When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and wander the storybook streets of the UNESCO-listed village San Gimignano. Group size is limited to 14 for a more personalized experience.

Full-day tour to the picturesque Tuscan countryside from Florence
Enjoy a sumptuous Tuscan lunch paired with Chianti wine
See why the hilltop village of San Gimignano earned UNESCO World Heritage status
Small-group tour limited to 14 people or fewer

What's Included

Expert English-speaking guide
Designated professional driver
Air-conditioned transport
Expertly guided walking tour of Siena
Expertly guided walking tour of San Gimignano
Gourmet lunch and wine tasting in Chianti

Gratuities
Hotel Pick-Up/Drop-Off

Meeting and Pickup

Meeting point

Piazza della Repubblica, 50123 Firenze FI, Italy
We meet by the Carousel in Piazza della Repubblica. Piazza della Repubblica is one of the main squares in the historical centre of Florence. In the middle of the square you will see a Carousel. We meet just by the Carousel, next to the ticket booth. Your guide will be holding a Walks sign.

Start time

08:30 AM

End point

This activity ends back at the meeting point.

What To Expect

Tuscany

1 hour 30 minutes • Admission Ticket Free

Siena

1 hour 30 minutes • Admission Ticket Free

Duomo di Siena

15 minutes • Admission Ticket Not Included

Piazza del Campo

15 minutes • Admission Ticket Free

Tuscany

3 hours • Admission Ticket Free

San Gimignano

1 hour 30 minutes • Admission Ticket Free

Piazza della Repubblica

1 hour • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
We are unable to accommodate guests with mobility limitations, wheelchairs, or strollers on this tour.
Not wheelchair accessible
In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8.
Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch.
If you are traveling with a small child, please contact us. We need to confirm space on the vehicle for them.

Near public transportation
Infant seats available
Most travelers can participate
Walks complies with all local government regulations. You may need to wear a mask or provide proof of vaccination to enter certain venues. Please refer to Italy government guidelines for the most up to date information.
This tour/activity will have a maximum of 14 travelers

Cancellation Policy

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

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.

Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.

Traveler Photos

Featured review

Shelly_A

A marvelous trip with excellent guide. Frederica was friendly, informative and a wonderful guide for our day together. The van was comfortable and the driver efficient. It was great di start at piazza Michelangelo for the view on our way out of town. Siena is beautiful and getting tickets for the Duomo is truly a must! Lunch was magnificent with the delicious regional wines to match the courses. Sam Gimingnano has lovely shops with great views of the countryside. I highly recommend this tour.

Reviews

4.5

179 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews

Reviews by Viator travelers.

We perform checks on reviews

Showing 1-10 of 179 reviews

Too many people on tour, 14, with only one guide. She rode in same van all day. We were in the other van with 8 people.

Ciro_M, Apr 2024

Lunch at winery was great but our guide kept talking and didn’t allow the wine expert to talk. Food and wine was very good. 14 people is too much for one guide. Very little free time in Siena and Gimignano.

Hidden gem

Kathryn_A, Apr 2024

Sandra (guide) and Francesco (driver) were wonderful. They both were very knowledgeable about Florence, Siena and San Gimignano including quaint cultural influences. Both answered all of our questions we had and made it a fun day. Sandra was very aware of the right pace to set in the hilly towns and gave the right level of information of what we were seeing. The wine tasting and lunch were very good and a hidden gem. Highly recommend this to give you an overview of the area.

Response from Host, Apr 2024

Dear Kathryn, Thank you for sharing your experience with us! It's fantastic to hear that Sandra and Francesco provided you with such an enjoyable and informative tour of Florence, Siena, and San Gimignano. Their knowledge and attention to detail seem to have made your day memorable and fun. Exploring the hilly towns can indeed be quite an adventure, and it's great to hear that Sandra struck the right balance between pace and information. We're delighted that you enjoyed the wine tasting and lunch, and we appreciate your recommendation. If you ever want to explore more hidden gems or delve deeper into the culture of other areas, we'd love to have you join us again for another unforgettable tour. Best regards, Oleksandra Walks & Devour Team

Highlights!

Susan_S, Apr 2024

It was a great day all around! Easy travel, knowledgeable guide, delicious wine lunch and time to enjoy the sights!

