Siena Vespa Tour: Chianti Winery Visit with Tuscan Hills Exploration

Experience the beauty of the Tuscan hills on a Vespa scooter tour from Siena. Visit a Chianti winery, enjoy a wine tasting session, and savor a delicious lunch. Book now!

Duration: 6 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Chianti Road - Free time in Castellina in Chianti
  • Radda in Chianti - See Radda in Chianti during your ride
  • Casale dello Sparviero Winetour - A long avenue of cypress trees will lead you to the farmhouse, where you can have a wine tasting and take photos.
  • Monteriggioni - Free time in Monteriggioni
What's Included
  • Winery tour with Wine tasting
  • Helmet, fuel and taxes
  • Professional tour escorts and guide
  • Light Lunch made with typical fresh dishes
What's Not Included
  • Gratuities
  • Pick-up and drop off on request with an extra charge
Additional Information

Embark on a Vespa scooter journey through the picturesque hills of Tuscany, departing from Siena for a day trip. Your adventure also includes a visit to a Chianti winery for a delightful lunch! After getting acquainted with your scooter, you can decide to ride it solo or share it with fellow travellers (based on the option you’ve chosen). Under the…

Location
Via della Resistenza, 95
Via della Resistenza
If you have not selected the pick up and drop-off option, please meet our staff in Badesse.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.2
(130 Ratings)
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Jessica_p
Oct 14, 2025
Great day! - Getting to the start point was easy by taxi from the center of Sienna. Once there we met Fabio who took us through the formalities of the Vespa ride. After a few tries we decided that we weren’t super comfortable riding the vespas on the roads so he gave us another option, taking out a vintage Fiat!!!! What a blast!!!! My husband and I van both drive stick so we practiced in the lot first and then we were off! Such a fun day, Fabio was fantastic and took us to some great spots for photos and some history, then we ended at a winery where we tried some great wines. Super fun day!!
Review provided by Viator
Jon_s
Sep 1, 2025
We were told about this... - We were told about this by someone we met in the airport. We booked it a couple days before without any issues. We couldn’t get past the gate morning of unknowing there was a ring doorbell to use. Get there early as well to do a quick Vespa test. Overall the best time was had and would recommend to do again and again. Our guide was super and did a fabulous job of explaining history and the tour.
Review provided by Viator
Jenn_r
Oct 4, 2024
Vespa Via the Vineyards - BEST TOUR from Siena - If you like Vespas, Vino and Vineyards, this is not to be missed!!! Our guide was amazing, the tour was fabulous, the winery we visited was gorgeous, lunch and wine tasting were delicious and the little towns we got to tour were breathtaking. I highly recommend this tour company - it was epic and fun and so worth the cost! BUT beware, you must pass a Vespa driving test before you they let you go!
Review provided by Viator
Mariedle
Aug 28, 2024
Would go for it again - Nice tour. The Tourguide was nice and we all had fun. We were a group of 10 and got a bike for each couple. A must on your trip!
Review provided by Tripadvisor
Tisha_h
Jun 17, 2024
Amazing day!!! - This day was amazing!!!! There are some things you should know before hand. It doesn’t leave from Siena. It is a little town about 20 mins away. If you don’t have a car you need to spend the extra for pick up and drop off. I didn’t see that until the night before and we arranged a cab but that costs 30 euros each way so plan for that. Also the meeting place is very nondescript. It looks like you are being dropped off at an industrial building in the middle of no where. There is no signage. It is a big warehouse with gates that are closed and they will watch for you. We were all very lost at first. It needs better signage or directions. After you find it, it worth it! This day was amazing. You will ride the Vespas for 6+ hours all over Tuscany. It looks like a storybook and you stop in 4 different villages throughout the day along with the winery. The lunch and wine tasting is amazing. It is truly a tasting. You get 3 small pours. No one is getting drunk and totally able to drive back. We shared a Vespa which was fun and my husband thought he would drink more at the winery so I would drive back. I did drive back but it was very hard to balance a man on the back. Hard to start and stop. My husband mostly drove do to this so if you really want to drive get 2 Vespas. Also make sure you get your international driving permit. It took 10 mins at a AAA office in the US. I am giving you the specifics but what I want to say is that is was a day for the memory books!
Review provided by Viator
Suzi_m
May 26, 2025
Good tour but car issues - The tour itself was great. However, a Fiat 500 in our group was having mechanical issues, and we spent a large part of the tour waiting on the road for the car to be exchanged. This led to us missing all of our stops except the one at the vineyard. The vineyard was great, and the wine was good; however, lunch was unable to be provided. Overall, it was enjoyable, but it's disappointing to pay a large amount of money for a tour and only make 1/3 of the stops.
Review provided by Viator
Vikkib727
Jun 2, 2025
Avoid this tour. - I unfortunately can't recommend this tour. It started off with our reservation not being correct and costing more money to do the tour. I would also say that if you are not an expert motorcycle/vespa operator this tour is not for you as you are on busy streets with very impatient drivers. We were not able to complete the tour and honestly should not have passed the driving test that was given. We ended up in the emergency room with my son with 30 stiches. The tour guide was impatient from the start which created anxiety for the group. There are so many other tours that you can do this one you should avoid. If there is any damage they charge you are total was $3000 which is what we paid for our lodging.
Review provided by Tripadvisor
Marnik
May 25, 2025
A disaster. - The Vespa tour did not take place due to poor communication between Mytours.it and the practical operator of the tour. The practical executor was unaware of our arrival. I finally got someone from Mytours.it on the phone. I had to request a full refund via email to Mytours. This is what I did. Hopefully this will be sorted out soon. Our beautiful day fell in the water....
Review provided by Tripadvisor
Tim_r
May 17, 2025
False Advertising - Not told that have to pass a driving test. Should have experience due to roads and traffic. 1 hour late start cut time off stops. No lunch. No cost adjustment. Could add more negatives to list.
Review provided by Viator
Krystle_m
May 30, 2024
TERRIBLE and UNSAFE - Unfortunately this tour was very disappointing. It wasn’t a “tour” in the sense that someone shared highlights of the region with you — instead we were instructed to follow a pilot car and dropped in various villages with instructions to meet back at our vespas within 15-30 minutes depending on the spot. Seriously he spoke less than 10 words the entire day!? Also, there was NO instruction on how to get familiar or drive a Vespa, instead a quick “test” if you could drive it or no (many of us could not and FAILED the test and didn’t get a refund for the Vespa we never rode!!). He also took us on the freeway which was absolutely terrifying and felt very unsafe!!! Bottom line: NOT actually a tour. And certainly NOT for inexperienced Vespa/motorcycle/scooter riders.
Review provided by Viator
From $169
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).