Siena and San Gimignano from Rome: Wine Tasting Tour in Tuscany
Recommended by 94% of travelers
Badge of Excellence
Rome, Italy
- 10 hours (approx.)
- Pickup offered
- Group discounts
- Mobile ticket
- Offered in: English
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Overview
If you’re short on time but want to make the most of your visit to Italy, experience the famous Tuscan countryside with this full-day tour from Rome. Travel by air-conditioned minivan to a landscape of rolling hills, olive groves and vineyards, stopping to stroll through the UNESCO-listed hilltop village of San Gimignano. Visit a winery in the famed Chianti region for a tour and tasting with appetizers, and explore the well-preserved medieval city of Siena.
- Enjoy a day away from the hustle and bustle of the city
- Upgrade your day by choosing for the private tour option
- Explore the local streets on a walking tour of the city
- Hassle-free round-trip transport from Rome makes things a breeze
Why Travelers Choose This Tour
As well as Siena and San Gimignano, this tour includes 10 wines and a local lunch at a 13th-generation winery.
What's Included
- Free transfer offered by Welcome Italy in air conditioning Minivan
- Free Pick-up and drop-off to the Hotels, Appartments, Bed&Breakfast
- 2 hours visit of Siena with your tour leader
- Visit of San Gimignano, the city of 100 towers
- Tasting of wines and local products in a famous cellar
- Tour guides during the whole trip
- Experience a Semi-Private Tour
- Siena Cathedral entrance tickets
- Tips
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
- Free Pick-up and drop-off to the Hotels, Appartments, Bed&breakfast, accomodations in the city center - The address must to be provided on the reservation. - Please contact customer services one day before the tour to confirm the pickup time. - Please wait in the hotel lobby or outside your accommodation 15 minutes before your scheduled pickup time
Start time.7:00 am
Itinerary
1
Basilica Cateriniana Di S. Domenico
20 minutes • Admission Ticket Free
2
Duomo di Siena
20 minutes • Admission Ticket Not Included
3
Centro Storico di Siena - World Heritage Site
1 hour • Admission Ticket Free
4
Historic Centre of San Gimignano
45 minutes • Admission Ticket Free
5
Tenuta Torciano
2 hours • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Stroller accessible
- Infants must sit on laps
- Infant seats available
- Most travelers can participate
- Provide the Correct address of your accommodation , hotel, B&B
- Pickup service only in the city center inside the Aurelian Walls
- Provide the correct phone number with international country code
- check that you provide all the details to the agency
- Without this information we can not guarantee the correct service
- Free transfer offered by Welcome Italy in air conditioning Minivan
- Emergency number also operational via whatsapp
- One day before call to confirm the pickup
- This tour/activity will have a maximum of 48 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.8
based on 136 reviews
Review summary
Last 12 months
22 reviews
Select a theme to learn more
Travelers consistently praise the tour guides for their deep knowledge, engaging storytelling, and friendly demeanor, which enrich the historical and cultural experience. Drivers are noted for their professionalism, skillful navigation, and safety focus, contributing to a positive and comfortable journey. Overall, the combination of knowledgeable guides and attentive drivers creates an enjoyable and well-rounded tour experience.
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Excellent Tour. Our guide and driver were sisters and they were very professional and fun to be with for the entire trip. Highly Recommend them and the trip.
Response from Host, Oct 2026
Thank you for your kind review! We’re delighted that your guide and driver made the trip both professional and fun the sister duo will be so pleased to hear your feedback! Thank you for recommending them and the tour. We hope to welcome you back soon!
This tour is one of our favorites. Monica was extremely knowledgeable and thoughtful throughout the tour. She made all the difference for us to enjoy an unforgettable experience. Our tour driver, Adam, was an excellent driver. It was very relaxing knowing we were in good hands throughout our travels. We highly recommend this tour!
Response from Host, Jul 2026
Thank you so much for your wonderful review. We’re delighted to hear that this tour became one of your favorites and that Monica made such a meaningful difference with her knowledge, thoughtfulness, and attention throughout the day. Adam will also be very happy to know that his professional driving helped you feel relaxed and comfortable during the journey. It means a lot to us to know that the experience was so memorable for you. Thank you sincerely for your recommendation and for choosing our tour. We hope to welcome you back to Tuscany for another unforgettable day.