Response from Host, Apr 2024

Dear Susana, Thank you for sharing your positive experience with us! We're thrilled to hear that you had a great day exploring with us. It sounds like everything from the travel arrangements to the wine lunch and sightseeing went smoothly and exceeded your expectations. Our guides strive to provide insightful and enjoyable experiences, and we're glad to hear that yours did just that. If you ever want to embark on another adventure or explore new destinations, we'd love to have you join us again! Best regards, Oleksandra Walks & Devour Team

Not to be missed

Kristi_F, Apr 2024

The guide, the towns, and the trip overall was amazing. The highlight for everyone was the lunch and win tasting at the vineyard. Even those who weren’t super into wine said that was a highlight. Beautiful and a great selection of wines for every palate. I highly recommend this tour. Of the many tours we took, this one is at the top.

Response from Host, Apr 2024

Dear Kristi, Thank you for your enthusiastic feedback! It's fantastic to hear that you enjoyed your experience with us, particularly the lunch and wine tasting at the vineyard. We strive to provide memorable experiences that cater to everyone's interests, and we're thrilled to hear that even those who weren't initially keen on wine found it to be a highlight. Your recommendation means a lot to us, and we're delighted to know that this tour stands out as one of your top experiences. If you ever find yourself in need of more memorable tours in the future, we'd love to welcome you back! Best regards, Oleksandra Walks & Devour Team

A great day in the Tuscan countryside

Dan_B, Apr 2024

This was a truly wonderful experience, despite the rain in San Gimignano. Our guide, Antonio, and driver, Renaldo were great. Antonio was very well-informed of the region's history and he provided us with lots of good information. The lunch and wine tasting were perfect. We'd highly recommend this tour!

Response from Host, Apr 2024

Dear Dan, Thank you for your wonderful review! It's fantastic to hear that despite the rain, you had a truly wonderful experience on the tour! Antonio sounds like an excellent guide, knowledgeable about the region's history and passionate about sharing it with you. The lunch and wine tasting must have been a perfect way to unwind and enjoy the local flavors. Thank you for recommending the tour! If you ever find yourself exploring other regions or destinations, we'd love to have you join us again for another memorable experience. Best regards, Oleksandra Walks & Devour Team

Wonderful day trip in Tuscany

Timothy_K, Apr 2024

This was a very nice way to see Siena (highly recommended), a Tuscan medieval village frozen in time, and enjoy great food and wine in Chianti. Antonio our guide was very nice and informative and helped make the whole day a great experience with our new friends. This was one of our favorite experiences during our first trip to Italy.

Response from Host, Apr 2024

Dear Timothy, Thank you for sharing your experience with us! We're delighted to hear that you enjoyed your time exploring Siena and indulging in great food and wine in Chianti. Antonio sounds like an excellent guide, and we're glad he helped make your day memorable. It's fantastic to know that this experience was one of your favorites during your first trip to Italy. Siena truly is a gem, and we're thrilled that we could contribute to your memorable experience. If you ever plan to visit Italy again or explore other destinations, we'd love to have you join us for more unforgettable experiences. Best regards, Oleksandra Walks & Devour Team

Great guide and outstanding lunch

Donald_K, Mar 2024

Patrizia was a wonderful guide and shared so much information about Siena and San Gimignano. The drive Fabio was also outstanding. Learned a lot about the region and its history. This also included lunch at a winery. I’ve done tours like this before where lunch is included and generally unmemorable. This lunch was quite good and possibly the best meal I’ve had in Italy so far. Worth every penny.

Response from Host, Apr 2024

Dear Donald, Thank you for your glowing review! We're delighted to hear that you had a wonderful experience with Patrizia and Fabio, learning so much about Siena, San Gimignano, and the region's history. It's fantastic to know that the lunch at the winery surpassed your expectations and was possibly the best meal you've had in Italy so far. We're thrilled that you found the tour worth every penny. We hope to have the pleasure of welcoming you back on another memorable tour soon! Best regards, Oleksandra Walks & Devour Team

Nice daily trip to two historic towns in Tuscany with excellent lunch at a winery in between

