Hidden Castles & Chianti Wine Experience– Small Group

Badge of Excellence

Siena, Italy

Popular pick

Booked 10+ times last week!

5 hours (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

4.5

· Raquel_D ·

Apr 2026

Such a beautiful day in Tuscany! The views were incredible, the wines were amazing, and everything was perfectly organized. Highly recommend! We had an excellent tour guide (Val) and driver (Dontorel).

· Steven_S ·

Mar 2026

The 2 wineries visited were both very nice…the wine at the 2nd (along with the balsamic vinegar) was exceptional. 2 historic site stops in addition made this a complete experience. Actually compared to some tours this felt like a great value!

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Overview

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

Sip at two wineries with an expert multilingual guide
Scenic Tuscan countryside views provide a picturesque backdrop
Free time in Monteriggioni lets you explore a charming medieval village
Ideal for wine lovers looking to enjoy authentic flavors

Sample Menu

Starter

Bread with Olive oil

Starter

Bruschette

What's Included

Travel by air-conditioned minivan or minibus
Two wine tastings in Chianti
Alcoholic Beverages

Tasting of 7 wines in total
Wine, Olive oil and balsamic vinegar sampling
Snacks

Local products tasting (bruschette, salami, cheese)
Expert multilingual tour leader and driver-guide
travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.

Gratuities

Meeting and Pickup

Meeting point

Siena FS
53100 Siena, Province of Siena, Italy
Start your trip outside of Siena Train Station (Ferrovia), where you will meet the guide. You will recognize them by their green shirt.

End point

This activity ends back at the meeting point.

Itinerary

Your tour of the Chianti wine region in Tuscany starts with a hotel pickup in Siena. When you’re picked up, hop aboard an air-conditioned vehicle with your small group as your guide drives you through the countryside. Take in the views along the way to the first winery.

Sample wine paired with complimentary snacks while you learn about this winery’s winemaking process. Your tour guide at the winery takes you to the cellars and tells you the secrets behind the types of wines they serve, including a popular Merlot and Cabernet Sauvignon.

After the first winery, the town of Monteriggioni is up on the agenda. Spend some free time wandering around the village or visit the castle if you choose (own expense). It’s been said that the cafes in the town also serve a delicious coffee if you’d like to get off your feet for a while.

Last up is another Tuscan winery. Here you can taste some more wine and also oil before getting back in your car fir the ride back to your hotel.

Siena

30 minutes • Admission Ticket Free

Castellina In Chianti

1 hour • Admission Ticket Free

Fattoria Lornano

1 hour 30 minutes • Admission Ticket Free

Strada Statale 222 Chiantigiana

1 hour • Admission Ticket Free

Monteriggioni

30 minutes • Admission Ticket Free

Siena

30 minutes • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Stroller accessible
Near public transportation
Infants must sit on laps

Infant seats available
Most travelers can participate
Customers must be able to climb and descend stairs.
Please note that during low season from November 16th to March 14th Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough passengers to meet requirements (4pax are required). In the event of this occurring, you will be offered an alternative or full refund
This tour/activity will have a maximum of 15 travelers

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Cancellation Policy

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

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Kimberly_R

We had such a wonderful time on this tour! Valesca and Luigi were the best! Valesca speaks fluent Italian, English and Spanish and was extremely pleasant and kept the group running on time. The wineries were excellent. The two towns were amazing. Luigi was a fantastic driver who kept us all safe. I recommend this tour!

Reviews

4.5

based on 174 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

The experience was nice....

Raquel_D, Apr 2026

Response from Host, Apr 2026

Dear Customer, Thank you for your feedback! We’re glad you enjoyed the day in Tuscany and that the guides made your experience special. We appreciate your recommendation and hope to see you again soon. Best regards, my Tour in Italy

A great and varied afternoon not soon to be forgotten

Steven_S, Mar 2026

Response from Host, Mar 2026

Dear Customer, Thank you for your feedback! We’re so happy you enjoyed the wineries, especially the wine and balsamic vinegar at the second stop. It’s great to hear the historic sites are added to the experience too. Best regards, my Tour in Italy

Great guided experience with Luca

Christina_P, Nov 2025

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Response from Host, Nov 2025

Dear Customer, Thank you for sharing your feedback with us! We’re delighted to hear that Luca provided such knowledgeable guidance and helpful restaurant recommendations. It’s wonderful that you enjoyed the wineries, the cities, and the stunning Tuscan views. Your feedback means a lot to us, and we hope to welcome you again soon for another memorable tour! Best regards, My Tour In Italy

Tour host was extremly...