We were picked up and dropped off at our hotel. The driver and tour guide were friendly and professional. Our guide, Monica, was very knowledgeable and she answered all of our questions. The trip was scenic and whenever we came across a landmark (that was on our way to a destination), Monica took the time to tell us all about it. We made a stop when we left and we came back (for bathroom and snacks), which we needed and appreciated. At our two stops prior to the winery, we were able to walk around on our own, which allowed us to shop. The winery was soooo much fun! It is beautiful. We tasted about 9 wines and we ate delicious food. The staff was super friendly.
We have done the San Gimignano and Siena tour before but this time around, we saw different parts and heard new information. It was WONDERFUL! We would do it again and again and we will recommend this tour to our families and friends.
Response from Host, Jul 2026
Thank you so much for sharing such a detailed and thoughtful review. We’re delighted to hear that you enjoyed the entire experience, from the comfortable hotel pick-up and scenic journey to the time spent exploring Siena and San Gimignano at your own pace. Monica will be very happy to know that her knowledge, professionalism, and attention throughout the day made such a positive impression, and we’re equally pleased that your driver helped make the journey smooth and comfortable. It’s wonderful to hear that the winery was such a highlight, with its beautiful setting, delicious food, generous wine tasting, and welcoming staff. We especially appreciate hearing that, even though you had visited Siena and San Gimignano before, this tour still offered you new places to discover and new stories to enjoy. Thank you sincerely for your recommendation and for choosing to travel with us again. We would be truly happy to welcome you back for another memorable experience in Italy.
This day trip was excellent! Monica was a very informative, patient, and knowledgeable guide. Natalia was an awesome driver. We loved Siena! The town was beautiful. Be advised there were many steep hills that we struggled to walk up and down during the walking tour. San Gimignano was less impressive and still had steep hills to walk. Even with this, Monica helped us and was always willing to assist us on the walking tours. The final stop was the wine tasting. The food was delicious. Be advised, they are trying to sell their wine and the sommelier did a lot of talking to try and convince us.
Response from Host, Jul 2026
Thank you very much for sharing your experience with us. We’re delighted to hear that you enjoyed the day and especially appreciated Monica’s knowledge, patience, and care, as well as Natalia’s excellent driving. Siena and San Gimignano are both beautiful historic towns, although their medieval streets and steep hills can certainly make the walking portions more challenging, and we’re very pleased to know that Monica was always attentive and ready to assist you along the way. We’re also glad you enjoyed the food during the wine tasting. As the tasting takes place at a working winery, the sommelier also presents the estate’s wines and products, but of course there is never any obligation to purchase. Thank you again for your thoughtful feedback and for choosing to spend the day with us. We truly hope to welcome you again on another experience in Italy.
An absolute "must do", when visiting Italy. A great company, informative guide and safe trip. The best day tour we have ever done, and I just can't recommend them more in every respect. And such a lovely lunch and wine tasting experience.
Just a fantastic experience
Response from Host, Jun 2026
Thank you so much for your wonderful review. We are truly delighted to hear that you considered this one of the best day tours you have ever experienced. It is especially rewarding to know that you enjoyed the organization of the tour, the knowledge of your guide, the safe and comfortable journey, and the lunch and wine tasting experience. Your kind words and recommendation mean a great deal to our entire team. Thank you for choosing to travel with us, and we hope to welcome you back to Italy for another fantastic experience in the future
The Tuscan region is GORGEOUS! Our tour guide, Juliana was a wonderful guide who speaks great English! Our driver, Artur, also did a fantastic job of navigating the crazy traffic in Rome! I would highly recommend this tour!
Response from Host, May 2026
Thank you so much for your wonderful review! We’re thrilled to hear that you enjoyed the beauty of the Tuscan region it truly is one of the most breathtaking areas of Italy. Juliana will be very happy to know that her guidance and English-speaking skills helped make your experience even more enjoyable, and we’re also delighted that Artur’s professionalism and driving made you feel comfortable throughout the journey, especially in Rome’s busy traffic. Thank you again for your kind recommendation and for choosing our tour. We hope to welcome you back for another unforgettable experience in Italy soon!