Turul_D, Dec 2023

On a cool yet crisp and sunny day, we met our tour guide Ismael and the drivers of two Mercedes vans waiting at the Piazza della Repubblica at 8:15 where we were kindly asked to remain outside until the others arrived. Since these smaller Mercedes vans are 3+3 seaters behind the driver, you may end up seating separately from your significant other if there happens to be 6 passengers in a van. At 8:30, the 10 people in the tour were dispatched to the two vans as 6+4 and we were on our way with our driver Stefano to our first stop at Piazzale Michelangelo to enjoy the panoramic view of Florence with the Arno river and take photos before we left for Siena. Since there was a single guide, Ismael needed to change his van at each stop. We arrived in Siena at about 9:50, an hour after leaving Florence, and started our tour of this beautiful town, eventually heading to Piazza del Campo, where they hold horse races twice a year on sand. Ismael was quite knowledgeable and filled us in with many interesting pieces of information as we continued our walk to the famous Siena cathedral. We parted there on the hilltop about an hour after our arrival in Siena to explore the town on our own until noon. We certainly recommend visiting the beautiful cathedral. Then we headed to Castellina in Chianti to arrive about half an hour later and have lunch while tasting five different kinds of wine. Our sommelier Francesca provided lots of information during our visit of about 15 minutes to their production facilities and cellars which lie at the heart of the Chianti Classico area after which we moved to the restaurant upstairs where there was a cozy fireplace burning. The excellent lunch which included Tuscan food ended with a special kind of dessert wine and cookies. It was about 14:15 when we left Poggio Amorelli and drove to San Gimignano, which is another lovely historic town again on a hilltop. We arrived there at about 15:00 and had a guided walk to the main square of this smaller town famous for its towers and parted at about 15:15 to explore on our own for about an hour. It was dark when we were back in Florence. In summary, this was a nice daily trip to two historic towns in Tuscany with excellent lunch at a winery in between while you enjoy the beautiful panaromic view of the surrounding Tuscan countryside along the way.

Response from Host, Jan 2024

Dear Turul_D, Thank you for sharing your detailed and delightful experience on our Tuscany tour. We're thrilled to hear that Ismael, Stefano, and Francesca contributed to making your day special. Your vivid description of the journey through Siena, Castellina in Chianti, and San Gimignano is appreciated. We're delighted to have been part of your exploration of Tuscany, and we look forward to welcoming you on more memorable adventures. Thank you for sharing your detailed and delightful experience on our Tuscany tour. We're thrilled to hear that Ismael, Stefano, and Francesca contributed to making your day special. Your vivid description of the journey through Siena, Castellina in Chianti, and San Gimignano is appreciated. We're delighted to have been part of your exploration of Tuscany, and we look forward to welcoming you on more memorable adventures. Best regards, Sasha

Perfecto!

jennifer_b, Nov 2023

This was a lovely day trip from Florence. One of the highlights for both of us! Great guide and driver so you didn’t have to worry about anything. Charming Tuscan countryside villages with rich history. Winery tasting and lunch was excellent. Chianti wine isn’t a wine I usually drink but liked trying it. I would definitely recommend this tour!

Response from Host, Apr 2024

Dear Jennifer, Thank you for sharing your experience with us! We're thrilled to hear that you had a lovely day trip from Florence and that it was one of the highlights for both of you. It's fantastic to know that you found our guide and driver great, providing a worry-free experience. Exploring the charming Tuscan countryside villages with rich history sounds delightful, and we're glad you enjoyed the winery tasting and lunch, finding it excellent. It's always wonderful to try something new, and we're glad you liked tasting Chianti wine, even if it's not usually your go-to. Your recommendation means a lot to us! If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Awesome incredible

Vic_F, Nov 2023

Everything. Visiting both cities and lunch at winery’learning the history of these cities and seeing them in person. Incredible

Response from Host, Apr 2024

Dear Vic, Thank you for sharing your experience with us! We're thrilled to hear that you enjoyed everything about your tour, from visiting both cities to lunch at the winery and learning the history of these incredible places firsthand. Exploring the cities and experiencing their history in person can truly be an incredible experience, and we're glad we could provide that for you. If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more unforgettable experiences! Warm regards, Oleksandra Walks & Devour Team

Tuscan countryside - Enjoyable and easy day trip!

