trip Back in Time in Siena with a Local

Jeannot

8 May 2018

Fabio did a wonderful job showing us Siena. Very knowledgeable about the history and customs. He was open to what we wanted out of our day and arranged a winery tour and tasting very last minute which was excellent. As an added bonus we were picked up where we were staying so didn't have to try and find him at another location. Thank you for a wonderful day. Exceeded expectations

Janet🇺🇸 United States

7 February 2025

My husband and had a great day going to San Gimignano with Fabio. From pick up at our hotel in Florence to drop off, everything was wonderful. If you want to take a private day trip to this beautiful hilltop town known for its towers, don’t hesitate to use WithLocals and book with Fabio. He is knowledgeable, enjoyable to be with and kind enough to speak to me in Italian so I could practice mine! Una Splendida Giornata!

Sonal

19 November 2024

Fabio was outstanding in his knowledge and experience. He was very kind, courteous and accommodating and showed us around very well. Will recommend him and his extremely comfortable car to every one wanting to travel in Tuscany. Thank you Fantastic Fabio

Terri

29 October 2024

Fabio was an amazing tour guide picking us up in a clean and well maintained van and easily conversing with us like we were his friends. He spoke excellent English and understood all of our questions. He brought us to San Gimignano a charming medieval town on a hill top , completely walled in with churches, towers, and small shops. It was so beautiful even in the misty rain. He told us stories about the families' lifestyles from yesteryear all the way to the current status of its small bustling town with current wifi, technology , and amenities. We continued on to a small wine tour / tasting at I Balzini (as seen on the show The Succession ). We so enjoyed our time there learning, eating, drinking and conversing with our old friends and our new friend Fabio! Fabio was an amazing tour guide and I would highly recommend him. He was super easy to talk to, was knowledgeable, and made you feel very comfortable. Fabulous Tuscany with Fabio

Laurie🇺🇸 United States

26 October 2024

Fabio was a great guide and he personalized our tour beautifully. Would absolutely tour with him again! Wonderful Tour!

Jesse🇺🇸 United States

25 October 2024

Thank you Fabio for the fantastic day in Tuscany! You were very prompt in your communication leading up to the tour, had a nice, new and spotless van and were 100% professional. Your energy and knowledge made it easy to stay engaged. Thank you again and many recommendations to our friends and family in the future. Fantastic day!

Melanie🇺🇸 United States

14 October 2024

Fabio was fantastic! He was so knowledgeable and friendly, and everyone had an amazing time exploring Certaldo and a local winery. It was unforgettable, and we can’t wait to come back and see Fabio again! Highly recommend!!

Beth🇺🇸 United States

8 October 2024

Four of us had a charming day with Fabio. We enjoyed his historical knowledge of Italy as well as his wit. San Gimignano was beautiful but the highlight of the day was our lunch. We toured a small family winery and experienced an intimate food and wine pairing, lovely! Highly recommended Fabulous with Fabio

Sarah🇮🇲 Isle of Man

20 July 2024

What an amazing day and what a wonderful guide. Fabio collected us from our hotel in Florence and whisked us towards first Siena and then Sam Gimignano - all the while giving us the historical context of both places in a fun and informative way. He brought the Palio to life for our group (of 8 with ages ranging from 11 to 60) with funny anecdotes about inter district rivalries! In between the 2 sites visited we stopped for a delicious lunch and wine tasting which was a real highlight and we left having exchanged numbers with our hosts and laden with fabulous wines to take on to our next Villa! We all thought Fabio was an excellent and thoroughly knowledgeable guide and would recommend the experience highly to everyone. Ciao Fabio - grazie mille 🙏A fabulous day exploring Tuscan jewels

john🇺🇸 United States

18 April 2024

We had a great day with Fabio! He was full of information about the area and the history. Very friendly and accommodating. He exceeded our expectations. Day trip with Fabio

John🇺🇸 United States

27 March 2024

We spent a rainy day touring Siena, San Gimignano and a local winery with Fabio. Despite the rain, it was a lovely experience and I can’t imagine a better guide than Fabio. Would highly recommend to anyone!Fabio is amazing!

