• Location: Florence, Italy
  • Duration: 2 days (approx.)
From USD $ 534.74 View price calendar

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Pedal through the famous region of Chianti on this 2-day bike tour from Florence to Siena. Led by an expert guide, soak up the fresh air and scenic landscape as you cycle through one of the most famous wine regions in the world. Stop to savor a traditional Tuscan meal and olive oil tastings at wine estate, explore the medieval hill towns of Greve, Panzano and Radda and enjoy overnight stay at cozy, 3-star accommodations. When you finally arrive in Siena, opt to return to Florence by coach or extend your stay on your own.


  • 2-day bike tour through Tuscany to Siena from Florence with an expert guide
  • Cycle through the enchanting Chianti region past rolling hills and vineyards
  • See the pretty medieval hill towns of Greve, Panzano and Radda
  • Visit a private winery for olive oil tastings and enjoy two rustic Tuscan lunches
  • Stay overnight at a country villa, with dinner and breakfast included
  • Choose to return to Florence by minivan on arrival in Siena or stay on independently in the historic town
  • Small-group bike trip limited to a maximum of 15 for a more intimate atmosphere

Why Our Insiders Chose This Tour

What You Can Expect

2-Day Small-Group Tuscany Bike Tour to Siena from Florence

Cycle through Tuscany

Your 2-day bike trip departs from Florence and includes two lunches, dinner and hotel breakfast, as well as 3-star accommodations in a single or double room. When you arrive in Siena on the second day of your trip, your guide will provide transportation back to Florence, unless you choose to continue your stay independently. Additional tour details can be found in the Itinerary section below.


Customer Reviews


5 star rating: Highly Recommended September 2018

We had an awesome time on this two-day trip. Feddie was our tour guide and Cosimo assisted with the bags, equipment, and both were great. This was a really fun way to see Tuscany.

Jennifer M

5 star rating: Highly Recommended October 2017

This was a great tour! Our guide, Bill, was awesome. The whole experience was top notch. We biked through amazing country side with incredible views, ate at delicious restaurants for lunch, and had wine tastings. The villa we spent the night in was lovely, the food was great. Only wish it had been a bit warmer so we could've enjoyed the pool!
Highly recommend this tour and this company.

John Z

5 star rating: Highly Recommended July 2017

Bill Dillon from We Like Tuscany led the first and best bike tour of my life...something I dreamed to do 15 years ago when I first set my sights on the rolling fields of grape vines and olive trees. Bill was fun and knowledgeable, and my team mates on the tour were wonderful company. Highly recommended.

Cesar M

5 star rating: Highly Recommended June 2017

My wife and I recently took this 2 day bike tour. It was an amazing experience , it is the best way to see part if the Tuscany region. The views, the wine, the food and the biking was something we never experienced before . The first day you bike for about 19 miles then stop for lunch at a vineyard for your own private tour by your guide then taste the wines and food then you get on your bikes for another 20 or so miles before you arrive to a villa where you get to cool off in the pool before dinner . The next day you have breakfast and get back on your bikes for another 19 or so miles before stopping for lunch at a wonderful town in Chianti where you can taste the wonderful food and wine before getting on your bikes for another 20 miles or so and make your way to Siena . This trip was one of the highlight of our Italy trip , our guide Federico was fantastic, knowledgeable and conciencious. This is not an easy bike around the park trip , it is challenging and you need to be in decent shape . It is not for the faint-hearted, the roads are narrow with many curves and challenging uphill sand downhills . One of the best experience of our lives and will do it again. By the way although this is a small group tour my wife and I were the only ones on this tour. Before I forget , a Van takes your bags from Florence to Villa and from the Villa to Siena , you have an option to come back in the Van to Florence but we decided to stay in Siena. Best way to see Tuscany .

Oscar A USA

5 star rating: Highly Recommended October 2016

Bill and Terri were the best guides;the highlight of our trip to Italy. We received great personal care. We loved tasting the figs, grapes and observing the grape harvest; one of a kind experience. Bill was very patient and knowledgeable about the area. Suggest that cycling shorts recommend.

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