Brian_B, Oct 2023

Very easy pick-up at the Piazza Republica. Lovely quick stop at the Piazalle Michelangelo for photos and history. Elena the tour guide is very friendly, outgoing and knowledgeable sharing her knowledge and personal insights. She is very welcomng and really helped to make sure that we were able to absorb details as we toured Siena and San Gimingano. We especially appreciated her story about the Palio and that she was able to obtain skip the line tickets for the Siena cathedral. It felt like she really wanted for everyone to get the most out of the visit. Highly recommend this tour.

Response from Host, Apr 2024

Dear Brian, Thank you for sharing your experience with us! We're delighted to hear that you had a wonderful time on the tour and that everything went smoothly from the easy pick-up at Piazza Republica to the lovely stop at Piazalle Michelangelo for photos and history. We're thrilled to hear your positive feedback about Elena, your tour guide. It's fantastic to know that she was friendly, outgoing, and knowledgeable, sharing her insights and ensuring that everyone could absorb the details as you toured Siena and San Gimignano. We're glad you appreciated her story about the Palio and that she was able to obtain skip-the-line tickets for Siena Cathedral, enhancing your experience. Your recommendation means a lot to us! If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Super fantastic!

Nena_H, Oct 2023

The lunch and wine tasting was fantastic! One of the best meals ever! Our tour guide was awesome! We enjoyed learning about Sienna and San Gimlango! Enjoyed the views, shopping and gelato!

Response from Host, Apr 2024

Dear Nena, Thank you for sharing your feedback with us! We're thrilled to hear that you had a fantastic experience with the lunch and wine tasting being a highlight of your tour. It's wonderful to know that you had one of the best meals ever and that you enjoyed every aspect of it. We're glad to hear that your tour guide was awesome and that you enjoyed learning about Siena and San Gimignano. Exploring the views, shopping, and indulging in gelato sounds like the perfect way to complement your tour experience. If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences! Warm regards, Oleksandra Walks & Devour Team

A Oerfect Day

BruceS_F, Oct 2023

Our lunch in Chianti was most memorable. Our host was friendly and informative. The food was SO fresh. Our guide and driver were both welcoming and helpful. Both Mid evil towns were fun to visit.

Response from Host, Apr 2024

Dear Bruce, Thank you for sharing your feedback with us! We're delighted to hear that your lunch in Chianti was a memorable highlight of your tour. It's wonderful to know that your host was friendly and informative, creating a welcoming atmosphere for you to enjoy the delicious, fresh food. We're glad to hear that both your guide and driver were welcoming and helpful throughout the tour, ensuring you had a seamless and enjoyable experience. Exploring the medieval towns must have been a fantastic experience, offering glimpses into history and charm. If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more unforgettable experiences! Warm regards, Oleksandra Walks & Devour Team

A delightful sightseeing and gastronomic experience!

Anthony_V, Oct 2023

This too is a great way to combine panoramic views of Florence with insightful and interesting guided tours of Siena and San Gimignano together with an excellent lunch of traditional Italian food and a variety of wines. Our guide, Anika, was terrific.

Response from Host, Apr 2024

Hi there! Thank you for your feedback! We're thrilled to hear that you enjoyed the panoramic views of Florence along with the guided tours of Siena and San Gimignano, as well as the excellent lunch and wine tasting experience. It's wonderful to know that Anika, your guide, made the experience even more enjoyable with her insightful and interesting commentary. We'll be sure to pass along your kind words to her! If you ever find yourself back in Italy or exploring other destinations, we'd love to welcome you back for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Dream come true

Deirdre_F, Oct 2023

Seeing sienna and the wine tasting with lunch was wonderful! The tour guide was very informative and enthusiastic and fun!

Response from Host, Apr 2024

Hello! We're delighted to hear that you had a wonderful time visiting Siena and enjoying the wine tasting with lunch! It's fantastic that you found the tour guide to be informative, enthusiastic, and fun – that's exactly the experience we aim to provide. If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences! Warm regards, Oleksandra Walks & Devour Team

Great Day Out

Barry_M, Oct 2023

It was a relief to escape some of the crowds in Florence, and to head out into Tuscany on this excellent trip. About 12 of us in all, loaded into two separate vans. Knowledgeable guide showed us the main sights of Siena first, followed by some free time - and then on to the Chianti vineyard for a quick tour followed by an excellent lunch with wine tastings for each course. The afternoon saw us travel on to the amazing San Gemignano, with plenty of time to wander round the town and take in the atmosphere. Good value overall, and recommended.