Ease of use to see other parts Italy. Drivers professional safe. Tour guide very knowledgeable, friendly, helpful. Thank you
Response from Host, May 2026
Thank you so much for your kind words! We’re delighted to hear that you found it easy to explore different parts of Italy and that our drivers and tour guide met your expectations. Providing professional, safe service and knowledgeable, friendly assistance is exactly what we strive for, so it truly means a lot to know you had such a positive experience. Thank you again for choosing us we hope to welcome you back to Italy in the future!
Overall it was a great tour. The only concern was, Siena is a beautiful place and we did not get to see the whole place and explore on our own. We only were given 15 mins which was too short of a time. However, in the winery they gave us 4 hours to drink and offered to buy some wines. I wish we had more time in Siena instead rather than drinking. For the 4 hrs in the winery, we had wine tasting but not a tour of the vineyard which was quite odd as well.
Response from Host, Apr 2026
Thank you very much for your feedback we are pleased to hear that you overall enjoyed the tour and appreciated the experience we understand your comments regarding the time spent in Siena and at the winery and we truly value your perspective we would like to clarify that the itinerary is carefully designed to provide a balanced experience including both cultural visits and relaxation time at the winery which is one of the highlights of the tour and highly appreciated by many of our guests the duration of each stop is planned in advance to ensure the smooth running of the day and to respect all scheduled activities regarding the winery experience our partners are selected for their quality and professionalism and the tasting format may vary depending on the estate and their offerings however we always ensure a high standard of service we are proud of our team and partners who work with great dedication to deliver memorable experiences while we understand that preferences may differ we truly appreciate your feedback as it helps us continue to improve we hope to have the opportunity to welcome you again in the future
We spent one week in Rome and the surrounding area, and this was by far our favorite day. Joseph was our tour guide and Luigi our driver, they both were wonderful! Joseph was so much fun and provided great information. He set the tone for a wonderful day. After several hectic days in Rome, this was a nice reprieve. Slow-paced Sienna was such a nice change. The winery was beautiful and the staff there could not have been better. Highly, highly recommend!
Response from Host, Apr 2026
Thank you so much for your wonderful review we are truly delighted to hear that this was your favorite day during your time in Rome it is fantastic to know that Giuseppe and Luigi made such a positive impact and helped create a relaxed and enjoyable experience we are especially pleased that you appreciated the slower pace of Siena and the beauty of the winery your kind recommendation means a lot to us and we hope to welcome you again for another memorable experience
Overall the trip was worth it. Our drivers Arto and Antonio were very nice and Elizabeth our was knowledgeable of the history of both Siena and San Gimignano. The winery chosen was pretty and food was good.
Response from Host, Apr 2026
Thank you very much for your kind review we are delighted to hear that you found the trip worthwhile and that Artur Antonio and Elisabetta contributed to making your experience enjoyable it is wonderful to know that you appreciated the history shared during the visits as well as the winery and its food we truly appreciate your feedback and hope to welcome you again soon
We had a fantastic trip to Siena and San Gimignano, made truly memorable by our wonderful guide and driver.
Monika was incredibly informative, sharing rich historical context about both Siena and San Gimignano in a way that was engaging and easy to follow. Having lived in Siena herself, she brought an added layer of authenticity with local insights and personal perspectives that really enhanced the experience.
Our driver, Natalie, was equally impressive—professional, kind, and courteous throughout the journey. She ensured we were comfortable at all times, making the day feel smooth and relaxing.
A special highlight was our lunch and wine tasting at the winery, which was absolutely delightful. The lasagne, in particular, was the best we’ve had to date.
One note of feedback: one of our guests was not of legal drinking age, and it would be helpful if there were a different pricing option for guests who are unable to participate in the wine tasting portion of the experience.
Overall, it was a beautifully curated experience, and we’re grateful to Monika and Natalie for making it so enjoyable.
