2 days

Chianti and Val D’Orcia Motorbike Tour. This 2 days motorcycle adventure tour in Italy will allow you to discover some of the best towns of Tuscany and enjoy the wonderful landscapes of the Chianti and the Val D’Orcia (the South of Siena). During these two days we will ride our motorbikes over more than 350 kms (no highways) for a total of near 8 hours ride. We will visit many towns such as: Monteriggioni, Siena, Montalcino, Pienza, Castelnuovo Berardenga, Radda in Chianti and Greve in Chianti. We will also visit a famous Abbey and spend a night in the heart of the beautiful Val D’Orcia. A great experience which we consider a MUST of you wish to see the landscapes and towns that have made Tuscany world famous.

DEPARTURE TIME Please arrive at least 30 minutes before the departure.
DISTANCE 350 km / 217 miles
Hotel with breakfast Motorcycle Rental
Guide on bike Internet Wi-Fi
Food and beverage

For this tour you can choose 4 different motorcycle options:

Type A: Ducati Multistrada V4, BMW R1250GS, HD Street Glide Special (or similar)
Type B: Ducati Multistrada 950, BMW F850GS, Moto Guzzi V85 TT, HD Road King (or similar)
Type C: Ducati Scrambler 800, BMW F750GS, Moto Guzzi V7, HD SuperLow (or similar)
Your own bike (more than 250 cc)

Please note that if your preferred motorcycle is not available for your dates, you can choose an available alternative from the same Type. If you change Type we will change the price accordingly. Please, visit our Rental Service page to see the accessories you can rent from us.


Your own bike Rental Type A Rental Type B Rental Type C
Single rider 590 €* 990 €* 950 €* 890 €*
Rider + passenger 970 € 1.370 € 1.330 € 1.270 €

*extra for single room: 70 euros per night


Wish to ride alone with your riding buddies? Private Motorcycle Tours in Italy are a great way to enjoy the adventure. Contact us with your preferred dates and group details. We will check the availability for your tour dates and will come back to you with a price quote for your special request. Please note that even if the minimum number of participants won’t be reached by your group, you might still be able to do the tour but with different prices than the standard.


  • 1 night in hotel (2 people per room)
  • Breakfast
  • Internet Wi-Fi
  • Motorcycle rental with unlimited mileage and insurance (not if you use your own bike)
  • English speaking guide on his motorcycle


  • Fuel
  • Food and beverage
  • Rental gear
  • City taxes, tips…
  • All services not mentioned as included and all items of a personal nature
  • Single room for an extra price of 70 euros per night


A payment of 30% is requested upon confirmation
The remaining 70% is due 30 days before the tour
For more information, please visit our FAQ’s



Check this video with the route of this tour!


We’re on Spanish National TV!


Day 1 - 9:30 Departure

Meeting at 9:00 in Florence and departure at 9:30. We will ride through the Cassia road to the heart of the Chianti: Castellina in Chianti for a coffee.


From Castellina we will go south to the medieval town of Monteriggioni.

Siena and lunch

After a quick visit to Monteriggioni, we will continue our journey to Siena where we will have time to make a walk and have lunch.


Time to visit this wonderful town famous for it’s wine.

Abbey of Sant'Antimo

Only a few more kms to reach the Abbey of Sant’Antimo, a former Benedictine monastery almost 1.000 years old!

18:00 Arrival to the hotel and relax

We will spend the night and have dinner in a nice quiet place in the countryside.

Day 2 - 9:30 Departure

Meeting after breakfast towards Pienza.


We will enjoy this little medieval city, it’s narrow streets and the fantastic view over the country.

Lunch at Castelnuovo Berardenga

We will start to go North and will stop for lunch.

Radda in Chianti

Keep riding across the Chiantishire to Radda for a walk, coffee or gelato.

Greve in Chianti

Our last stop on this tour: we will see the main town of the Chianti: Greve in Chianti.

18:00 Return to Florence

We will get back to the start point from the Chiantigiana road and give back the motorcycles.

Tour Reviews

5.00 based on 4 reviews
August 12, 2017

My experience with Tuscany Motorcycle Tours was excellent from start to finish. Before I made a reservation they answered all of my questions quickly, and were super helpful. The service here is way beyond what I expected, I really hope that I can return one day I join them on another tour. If you are considering renting a motorcycle or taking a tour of Tuscany, I can’t recommend this place enough.

Thanks again Gareth and Sarah!

September 10, 2018

Every year, my wife and I, make a motorcycle trip usually in Europe. This year we decided to visit the North of Italy but do to bad weather in the Alps, we decided to move South towards Tuscany and contacted Tuscany Motorcycle Tours to get a quick, smart and easy proposal. They offered us this Chianti and Vald Orcia tour that was just PERFECT for our needs. Not too long, not too short, beautiful towns, amazing landscapes, great staff, affordable and reasonable prices… We are just so happy to have found them! Will come back another year to try the one week tour of Tuscany!

June 14, 2019

Adrian is a great guide. He communicated with us via email to arrange all the details before we arrived. Everything went smoothly from when we met to pick up our bike. The roads we rode were great , the scenery beautiful, the towns magical & Adrian shared information and history on each. Our accommodation was excellent and the food fantastic. We would definitely recommend Adrian & Tuscany Motorcycle Tours

June 14, 2019

Thank you Julianne!!!

May 7, 2022

May 2022 • Friends
My boyfriend and I along with a friend took the two day Tuscan tour with Adrian. It was amazing! The roads were made for motorcycles with swooping curves and smooth surfaces. Everywhere you look is something beautiful. Adrian was our tour guide and he was so knowledgeable about the region and each stop along the way. He took the time to take a lot of photos of our group and emailed them to us at the end of the tour. The ride, the scenery, the food and wine…simply divine! I know Ron and I will be back for another tour. This was Ron’s (my boyfriend) second tour with Adrian and Tuscany motorcycle tours.

May 9, 2022

Thanks Liz, I hope to see you guys soon for another adventure!

Leave a Review