San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Such a great day ! Highlight of our trip! Lovely smalll towns, scenery, wonderful wine and lunch experience!!!great tour guide! His name was Frederic! Highly suggest this trip!

Excellent guided road trip covering major parts of Tuscany like San Gimignano, Monteriggioni, Chianti and Siena. Our guides Martha and Louisa had very good knowledge and patiently explained the details of each of the places that we visited and our wonderful driver Carmine took us through the most scenic routes that felt no less than Asciano and Vale D'Orcia. The lunch with wine tasting was an experience a kind and it had a good spread of appetizers, main course and dessert along with at least 4 to 5 types of wine tasting. Dining with people all over the world, it's an unforgettable experience that we shall cherish for a lifetime. This tour is not only must do for nature lovers, but also a value for money experience for all those who want to do a roadtrip in Tuscany, but are not comfortable in driving seat to the left of the car or hesitant to pay 400-600€ for 8 hours of hired car service with chauffeur, and lunch extra. Lastly, if you take the trip, please listen to the recommendations of the guides for the best Gelato in Tuscany at San Gimignano (Dondoli) and best coffee shop at Siena (Nannini) if good food is your pick. And do try everything given in the winery💓💓

Great trip through the hill towns with Ricardo and Stella. Trip to the winery was wonderful- our guide there was great

Such a nice experience, the tour guid, Ricardo was so informative and friendly. Siena is the city must see.

A great day seeing the medieval cities .. and a delicious lunch at the winery with plenty of wine to taste and enjoy. Well organised and plenty of time at each place. More walking than I envisaged, as buses have to park outside the city centres, so be prepared for this. Our guides Ricky and Christina were great…and very helpful to me when I had to take it a little slower due to a recent injury during my travels. Great value for money.

We had notice a day before one of the stops was cancelled due to a festival. Meeting our group at the bus was easy enough. We were informed how our day would go and we set off to our destinations. The stops seemed a little long on free time and the day was long. Our guide Michael, and the others did well to keep our group together and on time. The stops were beautiful and interesting.

We had an amazing day with Lily touring multiple different places throughout Tuscany. I can’t say enough about how great Lily was to work with and how fun she made the day. I would highly recommend this Danny one that’s considering it.

Lily was a great guide. Amazing day well managed and plenty of free time in each location. It is a big day so pace yourself

It’s lovely. But it’s a packed bus. The sights and the medieval towns were lovely. The lunch at the winery was lovely but the tour of the winery is basic.

Amazing way to know more about the smaller medieval towns in Tuscany. Millie, our tour guide, was knowledgeable and entertaining. This tour is a must for gamers who played AC II.

Sandro was a very Nice guide, pontual and funny, keeping the group well organized

Sandro ensured we had an amazing experience. He was clear with his instructions and made sure everyone was accounted for after each stop. The whole trip was fabulous with the wine tasting and lunch an absolute highlight! We loved ‘Winestein’. Grazie Mille!

Sandro was amazing guide, pontual and funny.

Had a great experience with Sandro! So knowledgeable of the area and very personable.

Sandro was an excellent guide we had a wonderful tour and experience!!

We had a fantastic day with our guide Marta and our driver Enrique. Marta was incredibly informative, knowledgeable and friendly, and really helped make the whole day enjoyable and stress-free. She was very clear with her instructions, explaining exactly where and when to meet at each meeting point and how long we would have in each location. We had ample time to explore everywhere without ever feeling rushed. Our favourite stop was San Gimignano, which was absolutely beautiful. Marta also recommended lots of things to see and do in each place, as well as great suggestions for where to eat and drink. She even pointed out some beautiful viewpoints that we would probably have missed without her local knowledge. Lunch at a local vineyard was also a real highlight. The food was delicious, the portions were huge, and they were very accommodating of dietary requirements. We were able to taste four different types of wine, and you could ask for more if you wanted to try additional wine. It was a lovely, relaxed setting and added something really special to the day. Enrique was also a fantastic driver, making the journey between each destination comfortable and easy. A brilliant day from start to finish. Thank you Marta and Enrique for making it such a memorable experience! We would definitely recommend this tour to anyone wanting to explore Tuscany. ❤️

Absolutely fantastic day trip from our Florence base. The tour was extremely well organised from start to finish. San Gimignano, Siena and Monteriggioni were all great to see, and having a knowledgeable guide made each stop so much easier. We particularly enjoyed being able to explore the towns without having to worry about transport or logistics. The lunch and wine tasting were also excellent - great food and some fantastic Tuscan wines. The whole experience felt relaxed and enjoyable rather than rushed. Our guide, Marta, was amazing - so friendly and knowledgeable, and did a great job keeping the group engaged throughout the day. If you’re visiting Florence and want to experience some of the best of the Tuscan countryside in one day, I would absolutely recommend this tour. Well worth it!

perfect guide, and tour course Thanks a lot to Marta!

