Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.
From the operator’s live schedule on Viator, checked Oct 7.
Start you trip form Siena at Via Giuseppe Garibaldi 72, where you will meet our driver. You will travel by minivan to reach the first point of interest.
Castellina in Chianti enchants with its historic allure, surrounded by picturesque landscapes and tantalizing Tuscan cuisine, offering a timeless escape into the heart of Italy. Admire the medieval Rocca and the church.
Enjoy a wine tasting in an evocative winery in the Chianti area.
Enjoy a free visit of Monteriggioni city inside the walls. The castle of Monteriggioni dates back to the second two decades of the 13th century and was founded by the Republic of Siena.
Enjoy a wine tasting in which you can taste the famous Chianti wine typical of this area surrounded by a beautiful landscape.
Return back to Siena on board off the minivan and the driver will drop you off at Via Giuseppe Garibaldi, 72.
Reviews collected by Viator and Tripadvisor
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For a full refund, cancel at least 24 hours before the scheduled departure time.
Chianti and Castles Tour from Siena Small Group lasts about 5 hours. The itinerary has 6 stops.
Prices start at $97 per person for this Siena experience, booked through Viator with the price shown before checkout. There are 2 booking options, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day, starting at 1:00 PM and 2:00 PM.
Children aged 3–12 pay from $49, adults from $97. Infants go free.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is Meet our driver in front of Hotel Minerva. Hotel pickup is not part of this experience.
The experience is available in EN, IT, ES.
It is a small-group experience with a maximum of 8 participants.
Infants and small children can ride in a pram or stroller
Yes, bookings are confirmed instantly.
Travellers rate it 3.6 out of 5 across 7 reviews on Viator and Tripadvisor; it is run by MyLuxuryDrive.
Reviews collected by Viator and Tripadvisor
The tour van was old and aircon not working in both vans- in winter not an issue but with 36C heat every one complained about how hot we were Also quite rushed at venues to keep to time schedule for wineries That said country side was beautiful - guide pleasant and wineries interesting
Really enjoyed this tour! Although we had difficulty locating our driver, once we did we had a great tour including two wineries, both were fantastic, followed by stops at two towns with an hour free time for each. We also had two stops for photo op’s with one of the two being the most gorgeous views. A lot packed into a half day trip and looking forward to doing it again. Highly recommend.
Great afternoon tour. A nice balance visiting two medieval sites and two wineries. Our whole family enjoyed. Friendly and knowledgeable driver. I would recommend!
Overpriced! Two five minute roadside stops to take pictures, two 20 minute stops without the guide to wander around small hillside towns, ( one after dark), two very long wine/ oil / balsamic tastings at wineries encouraging us to buy their produce. The ' Tuscan delicacies' were two slices of mortadella and some scraps of toast. Essentially a wine promotional tour
Dear guest, Thank you for your review. Kindly note that in the description you don't find the voice "snacks". You don't find in the inclusions anything like "light lunch" or "food tasting". You can see only the wine tasting, it's up to the winery to give you some dry snacks with the wine like bread or grissini. Best wishes, My Luxury Drive Team Best wishes, My Luxury Drive Team
The wines we tasted at the two wineries, Antinori and Ai Laghi, were wonderful. However, the Antinori room was so noisy that we couldn't hear the speaker very well. In addition, the Italian snacks there were sparse - no bruschetta, no cheese, no prosciutto, as cited in the tour description.
Dear Carol, Thank you for your review. Although, you don't find bruschetta, cheese or prosciutto mentioned nor in the description nor in the inclusions. You only find only wine tasting or dry snacks.
This was supposed to be a small group tour, the ride was small group but at the wineries it was a group of over 20! Not the small group as advertised.
Dear, Yes, it's a small group tour since you don't share the driving with over 20 people in a bus but you drive in minivans. The wine tastings are together indeed it's not advertised as private wine tasting but as a shared tour. Best wishes, My Luxury Drive Team
The trip was great! Especially our driver Daniel who was very knowledgeable and fun to be with. We enjoyed the whole trip immensely and would do it all over again!!!
Hi Joseph, I would like to thank you for the review, we are happy that you enjoyed the tour. Best wishes, My Luxury Drive
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Chianti and Castles Tour from Siena Small Group | 5 hours | 3.6 (7) | $97 | |
 Hidden Castles & Chianti Wine Experience– Small Group | 5 hours | 4.5 (184) | $56 | View |
 San Gimignano, Chianti, and Montalcino Day Trip from Siena | 11 hours | 4.3 (154) | $177 | View |
 Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle | 1h 30min | 4.7 (133) | $67 | View |
 Small-Group Chianti and San Gimignano Sunset Trip from Siena | 8–9 hours | 4.8 (67) | $217 | View |
 Siena: Chianti Sunset Tour with Dinner & Wine Tasting | 3 hours | 5.0 (58) | $109 | View |
 Siena Small group Cooking Class in a Chianti Farm | 3h 30min | 5.0 (20) | $92 | View |