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Cycle Tuscany: Florence, Chianti and Siena

We discover the varied and beautiful scenery of Tuscany with a rewarding ride between cultural highlights. From the renaissance capital Florence we ride through Chianti vineyards, olive groves and forests to the medieval hilltop town of Castellina in Chianti. We spend time in the ancient city of Siena before heading further south through classic, rolling Tuscan scenery to the charming hilltop villages of Pieve a Salti and Montepulciano.

Tour Highlights

  • Cycle Evocative Tuscan Landscapes - Through rolling forested landscape amongst vineyards and Cypress trees
  • Florence - Explore this renaissance city par excellence
  • Chianti Classico - Fine wine country
  • Siena - Free day in wonderfully atmospheric medieval city
  • La Toscana - Ride between medieval hilltop towns


Show more
  • 1
    Join tour in Florence

  • 2
    The Hills and Vineyards of Chianti

  • 3
    Cycle South to Siena

  • 4
    Free day in Siena; optional trip to Florence

  • 5
    Siena to Pieve a Salti via Le Crete

  • 6
    Classic Tuscany loop ride

  • 7
    Cycle to Montepulciano

  • 8
    Tour ends Florence Airport

Tour notes

Each departure date has it's own dedicated tour note, detailing all you need to know about that tour. Whether you've already booked, or weighing up your options, please choose carefully the relevant itinerary for you.

We have the following different versions of the Cycle Tuscany: Florence, Chianti and Siena tour available at present.

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Customer rating:
Cycle Tuscany: Florence, Chianti and Siena
5 out of 5 based on 4 ratings. Read reviews
Included meals 7 0 2
Breakfast Lunch Dinner
Bus, Bicycle
1 night Comfortable Hotel
6 nights Standard Hotel
Tour Staff
Driver(s), Explore Tour Leader / Cycle guide
Cycling Information
On this tour we cycle 282 km over five days (an average of 56 km per day). The terrain is hilly over the first two days and subsequent days are on the rolling Tuscan plain with ascents to hilltop towns. We cycle on tarmac roads (80%) and gravel paths (20%). A support vehicle accompanies the rides throughout the tour except on the circular route on day 6. We have graded the route as moderate.
Included Bike
27 gear Focus Black Hills mountain bikes with hybrid tyres and lockable front suspension
Group Size
Generally 10 - 16