I really enjoyed this trip and it was a nice break from being in the city. It's a typical bus tour where everyone piles on from one stop to the next, but it gives you a great opportunity to visit some interesting sites. All the stops were great, including lunch at a vineyard with wine tasting. However, Siena was probably our favorite stop. Beautiful city and full of energy as the city prepared for the upcoming Palio di Siena horse race.

This was such a fun day trip through the Tuscan region, with wine tasting, a delicious lunch, and plenty of beautiful scenery along the way. The highlight for me was definitely spending the afternoon exploring Siena. A great way to experience the best of Tuscany in one day!

The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!

Excellent tour. Special thanks to our bus driver, Alice, and tour guides Fabi and Louisa. Cathedral in Siena worth paying extra. Beautiful scenery, tasty food and wine, shopping lover's dream. Grazie!

Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!

I had a good time. The tour was efficient, with minimal waiting time and a good balance of time allocated to each segment. Thank goodness for the air-conditioned bus ride. The driver Gabriel and guide Fabi were excellent. Fabi was knowledgeable and articulate in both English and Spanish, which made the trip enjoyable.

This is a great tour. We went to the medieval museum and a torture museum in San Gimignano, both were free. Look up each town ahead of time or while on the bus to see what you want to do. Lunch was a great time.

Excellent way to see and experience multiple Tuscany cities in one day. Winery was nice, but simple. Somewhat long day and requires uphill walking.

This was wan excellent day tour and value for money. The check-in process was seamless. The guide (fabi) and driver (Giovanni) made the experience so enjoyable. The three towns are a must see. The lunch and wine tasting was amazing and very informative.

I am writing this to warn other travelers: **Do NOT trust your vacation or your money with Caf Tour & Travel.** My family and I arrived promptly at 8:00 AM for our tour to Siena and San Gimignano, only to be left in the lurch. We were not alone; several other passengers were also left stranded at the meeting point with zero explanation. The lack of professionalism that followed was even worse than the logistical failure: * **Blatant Avoidance:** They completely ignored our urgent text messages. * **Hung Up On Me:** When I finally got through to them on the phone to resolve the situation, the representative disconnected the call on me** the moment I explained we had been left behind. It is one thing to have a scheduling error; it is quite another to show such cowardice and a total lack of accountability. They took our money, ignored our presence, and then literally hung up on us when confronted. We have been forced to scramble and navigate public transportation ourselves just to save our day This agency is unreliable, unprofessional, and clearly has no regard for the families who book with them. Save yourself the stress and book with anyone else in Florence.

Tour company was very solid. Kept things moving on time. Bus was comfortable, but not a lot of legroom for a person who is 6'1". The winery was WEAK! Food was decent, but the wine was not particularly good. Also was direct to consumer scheme, so pretty hard sell to the point we're they offered to set up a wine tasting in our home in the States (think Tupperware party). Pretty off putting. Also, facility was industrial, not your picture of a wine estate in Tuscany.

Martha was the host, she was great! She always had lots of info for each place we visited. Such nice towns we visited. Love the area! Would recommend the tour.

The tour was very well organized and managed by Sandro who led the group through the history of this part of the Chianti region. He was very knowledgeable & pleasant. The lunch was delicious & accompanied by tasting of 2 types of Chianti wine & a vin Santo. Lucia, the guide to the Siena cathedral, was excellent & very thorough

Overall: Great destinations, great guide, poor lunch, too many people. Great tour guide, very friendly. Fantastic locations. Too many people for it to be personal at all. It’s a full double-decker Coach bus completely filled with people. If you get stuck sitting in the back of the bus, you have to wait for everyone else to get off first which wastes time at each location. Felt like a hierarchy of seating arrangement. Winery lunch was mediocre. Winery was not spectacular. They turn over hundreds of people a day and the food was basic. Lots of yelling to explain each wine.

Just a nice time. Constantino ( I believe that was his name) was informative, passionate and funny. Much Enjoyed lunch and wine in Tuscany winery. The only (small) issue I had was the tour had English and Spanish translation. You should separate the 2 audiences (thought Constantino handled it well!)

Great experience and easy way to get out of Florence for the day to see other areas of Tuscany. It was well organized even for a large group. Lunch was great with the wine tasting and seeing medieval villages was just amazing.

We had a great experience on this tour, thanks to our guide Jakopo and driver Raul. Jakopo was polite and very informative, sharing lots of interesting facts about Tuscany throughout the day. He also gave clear instructions about meeting points and times, which helped everything run smoothly. Raul, our driver, was equally professional and ensured we arrived safely at each destination. Our first stop was Monteriggioni, a charming little town where we had about 30 minutes—just enough time to grab a coffee and take in the atmosphere. We then spent around three hours in Siena, which felt like plenty of time to explore the historic streets, enjoy a delicious lunch at a local restaurant, and pick up a souvenir. After Siena, we stopped at Poggio ai Laghi for a wine tasting experience. We sampled four different wines, two types of balsamic vinegar, and a selection of bread and cold cuts—definitely a highlight of the day. Our final stop was San Gimignano, where we had 1.5 hours. While we enjoyed exploring this beautiful hilltop town, we would have loved a bit more time there, as it felt slightly rushed compared to the earlier stops. Overall, it was a well-organized tour with a good mix of cultural exploration, food, and relaxation. Highly recommended for anyone wanting to experience the best of Tuscany in a day.