Jeremy_P, Oct 2025

Tour host was extremly knowledgeable and created a friendly atmosphere on the mini-bus. The 2 wine tasting experiences were excellent, but contrasting. One being more of a family vine yard located on an old Tuscan farm in the hills, the other being a dedicated tasting / function venue, hosted by a charismatic Sommelier. Quality of wine superb and from my hazy memory exceeded the 7 glasses advertised! Only down side was disorganised pick-up at station. Having a wine tour notice on bus and having host there at stated meet time, 15 mins before departure. Italian speaking driver turned several clients away before host arrived. Still a 5-Star tour though, as rest of afternoon made up for this.

Response from Host, Oct 2025

Dear Customer, Thank you for sharing your feedback with us! We’re glad you enjoyed the wine tastings and the tour host’s knowledge and friendly atmosphere. We apologize for the disorganized pickup and will work to improve this for future guests. We’re happy the rest of your tour was enjoyable and memorable! Best regards, My Tour In Italy.

Valeska was a wonderful...

Dane_H, Oct 2025

Valeska was a wonderful tour guide and both tastings were great! We had thought about going to a couple of vineyards on our own but it was well worth the little bit extra for the tour. I definitely recommend it.

Response from Host, Oct 2025

Dear Customer, Thank you for sharing your feedback with us! We’re delighted to hear that you enjoyed the tour and tastings, and that Valeska made your experience special. We truly appreciate your recommendation and are happy the tour was worth the extra. We hope to welcome you again on another memorable journey soon! Best regards, My tour In Italy.

You’ll have to get...

Emma_G, Sep 2025

You’ll have to get transportation to the meeting point. Make sure to wear walking shoes and check the weather. Guides are knowledgeable and friendly. Highly recommend for groups or even if traveling solo!

Response from Host, Sep 2025

Dear Customer, Thank you for sharing your feedback with us! We’re glad to hear you found the guides knowledgeable and friendly. Thank you for recommending the tour, whether for groups or solo travelers! Best regards, My Tour In Italy

Great tour

Camille_C, Sep 2025

It was a wonderful tour. Luca was informative and had a great sense of humor. The wineries we visited were welcoming and the tasting great. I highly recommend this tour.

Response from Host, Sep 2025

Dear Customer, We’re thrilled to hear you enjoyed the tour and that Luca’s knowledge and humor made it even better. It’s great to know the wineries and tastings met your expectations. Best regards, My Tour In Italy.

Relaxing and enjoyable experience in Tuscany.

Angie_B, Sep 2025

It was relaxing. Love our guide, don’t remember her name, a nice girl from Venezuela who spoke several languages, had a very engaging voice . The driver was nice and patient, nice little towns we visited. Delicious wine!

Response from Host, Sep 2025

Dear Customer, Thank you for sharing your feedback with us! We’re delighted you enjoyed the relaxing tour, the charming towns, the delicious wine, and our guide’s personality. We hope to see you again soon for another wonderful experience! Best regards, My Tour In Italy

Chianti wine tour so fun!!

Elizabeth_L, Sep 2025

The tour was fantastic! Loved both wineries and the stops in the villages. Worth every penny! Our tour guide was great.

Response from Host, Sep 2025

Dear Customer, Thank you for your wonderful review! We’re so happy to hear that you enjoyed the wineries, the village stops, and that you found the tour truly worth it. It’s also great to know that your guide made the experience even more special. We hope to welcome you back soon for another adventure with us. Best regards, My Tour in Italy.

Well organised tour with...

Kim_T, Aug 2025

Well organised tour with just the right amount of wineries and other experiences. 5 hrs went so fast! Met some lovely people on the tour from all over the world. Our leader was great.

Response from Host, Aug 2025

Dear Customer, Thank you for sharing your feedback with us! We’re delighted to hear you enjoyed the tour, the wineries, and the experiences, and that you met lovely people from around the world. We’re also glad you enjoyed your leader! Hope to welcome you on another tour soon. Best regards, My Tour In Italy.