Response from Host, Apr 2026
Thank you so much for your wonderful and detailed review! We’re truly delighted to hear that your trip to Siena and San Gimignano was such a memorable experience. It’s fantastic to know that Monika’s knowledge and personal connection to Siena added depth and authenticity to the tour and made the history so engaging. We’re also very happy to hear that Natalie ensured a smooth comfortable and relaxing journey throughout the day. We’re especially pleased that you enjoyed the winery experience and that the lunch was such a highlight it’s always great to hear when it becomes a memorable part of the trip. Thank you as well for your helpful feedback regarding pricing for guests not participating in the wine tasting we truly appreciate this suggestion and will take it into consideration as we continue to improve our offerings. We’re very grateful for your kind words and hope to welcome you again soon for another beautifully curated experience!
Antoinette was our guide and Pietro was our driver. Antoinette was wonderful, warm and knowledgeable. It felt like ai was spending time with an old friend learning all about our surroundings.
Pietro was an excellent driver. He got us to all of our locations safely and comfortably.
I was ecstatic that it was just the four of us. It felt like a private tour which was exactly what I was hoping for!!
Response from Host, Apr 2026
Thank you so much for your wonderful review we are truly delighted to hear that Antoinetta made your experience so warm engaging and memorable and that Pietro ensured a safe and comfortable journey throughout it means a lot to know that the tour felt personal and special just as you had hoped we sincerely appreciate your kind words and hope to welcome you again for another great experience
Amazing tour.
Our guide, Stephano, was amazing, very knowledgeable and sweet. The wine testing was incredible.
Response from Host, Nov 2025
Thank you so much for your lovely review! We’re delighted to hear that you enjoyed the tour and the wine tasting experience. It’s wonderful to know that your guide helped make the day so special. We hope to see you again soon for another unforgettable experience with us!
This is a top notch experience, especially if you don’t have enough time to viisit Siena and Tuscany. Giuseppe and Luigi once again provided excellent service, very accommodating, flexible , with a personalized service! Wine tasting with lunch at San Gigmiano was the best ever! This is a must in Tuscany! Once again our tour guide and driver delivered the best service! Thank you Welcome Italy
Response from Host, Nov 2025
Thank you so much for your wonderful review! We’re thrilled to hear that you enjoyed your Siena and San Gimignano tour and that the wine tasting experience was unforgettable. It’s always a pleasure to know that Giuseppe and Luigi provided excellent, personalized service once again they truly love making every guest’s day special. We’re grateful for your kind words and hope to welcome you back soon for more memorable adventures with Welcome Italy!
This tour ended up being just me and my husband with our guide, Pino, and our driver, Artur. From the moment we left Rome for Siena, we were already joking around like we’d known them for years. Pino (also known as Giuseppe, Joseph, or Pepe—take your pick) was funny, entertaining, and ridiculously knowledgeable.
Siena is small but full of surprises. We learned so much about the life of St. Catherine of Siena without anything feeling too serious or museum-lecture heavy. Lunch at the winery was delicious and definitely catered to carnivores—but don’t worry, they’ll throw some vegetables at you too if that’s your thing.
San Gimignano is stunning, like a medieval fairytale village that somebody forgot to turn into a movie set. Amazing day, great company, and honestly, it felt more like a road trip with friends than a tour.
Response from Host, Nov 2025
Thank you so much for your amazing review! We are thrilled to hear that your tour of Siena and San Gimignano with Pino and Artur exceeded your expectations. It’s wonderful that from the very start, the day felt relaxed and fun, almost like traveling with old friends. Pino’s humor, knowledge, and engaging storytelling make history come alive without ever feeling heavy or formal, and we’re delighted that you appreciated learning about the life of St. Catherine of Siena in such a lively way.
We’re also glad that the winery lunch was enjoyable and suited your tastes it’s great that you could experience authentic Tuscan cuisine in a beautiful setting. And of course, San Gimignano’s fairytale charm is always a highlight, so it’s wonderful to know it left such an impression.
Your description of the day as a “road trip with friends” is exactly the experience we aim to create personalized, comfortable, and memorable. Thank you again for taking the time to share your feedback; it means so much to us and to our team. We would be thrilled to welcome you on another adventure in Italy anytime!