stephanie

11 November 2023

Fabio was easy to communicate with ahead of tour and customized for our needs. Knowledgeable, flexible with changes and made a special day for us in Tuscany including a stop at winery for tasting and lunch. Taught us all about wine region and provided much historical reference. Would book with him in our future Italian adventures and recommend to friends who visit Tuscany region. Amazing day in Tuscan town

Joan🇺🇸 United States

6 October 2023

We had a lovely day with Fabio. He is very well versed in history, past and present, so we had some interesting conversations. And a nice person to boot! We spent an unaccompanied hour or so wandering through San Gimignano and then he took us to a wonderful winery for lunch (extra cost that was worth every penny!). Diana, the owner of the vineyard, told us about the wines in between courses of fresh, delicious food. It was as close to a perfect day as you could ask for. Fabio was fabulous!

Tom🇨🇦 Canada

6 September 2023

Fabio gave us a great tour of San Gimignano. His knowledge of the history of the area was top notch and took the time to walk us through part of San Gimignano and explain all kinds of events, art and culture. On the way back to Florence he stopped at the most amazing restaurant for lunch too!! Loved that place!!Amazing personalized tour of San Gimignano

Elena🇺🇸 United States

30 June 2023

Fabio was a terrific guide who generously shared the intimate details of the local cultures of Florence, Pisa, and Lucca. He did an amazing job at making us feel like family more than tourists which really helped us sink into the movements of Italy and sparked a love and respect for this wonderful country. He also spoke great English which was necessary for our wonderful experience. Amazing and knowledgeable tour guide

Michael🇺🇸 United States

30 May 2023

Fabio is fabulous. His knowledge of all things Florentine and Tuscan is surpassed only by his enthusiasm for his home region. His excellent English skills were developed by living and traveling abroad, giving him a perspective that many other guides lack. He can converse on a very high level about virtually anything. His advanced education and intellect meld this background together to tailor a super personalized experience for his guests. It is evident that Fabio truly cares about his clients having a good experience. My wife, 3 adult children and I all had an amazing experience visiting San Gimignano and a small organic winery. Diana and her small staff provided a tour of their operations and vineyard and prepared a delicious Tuscan lunch paired with a wine tasting of their small production wines. The genuine warmth and hospitality shown to us was embracing - we didn't want to leave. We've seen a lot of great historical and renowned sites on this Italian vacation, but this day will forever be remembered by each of us as the very best day. Grazie, Fabio!Perfect Day

Vicente🇲🇽 Mexico

15 January 2023

He picked us up una very comfortable van, he shared all his history knowledge with us since the first minute, as well as his love for his land. He is very kind and has a great conversation. He took us to a great winery where we enjoyed wine tasting and had a tour of the cellars. I will definitively hire his services again the next time I come to Tuscany.Kind, knowldegable, the best!

Lynda🇺🇸 United States

1 January 2023

Our day in the Tuscan countryside with Fabio was one of the highlights of our Italy trip, it was amazing! Fabio is so knowledgable and a pleasure to spend the day with, he took us to the most incredible winery where we had a private tour and lunch, as well as San Gimignano. At first we weren't sure we wanted to spend a whole day outside of Florence but it was so worth it. I would recommend this to everyone, don't miss it!Don't miss this!

Hilary🇺🇸 United States

13 November 2022

We spent a wonderful day in San Gimignano and Certaldo with Fabio. He was knowledgeable and interesting. He had a large, clean van and drove well and was punctual. He has a vast knowledge of Italian and European history. He chose a wonderful restaurant with a view for us to celebrate our 39th wedding anniversary. We highly recommend Fabio!A Day in San Gimignano

Bill🇺🇸 United States

16 October 2022

I am a travel agent who booked for four women. They were in Italy for two weeks and called it the highlight of their visit. They could not have more to say about Fabio's excellent care, service and knowledge.Fabio simply the best.

Teresa🇺🇸 United States

13 October 2022

Fabio took us from Florence to San Gimignano, Fattoria Di Montemorli and his hometown of Certaldo. He is lovely and interesting. We enjoyed a beautiful day and learned about the areas. I would highly recommend joining Fabio when you visit!Wonderful day with Fabio!

John🇺🇸 United States

23 September 2022

Fabio gave us a great, memorable ay in Tuscany. He was punctual, very engaging and knew everything about Italian history, culture, wine and current events. Our trip to San Gimignano and his hometown, Certaldo, was perfect. 5 star experience!Great day in Tuscany!