Great tour of history and wine

Matthew_C, Aug 2025

Only about 30 minutes per town/castle, so if you want to climb the castle in the first stop do that first. But a phenomenal tour, great guide, and fantastic wine and snacks

Response from Host, Aug 2025

Dear Customer, Thank you for sharing your feedback with us! We’re glad you enjoyed the tour, the guide, and the wine and snacks. We appreciate your helpful tip about the time at each town and castle it’s great advice for future guests. We hope to see you again soon! Best regards, My Tour In Italy.

Very informative tour...

Sondre_T, Jul 2025

Very informative tour with a lot of good wine to taste. Stops in a quiet tuscan hilltop village, teo wineries and a medival castle.

Response from Host, Jul 2025

Dear Customer, Thank you for sharing your feedback with us! We’re thrilled to hear you enjoyed the informative tour, the fantastic wines, and the beautiful stops at the Tuscan hilltop village, wineries, and medieval castle. It sounds like a perfect day in Tuscany! We appreciate your review and hope to welcome you on another memorable tour soon! Best regards, My Tour In Italy.

Great Tour for sightseeing and wine tasting

Donna_W, Jun 2025

Great tour. The castles and the wineries were great. A lot of different wines to taste, but also gained knowledge of the region and the winemaking process. Just one warning. If you get car sick easily, make sure you bring your remedy. The roads are curvy and bumpy.

Response from Host, Jun 2025

Dear Customer, Thank you for sharing your feedback with us! We're glad you enjoyed the castles, wineries, and the variety of wines, as well as learning more about the region and winemaking. We also appreciate your helpful note about the road conditions it's great advice for future guests. We hope to welcome you again soon! Best regards, My Tour in Italy.

Great wineries, but very hot and uncomfortable

Damon_M, Jun 2025

Unfortunately broken air-conditioning made the van ride unbearably hot and sweaty—very uncomfortable for hours with a larger group of 14. Both wineries were great and were the saving grace for everyone!

Response from Host, Jun 2025

Dear Customer, Thank you for sharing your feedback with us! Thank you for your honest feedback. We’re sorry the broken air-conditioning made the van ride uncomfortable. We’re glad to hear the wineries were enjoyable and helped make the tour better.Your comments will help us improve our service. Best regards, My Tour In Italy.

Wonderful Experience Touring Wineries and Castles!

Kimberly_R, Jun 2025

Response from Host, Jun 2025

Dear Customer, Thank you for sharing your feedback with us! We’re delighted to hear you had a wonderful time on the tour. Valesca and Luigi will be thrilled to know they made your experience enjoyable and safe. It’s great that you enjoyed the wineries and the towns as well. We truly appreciate your recommendation and hope to welcome you again soon! Best regards, My Tour In Italy.

We enjoyed our trip -...

Ann_F, Jun 2025

We enjoyed our trip - there were 2 wineries and both were very different. The stop in the little town was ok. Just shops and walking around.

Response from Host, Jun 2025

Dear Customer, Thank you for sharing your feedback with us! We’re glad you enjoyed the two unique wineries. We appreciate your comments about the stop in the little town and will keep them in mind. We hope to welcome you again soon! Best regards, My Tour in Italy.

Both wineries had...

Katie_S, May 2025

Both wineries had excellent wine tastings with knowledgeable and friendly hosts. Our guide did a great job describing the Chianti region and history. The town and castle were highlights too.

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us1 We're so glad you enjoyed the wine tastings, the Chianti region, and the visit to the town and castle. It's great to hear our guide helped make the experience even more memorable. We hope to welcome you on another tour soon! Best regards, My Tour In Italy.

Amazing wine tour

Jacqui_C, May 2025

This wine tour is amazing , our guide was friendly and interesting We recommend a small group tour Great scenery great vino great day Not to be missed

Response from Host, May 2025

Dear Custmer, Thank you for sharing your feedback with us! We're thrilled to hear you enjoyed the wine tour, the scenery, and of course the vino! We're glad your guide made the day even better, and we really appreciate the recommendation. Hope to see you again soon! Best regards, My Tour In Italy.