Tour manager Teresa & driver Roberto were fantastic! From the time they picked us up at our hotel to the time they dropped us back off, they took great care of us. Teresa was very knowledgeable, professional and courteous. She ensured our safety and that we were enjoying ourselves. The trip there & back was planned & coordinated to perfection! The wine was great & the food was delicious. Thank you Teresa for an amazing & awesome experience!
Response from Host, Oct 2025
Thank you so much for your wonderful feedback! We’re delighted to hear that Teresa and Roberto took such great care of you throughout the entire tour. It’s fantastic that Teresa’s knowledge, professionalism, and attentiveness made your experience both safe and enjoyable. We’re glad you enjoyed the wine, food, and seamless coordination of the trip. Thank you again for sharing your experience, and we hope to welcome you back for more amazing adventures soon!
We had a great time. My wife 😍 needed to walk slowly with a cane and she was not rushed or left behind like many other tours. Our guide kept everything at her pace. Great job!
Response from Host, Oct 2025
Thank you so much for sharing your experience! We’re delighted to hear that your wife felt comfortable and supported throughout the tour, and that our guide was attentive to her pace. Making sure every guest feels included and cared for is very important to us. We’re glad you both had a great time and hope to welcome you back for more wonderful experiences!
This experience was amazing! Can’t call it anything else.
Big shout out to Sam and Roberto our guide and driver who were excellent.
There are a lot of steep areas but Sam gave us plenty of time to do these. Take/ be prepared to buy a lot of water as we had a very hot and humid day but the towns were beautiful and so worth the drive and the walking.
Wine tasting was an excellent way to end the day.
Response from Host, Sep 2025
Thank you so much for your wonderful feedback! We’re thrilled to hear that your experience was truly amazing.
Sam and Roberto will be delighted to know they made such a positive impression. We’re glad Sam paced the day well and that you enjoyed the beautiful towns despite the challenging terrain and weather. Staying hydrated is definitely key on those hot days!
Ending with a wine tasting sounds like the perfect way to unwind, and we’re so happy it was a highlight for you.
We appreciate your kind words and hope to welcome you back for another memorable tour soon.
Beautiful drive to Tuscany. Walking through the towns was like walking through a history book. Finishing the day with a light lunch and a wine tasting was a perfect way to experience Tuscany. It was an easy drive from Rome. Sam and Jordan were awesome guides
Response from Host, Aug 2025
Thank you for your wonderful feedback!
We’re thrilled to hear that you enjoyed the beautiful drive through Tuscany and that exploring the charming towns felt like stepping back in time. It’s great to know that the light lunch and wine tasting were the perfect way to end your day.
Sam and Jordan will be delighted to hear your kind words they truly love sharing the beauty and history of Tuscany with our guests.
We appreciate your review and hope to welcome you back for another memorable experience soon!
Our driver Pietro was an excellent driver. Our tour guide Antonette was very knowledgeable and cordial,
Response from Host, Aug 2025
Thank you for your kind words!
We’re so pleased to hear that you had a positive experience with us. We're especially glad you enjoyed the journey with Pietro, who is indeed an excellent and experienced driver, and that Antonette made the tour even more enriching with her knowledge and warm, friendly approach.
Your feedback means a lot to us, and we hope to welcome you again soon on another unforgettable adventure!
Artur and Monica are the best!! I can’t recommend this tour enough! Please
Do it. Totally worth it. They are attentive and very informative. I am so glad I did this tour!
I was sick the day of my original tour reservation. They worked with me and rescheduled my tour for the next day! I’ve used this company many times in many cities. Always a good experience!!
Response from Host, Aug 2025
Thank you so much for your wonderful review and continued trust in Welcome Italy!
We’re delighted to hear that Artur and Monika made your tour informative and enjoyable, and that we could accommodate your rescheduling with ease. It means a lot to us to know you’ve had great experiences with us across many cities.
Your heartfelt recommendation truly warms our hearts, and we look forward to welcoming you again on many more unforgettable tours!
Warmest regards,
The Welcome Italy Team
Amazing tour! So happy to get out of the city and enjoy the beautiful countryside of Tuscany! Do not hesitate to book this tour! Interesting, fun, and incredible tour guide Monica! Perfect day!
Response from Host, Aug 2025
Thank you so much for your amazing feedback!
