Siena And San Gimignano From Rome: Wine Tasting Tour In Tuscany

Sam and Luigi helped make our first trip to Tuscany perfect. They were knowledge, personable and provided a great day for us.

Our tour guide “Sam” was beyond informative and just a delightful person. So patient and sweet. We really were fortunate to have him. What an amazing day. If I could change anything… I would like less time in Siena and more time in San Gimignano for shopping 😄

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.

Such an amazing day trip to Tuscany! Long day but worth it. Monica was an amazing guide and so friendly and informative. Our driver was great as well. The highlight was lunch at the winery, amazing experience. Highly recommend booking if you are looking for a quick trip to see Tuscany.

Very much enjoyed our day! Tour guide and driver were very kind and helpful. We and our grandchildren learned a lot about the places we visited.

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!

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.

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.

We had the best time as a couple who enjoy wine and also wanted to see Sienna and San Gimignano. Pro top at San Gimignano go the very top of the castle and look at the views of the countryside. Our guide was great taking us around and then letting us explore each city. Once we were done, we headed to a beautiful winery where we had a three course meal filled with laughter, wonderful homemade dishes and of course 8-10 different wines. Our guides picked us up, dropped us off and stopped for coffee and breakfast in the morning. It is not a guided tour through the towns but you walk and explore on your own and then get o enjoy the best lunch and food. The lasagna with the truffle oil was the best and then they had the most delicious braised beef and potatoes served with the top of the line wine. Just got do it. It’s so worth it

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

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!

great service! we were picked-up from our hotel early morning (right on time!) and stopped for a coffee right outside of Rome. everthing was great! our guide (Giuseppe) was a fountain of knowledge and Constantino, our driver, performed also as a great DJ on our way back to our hotel. though heavy rain, we got to see both towns and had a great lunch including a wine tasting experience at Tenuta Torciano. very nice Sunday!

Ease of use to see other parts Italy. Drivers professional safe. Tour guide very knowledgeable, friendly, helpful. Thank you

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.

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!

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.

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.

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!!

Really enjoyed our day trip from Rome to Tuscany! It was just 2 of us so I was happy they didn’t cancel. Would highly recommend!

Absolutely amazing. Great views of the medieval towns. Got to taste all kinds of wines. The meal at the end is spectacular too.

Such a beautiful trip through Tuscany!! Small group was the very best way for us !! We felt each moment was planned to give us the best experience! Joseph was so good !! He was witty & knowledgeable & gave us a great pace for the day! We never felt rushed, he gave us a dreamy peek into both Siena & San Gimignano, as well as the gorgeous Tuscan countryside! Our driver Mr. M was so professional in his demeanor & dress and extremely polite & respectful He was at top of list of our favorite drivers! We felt so pleased to have such a reliable & trustworthy guide & driver. They went above to communicate with us prior to the experience & made us feel like we were among friends with everything handled so well , Big big thanks from your Texas friends !! Delightful day, thanks to you both !!

Amazing tour. Our guide, Stephano, was amazing, very knowledgeable and sweet. The wine testing was incredible.

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

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.

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!

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!

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.

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

Our driver Pietro was an excellent driver. Our tour guide Antonette was very knowledgeable and cordial,

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!!

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!

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!

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!

It is a long trip, please use sport shoes and comfortable clothes. Bring water and be prepared to enjoy.

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.

The journey, visit to the towns of Siena and San Gimignano are definitely etched in our memory. Special mention to tour guide Dina and driver Roberto, who made the journey very interesting, pleasurable and safe.

Wonderful, intimate experience! Our guide Monika and driver Adam were both outstanding. And the Tuscan food, wine and views! Highest recommendation possible from us!

Severino was welcoming and very knowledgeable explaining history and culture. He accommodated me to walk at my pace and stop for a brief rest as needed. The tour was interesting & Severino answered all questions. The driver Maximo was excellent providing a smooth safe ride, opening doors and always being prompt to meet us. The lunch & wine tasting was superior and provided awesome landscapes to take photographs.

Daniella was very professional and did an excellent job driving us to the different sites. We enjoyed chatting with her and sharing life experiences.

Wonderful experience! We loved every minute. Theresa, was very polite and incredible knowledgeable all the way. Thank you for also being the best guide and help with my family.

We were pleasantly surprised to see we had a private tour in a sleek BMW. Our driver Luigi was excellent and our tour guide Fabio looked after us. We had an early start so we stopped for breakfast. He made sure we tried local delicacies. But the highlight of the tour was the wine tasting with lunch. Perfect!

Even in the rain, we very much enjoyed our tour. Our small group ended up being just my husband and I. The two Tuscan villages were stunning and the wine tasting was a dream. This was our favorite tour of our time in "Rome". We're so glad we got out of the city for this relaxing beautiful tour of the Tuscan countryside.

The views we experienced during our all day trip were amazing. Our guide, Josh, was extremely knowledgeable about the entire region and was able to give us the history of area, as well.

Everything!! Our guide Teressa was great!!! She gave us do much information and free time! So enjoyable!! Our driver Max was also so accommodating! Great tour!!

We had the best time with Giuseppe and Claudio was such a great driver. Everything was so special about the whole day. Would do it again in a minute I highly recommend it. Those two were the best.!!! Coming back next April for them to take us somewhere else!! ❤️