Heather🇺🇸 United States

17 August 2022

Our group of 7 (4 adults and 3 kids) spent a lovely day with Fabio as he took us through Tuscany with a stop at San Gimignano and another stop at his friends winery/organic farm. It was a treat to get outside of Florence and experience a different pace and perspective. Every recommendation that Fabio made was perfect. He also did a great job of explaining the scenery as he drove and constantly tied facts and stories back to the history of Florence, Tuscany and Italy. Both kids and adults agreed, Fabio led one of our most special experiences from our 12 day Italy trip!Unique Tuscan Experience

Kelly🇺🇸 United States

14 July 2022

Our party of four had the opportunity to join Fabio on the Scenic Private Day Trip to San Gimignano. It was a wonderful day start to finish. Fabio picked us up at our Airbnb on time and off we went. As we were traveling he pointed out sights to us and gave us background information about the families who owned the vineyards and the cemetery for the American WW2 soldiers. We stopped to take some amazing pictures of the beautiful landscape before we arrived at Gimignano. Upon arrival at Gimignano we were given time to go exploring and shopping in town. After all of our shopping, Fabio took us to a wonderful winery Fattoria Di Montemorli. We had a wonderful tour and lunch was amazing. Great conversations and great wine! Thank you for a wonderful day. Fabulous Trip

David🇺🇸 United States

25 June 2022

Everything was perfect within our experience with Fabio. Great communication and easy to book the trip. I've never used the app before and didn't know what to expect, but everything was stop notch! Even though I communicated and set up a certain schedule with Fabio via messages exchanged through the app, I switched it up and made different plans and Fabio was easy to adapt to the new plans and make it a very enjoyable experience! He is very professional, but relaxed and laid back. Transportation was a new travel van that accommodated all of us comfortably. Last minute on the way back to our drop off point I realized I needed cash and Fabio located a post office in a nearby town and drove out of his way to make it easy on me. Everything about the trip was wonderful, the local winery tour - lunch was amazing and the wines were so good we bought cases of them and olive oil that they shipped back to the Staes for us, and the the visit to a local medieval village of Certaldo was exactly what we asked for and is what Fabio created for us. Thanks Fabio and we hope our travels cross your path again one day!Awesome Experience!

Liliya🇺🇸 United States

23 June 2022

We booked half day private tour with Fabio and it was the most wonderful experience we could wish for. He picked us up from our hotel on time and brought us back. I asked for a wine tasting a day before our trip and Fabio went above and beyond to book us a wine tasting with food pairing. It was a busy time so it was harder to book wine tasting last minute but Fabio found a place for us. After wine tasting we drove around Tuscany and visited Certaldo, a beautiful town with rich history. Fabio was very knowledgeable and gave us a lot of interesting information. He was pleasant, had nice, clean, air conditioned van, very accommodating to our needs, safe driver and just a great person to be around. We loved our trip with Fabio and highly recommend his services.Amazing time in Tuscany!

Ann Marie🇺🇸 United States

2 April 2022

Fabio provided one of the best days of our vacation. We traveled with our children (early 20s and late teens) and we all agreed he was our favorite guide of the trip. He is knowledgeable, gracious and attentive. He picked us up and dropped us off at our hotel. He is a very safe driver. He had perfect stops along the way for beautiful pictures. We enjoyed his company and wished we would have scheduled more experiences with him.Terrific experience! Fabio is excellent!

wendy🇺🇸 United States

29 March 2022

We had a day trip to San Gimignano with Fabio and it was perfect! Fabio met us at our apartment in Florence and drove us through Tuscany, sharing stories about the region, the life in Tuscany and his love for the area. We stopped along the way and we're able to explore a bit. Once in San Gimignano we wandered the city, ate gelato, and took in the history. Fabio gave us a history of the towers, adding great tidbits of history we did not know. Next we went on to a lovely, family owned vineyard and had an outstanding lunch and wine tasting. Overall is was a perfect day. Fabio is so knowledgeable, a great story-teller and quite witty! Truly an amazing guide and amazing day.Perfect!

Unknown

18 October 2021

Fabio was very informative and helpful. we enjoyed our 2 days of touring very much.Very Fun