We’re thrilled to hear that you had such a perfect day exploring the beautiful Tuscan countryside it really is a special escape from the city. Monika will be so happy to know she helped make your tour interesting, fun, and unforgettable!
Your recommendation means the world to us, and we hope to welcome you back soon for more incredible experiences in Italy.
Warmest regards,
The Welcome Italy Team
Our guide Juliana and driver Artur did a tremendous job. The tours of Siena and San Gimigano were excellent. We were given great information. The wine tasting at Tenuta Torciano was fantastic!
Response from Host, Jul 2025
Dear Guest,
Thank you so much for your kind words!
We’re truly delighted to hear that you had such a great experience with Juliana and Artur they’ll be thrilled to know their efforts made your day memorable. Siena and San Gimignano are such beautiful destinations, and we’re glad you enjoyed the insights shared along the way.
We’re also happy to hear that the wine tasting at Tenuta Torciano was a highlight of your tour , it’s one of our favorite spots too!
Thank you again for choosing Welcome Italy. We hope to welcome you back soon for another unforgettable experience in Italy.
Warm regards,
Two wonderful cities to see and explore. Especially Sienna which is far too big to see in the time allotted. Wish we could’ve skipped the wine tasting and spent more time in Sienna! But when in San Gimignano you have to try the gelato near the outside market just up from the gate. Too die for!
Response from Host, Jul 2025
Dear Guest,
Thank you for sharing your experience with us! We're so glad you enjoyed exploring Siena and San Gimignano two truly unforgettable cities full of charm and history.
We understand your wish for more time in Siena; it certainly has so much to offer and can’t be fully appreciated in just a short visit. Your feedback is valuable and will help us continue refining our itineraries to better match our guests’ interests.
And yes the gelato in San Gimignano is absolutely a must try! We're happy you got to enjoy that sweet highlight.
We hope to welcome you back again soon for more discoveries in Italy!
Warm regards,
The Welcome Italy Team
It is a long trip, please use sport shoes and comfortable clothes.
Bring water and be prepared to enjoy.
Response from Host, Jun 2025
Thank you very much for your kind review and thoughtful advice. We are pleased to hear that Julianna and Luigi contributed to making your visit to Siena and San Gimignano a memorable experience. As you mentioned, it is indeed a long journey, and we appreciate your helpful suggestions for future travelers. We look forward to welcoming you again with Welcome Italy
Amazing experience. Theresa was great! She was very knowledgeable and guided us to wonderful stops and spots on our tour. She was excellent and engaging with our children as well. Sienna and San Gimignano were both beautiful and we had a good amount of time in both. The winery lunch and tasting was amazing as well with great wines and views. The owner was very friendly and welcoming. We had a great time and would definitely strongly recommend the experience.
Excellent tour with Dina and our driver, Pietro! Dina is extremely knowledgeable and personable, and was very kind to let us stop for breaks or quick shopping when we saw something we wanted. She was very clear in her instructions regarding meeting points and times. Overall and excellent day with an excellent guide!
Teresa was our guide and Pino was our driver. We enjoyed both of them, and they made the trip very enjoyable.
We really liked Sienna and Teresa gave us a lot of background on the area. We then went to San Gimignano for a wine tasting and lunch. They treated us very well there and the food kept coming. This, too, was enjoyable.
We left hotel around 6:30 a.m. (they picked us up at 2 hotels) and returned around 6:00 p.m.
It was a wonderful day and very glad to get out of the congestion in Rome.
Our guide Monica and driver Natalia made this experience truly memorable. They were both knowledgable, courteous, friendly and totally helpful. This itinerary is amazing and the two ladies ensured that the day was wonderful
Joseph (Jessippi) and Roberto took us to Sienna, San Gimignano and to the Tenuta Torciano winery. The most rememberable and most cherished part of this trip was when we met the owner and his family at the Tenuta Torciano winery. We had seen them and this winery on U-Tube videos and were so excited that we had an opportunity to meet them. Joseph shared much knowledge about this region and winery with us. My wife and I had just finished a 9-day Mediterranean cruise that started in Barcelona and ended in Rome, and we both have to say, without a doubt, that this tour was the highlight of our vacation.
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