Response from Host, Apr 2024

Dear Barry, Thank you for sharing your experience with us! We're thrilled to hear that you enjoyed your escape from the crowds of Florence and ventured into the beautiful Tuscan countryside on our trip. It's fantastic to know that you found the knowledgeable guide to be informative as they showed you the main sights of Siena. The free time allowed for exploration and relaxation, setting the perfect pace for the day. The visit to the Chianti vineyard sounds delightful, with a quick tour and an excellent lunch accompanied by wine tastings for each course. Exploring San Gimignano must have been a highlight, and we're glad you had plenty of time to wander around and soak in the atmosphere of this amazing town. Thank you for recommending our tour! If you ever find yourself back in Tuscany or exploring other destinations, we'd love to welcome you back for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Wonderful all day tour with wine, food, sites and experiences you won't forget!

JetJouett_W, Sep 2023

Wonderful small group tour with a fantastic guide. We visited a family owned winery and hotel in Chianti, a tour of the the winery and a wine pairing lunch with fantistic food and fun! Siena is a little commercialized since I was there before and a lot of people! San Gigninamo is my favorite medieval town and alway fantistic views from on top the the city! I would recommend this tour and I have gone on it twice in 20 years, always great!

Response from Host, Apr 2024

Hi there! Thank you for sharing your experience with us! We're delighted to hear that you enjoyed your small group tour with us, especially with such a fantastic guide leading the way. Exploring the family-owned winery and hotel in Chianti sounds like a delightful experience, especially with the tour of the winery and the wine pairing lunch featuring fantastic food and plenty of fun! While Siena may have been a bit crowded, it's great to hear that you still enjoyed the visit. And we're thrilled that San Gimignano remains your favorite medieval town, offering fantastic views from atop the city. Thank you for recommending our tour, and we're honored that you've chosen to join us twice over the past 20 years. We look forward to welcoming you back for more unforgettable experiences in the future! Warm regards, Oleksandra Walks & Devour Team

Wonderful day in Tuscany

James_D, Sep 2023

Our guides, Mateo and Sara, were excellent; warm, friendly, and very knowledgeable. It was a very fun,, adventurous day❣️

Response from Host, Apr 2024

Dear James, Thank you for sharing your experience with us! We're thrilled to hear that you had an excellent day with our guides, Mateo and Sara. It's wonderful to know that they provided a warm, friendly atmosphere and shared their extensive knowledge with you throughout the tour. We're delighted that you found the day to be both fun and adventurous – that's exactly the experience we aim to provide for our guests! If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Must do day trip to Tuscany

Stephanie_M, Sep 2023

Great guide and really liked the small group and use of minivans to travel. Good balance of tour time and free time. Great variety of activities in itinerary.

Response from Host, Apr 2024

Hi there! Thank you for your feedback! We're thrilled to hear that you enjoyed your experience with us and that you found our guide to be great. It's fantastic that you appreciated the small group size and the use of minivans for travel, as well as the balance between guided tour time and free time for exploration. We're delighted that you found the itinerary to offer a great variety of activities – that's exactly what we aim to provide for our guests! If you ever find yourself back in the area or exploring other destinations, we'd love to have you join us again for more memorable experiences. Warm regards, Oleksandra Walks & Devour Team

Undoubteduly a well organized day of discovering the Tuscan countryside adjacent to Florence.

Theresa_B, Sep 2023

The wine tasting/homemade lunch at a small Chianti vineyard was lovely . . . and I ended up with lots of wine being sent home! All of the guides/drivers/proprietors were lovely and passionate about the culture and beauty of Tuscany.

Response from Host, Apr 2024

Dear Theresa, Thank you for sharing your experience with us! We're thrilled to hear that you enjoyed the wine tasting and homemade lunch at the small Chianti vineyard – it sounds like a delightful experience, especially with lots of wine to enjoy at home! It's wonderful to know that all of our guides, drivers, and proprietors were lovely and passionate about sharing the culture and beauty of Tuscany with you. Creating memorable and immersive experiences for our guests is always our top priority! If you ever find yourself back in Tuscany or exploring other destinations, we'd love to have you join us again for more unforgettable experiences. Warm regards, Oleksandra Walks & Devour Team

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