We had an amazing...

Lori_W, May 2025

We had an amazing afternoon of touring the Tuscan region with Valeska as our fun tour guide and Mohammed as a very safe driver! The 2 wineries were informative and the guides at the wineries were interactive, personable, and taught us so much about wines. I would highly recommend this tour!!!

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us! We’re so glad you enjoyed your Tuscan tour with Valeska and Mohammed. It’s great to hear the wineries and their guides made such an impact! We’d love to have you join us again soon! Best regards, My Tour In Italy.

See more of Tuscany and enjoy its wonderful wines!

Sheri_S, Apr 2025

It was a wonderful opportunity to see the Tuscany countryside and taste wines of the region. Velasca is an informative guide who made the trip interesting and fun and Antonio drove us safely throughout our travels. Besides visiting two wineries we visited villages also. It was a very beautiful way to see more of Tuscany!

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us! We’re glad you enjoyed the Tuscany countryside, the wine tastings, and your time with Velasca and Antonio. We hope to welcome you back soon for more wonderful adventures in Tuscany! Best reagards, My Tour In Italy.

A fun afternoon stopping...

Elizabeth_R, Apr 2025

A fun afternoon stopping for two wine tastings and time to walk through 2 castle towns. Vatresca ( Our guide) and driver Marco were great. Tour started promptly. A great way to get a taste of Tuscany!

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us! We're so happy to hear you had a fun afternoon exploring Tuscany, with wine tastings and time to visit two beautiful castle towns. We're glad to know that Vatresca and Marco helped make your tour enjoyable! We appreciate your feedback and hope to welcome you again soon for another great experience. Best regards, My tour In Italy.

An afternoon well-spent

Margaret_B, Apr 2025

The tour was well organized. The group was not too big and I never felt I was being herded or rushed along. Guide Luca was very well informed on the history of the area and could switch back and between English, Spanish, and Italian with amazing facility. The Chianti countryside is absolutely stunning.

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback! We're delighted to hear that you enjoyed the tour and appreciated the organization, the smaller group size, and especially Luca’s knowledge and language skills. The Chianti countryside truly is a gem, and we're so glad you got to experience it! We hope to welcome you again on another adventure soon. Best regards, My Tour In Italy.

Wonderful Chianti winery trip

Janet_R, Mar 2025

Ale and Geovani were fantastic. They taught us a lot about he region were very friendly and made sure we all had a good time.

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us! We’re so happy to hear that Ale and Geovani made your experience memorable. It’s great to know that they were friendly, informative, and ensured everyone had a great time. We truly appreciate your comments and hope to welcome you again soon! Best regards, My Tour In Italy.

A charming and fun afternoon in chianti

Josie_H, Nov 2024

Lucas our guide was very knowledgable and the information he shared along the way was very interesting. Our driver was excellent and the minibus very luxurious. The two vineyards were charming and so much fun! Our only comment would be calling into the castle on the way back, at this time of year, was probably a mistake, it was dark and all the shops and bars were closed. Perhaps in the winter months the castle stop could be before the second vineyard. But all in all a fabulous and very enjoyable excursion. Highly recommend.

Response from Host, Nov 2024

Dear Customer, Thank you so much for your feedback. We’re thrilled to hear that you had such an enjoyable experience on the tour. It’s great to know that Lucas, our guide, provided you with interesting and valuable information along the way, and that you found both the driver and the luxurious minibus to be excellent. We’re also happy to hear that you had fun at the two charming vineyards. We truly appreciate your suggestion regarding the castle stop, and we’ll certainly take it into consideration for future winter tours. Your feedback helps us improve the experience for our guests, and we want to ensure that each stop is as enjoyable as possible. Thank you for highly recommending the tour, and we look forward to welcoming you on another excursion in the future. Best regards, My Tour in Italy team.

Unreliable and Unprofessional – A Complete Disappointment

osher_e, Nov 2024

I had a deeply disappointing experience with this wine tour. After booking and receiving confirmation, the guide never showed up on the scheduled day. We waited for over an hour, tried reaching out to the company multiple times, but received no response. We especially traveled by train to Siena for this tour, and they never showed up, which is very unprofessional. It completely ruined our plans and wasted our time. If you value your time and money, I’d recommend finding a more reliable tour operator. This experience was unacceptable, and I hope they improve their communication and accountability in the future.