The tour was good. We got to see a few different towns and got some lunch and wine as well. I loved Siena, skip the walking tour and see the cathedral and main square yourself. Definitely don’t have enough time to enjoy it all. Overall, it was a great tour and Marta was amazing!!!

We enjoyed the trip very much. We left Florence on time and returned as scheduled. The time in each city was more than enough to walk and see the main attractions. The visit at the winery was very pleasant, first we tasted two types of spumant wines and learned more about the winery, then we had a three course meal paired with three different Chianti wines. Our guide Marta was very nice, friendly and shared a lot of information with us about the trip and also gave us very clear information about meeting points, attractions we should see and places to shop or have a gelato. The driver Giovanni was very nice, we had a smooth drive. They both deserve a five star. All in all we spent a very nice day and we were pleased with the CAF Tour and Travel tour operator.

Sandro went above and beyond. He loves his work and it shows. The information provided was perfect. The tour itself was great definitely worthwhile. Sandro really went out of his way to help me since I wasn’t able to walk alot

Great time, Marta and driver were excellent. Would recommend this tour. Had a great time. Just a long day.

I signed up for this tour (Viator)months ago and the tour was advertised as a small group (English) and it would end at about 2. But it seems that that is not what the tour provider (3rd party) was offering. What we got is about 80 people English/spanish an all day event. Got back at about 8:00pm. The guides (Marta and Hilaria) did a great job but it was not what was advertised on Viator site. Very disappointing. I have used Viator for years but this was, sadly, the worst experience.

It was so organized and so well planned! Our guides were informative and friendly, but mostly charming. This is a nice mix of walking and riding, the wine tasting and lunch was fabulous! Don’t miss this tour.

this was a very enjoyable tour. Our guide was excellent. The winery tasting and lunch was delicous.. Highly recommend this tour to everyone, especially wine lovers.

Organized and positive vibe, so friendly guide Elizabeth ! We enjoyed the full experience with enough time in each place

If you are a bourbon hunter, you'll be surprised by what you can find on this excursion. If you are a Scotch hunter, you, too, may be surprised by what you can find on this trip. Not gonna say what. Definitely not gonna say where. This isn't a joke. Now that I have your attention..... This was a nice excursion. Glad I didn't have to drive to these places. Tight roads with pedestrians and bicyclists the closer we got to the little villages. We still got lots of steps in exploring these places. We enjoyed some delicious Gelato. There are some breathtaking vistas. The highlight for me was the wine tasting and lunch. We have done dozens of wine tastings at home. They were nothing compared to the first-rate explanation and coaching we received here. There was also basalmic vinegar experience. Would you ever think to pair vinegar with ice cream? I hadn't but I am gonna give it a shot now! Also gonna try it with strawberries. Of the villages we visited, I enjoyed Siena a lot. Lots to explore. The piazza where they hold the horse races is a wonder to behold! Gordon Breckenridge's works are worth checking out. Just know Siena is much more pricier than other places. A beer, a spritzer, and an espresso = 20€. Not complaining, just saying. Our guide was Riccardo. He was knowledgeable and interesting to discuss Italian history with. Our driver was Rudolfo. He got us in and out of some tight spots quite skillfully. My one complaint is the gathering point at the start. There were four other companies and tours gathering at the same time in the same area. The companies were all dressed similarly, too. It was a very confusing time because people invariably got in the wrong que only to find out their tour was somewhere else. It was a stressful time at the start. Overall. I WOULD definitely do this again. If we return with our family, it was a nice way to get out of Florence and see the "real" Italy. There were 52 people on our tour and we still had plenty of time to see and do what we wanted. The large group we were with was respectful of each other's time and space. The bus had two doors making entry and departure very seamless. We'll worth the price we paid.

This tour helped us see three towns when we had a short few days in Florence! Our guide Fabi was fantastic and walked us through each area carefully. We had insight into each area and a lovely wine tasting with a small accompanying lunch. Best part was the starters and tasting the chanti wine! I highly recommend this tour for seeing the most in a day and for value❤️

Our tour guide Aaron was awesome!!! Very patient and informative!!! The winery was awesome!!! Loved the food, wine and our host! Our tour guide in Siena was very nice but talked too fast so we couldn’t understand a lot of her tour. Overall, loved the day!!!

Nice Sienna and San Gimiliani Good Gide and excellent driver Carmine Wine testing well organized Nice cianty

What a great day! Marta was a great tour guide, and Sergio, a very smooth driver. Siena and San Gmignano are beautiful of course. We did not read the fine print that Montereggioni is basically closed in the winter so we did not go there. They were nice enough to drive a bit out of their way to allow us to take a picture of the town.

Comfortable commute, spectacular scenic views! The best part that I like was that they also gave us a free time where we can roam around and cobble stone streets and look at local shops! We enjoyed local restaurants and the food was unbelievable! So good!