Response from Host, May 2025

Dear Customer, Thank you for sharing your feedback with us! We sincerely apologize for the no-show and lack of communication during your tour. This is not the service we strive to provide, and we’ll work to improve it moving forward. Best regards, My Tour In Italy.

Beautiful views and great wines

Jonas_S, Oct 2024

Great tour and driver/guide. The only problem was that the sun had already set when we arrived in Monteriggioni, would have been nice to see in daylight.

Response from Host, Nov 2024

Dear Customer, Thank you for your feedback. We're so glad to hear that you enjoyed the tour and that the driver/guide made a positive impression. We completely understand your disappointment about arriving in Monteriggioni after sunset. It would have been wonderful to experience it in daylight, as the village is even more stunning during the day. We’ll certainly keep this in mind for future tours, and we appreciate your understanding. We hope the rest of your experience was enjoyable, and we’d love to welcome you on another tour in the future. Best regards, My Tour in Italy team.

Wine and tour!

Patricia_W, Oct 2024

Our guide, Vincenzo, was amazing! Knowledgeable, fun, patient and a great driver! He stopped for me when there was a great photo op and answered all of our questions.

Response from Host, Nov 2024

Dear Customer, Thank you so much for your fantastic feedback. We're thrilled to hear that Vincenzo made such a positive impact on your experience. It's wonderful to know he was knowledgeable, fun, and patient, and that he took the time to stop for those perfect photo opportunities. We’ll be sure to pass along your kind words to him. We hope to have the pleasure of welcoming you again for another great tour in the future. Best regards, My Tour in Italy team.

Nice day

Dan_B, Oct 2024

Enjoyable drive thru the countryside. 1 really good wine tasting at Poggio ai Laghi and an OK one at Lornano. Stopped at 2 very charming villages. Would have given 5 Stars but for our driver, Toto. He was very nice but gave virtually no information about anything, anywhere. So it all felt a tad bit aimless. Still, it was a nice day and we would recommend it.

Response from Host, Nov 2024

Dear Customer, Thank you so much for your feedback. We’re glad to hear you enjoyed the scenic drive through the countryside, as well as the wine tasting at Poggio ai Laghi and the charming villages you visited. It’s great to know you had a lovely day overall. We’re sorry to hear that the lack of information from your driver, Toto, impacted your experience. We always strive for a balance between comfort and informative guidance, and we’ll take your comments into consideration for future tours. We appreciate your recommendation, and we hope to welcome you again for another memorable experience with a more comprehensive approach next time. Best regards, My Tour in Italy team.

Definitely recommend this tour

Kevin_B, Oct 2024

Friendly and knowledgeable driver. We got to see the beauty of the Chianti region and enjoy a wine tasting. A very enjoyable experience.

Response from Host, Oct 2024

Dear Customer, Thank you for your lovely feedback, We’re thrilled to hear that you enjoyed your experience in the beautiful Chianti region and appreciated the service of our friendly and knowledgeable driver. It’s wonderful that the wine tasting added to your enjoyment. We hope to welcome you back for more memorable adventures in the future. Best regards, My Tour in Italy team.

Chianti

Joan_V, Oct 2024

Great time visiting Agricola Poggi ai Laghi in Monteriggioni & Mirco Pianigiani in the Chianti region. Our guide Marco was enthusiastic despite his broken English & played Frank Sinatra while we drove from Siena to Castellina in Chianti in comfy clean van. Unfortunately we had to cut visit to Monteriggioni short because of a huge electrical storm on the way back to Siena....all in all a fun afternoon! 🍷

Response from Host, Oct 2024

Dear Customer, Thank you for sharing your experience with us. We’re delighted to hear that you had a great time visiting Agricola Poggi ai Laghi and Mirco Pianigiani in the Chianti region. It’s wonderful that Marco's enthusiasm and the music made your journey enjoyable, even with the challenge of the electrical storm. We appreciate your understanding regarding the shortened visit to Monteriggioni, and we’re glad to know you still had a fun afternoon despite the weather. Furthermore, we hope to welcome you back for another memorable experience in the future. Best regards, My Tour in Italy team.