Heart of Tuscany

Dive into a Renaissance Landscape on this Quintessential Tuscany bicycle tour

Download a Detailed Itinerary

Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:

  • A thorough daily itinerary
  • Details for exact accommodations
  • What to expect
  • Travel planning tips

Please provide your contact information so that we can say “benvenuto”. After submitting the form, you will be able to download the itinerary immediately.

Biking on the Heart of Tuscany tour
Street festival in Tuscany

Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.

  • Van support
  • Service of local, professional guides throughout the program
  • Ciclismo jersey and water bottle
  • Cooking class by local chef
  • Olive oil tasting
  • 2 wine tastings
  • Guided walking tour of Siena
  • Cycling clinics
  • Shuttle at the beginning and end of the tour



What’s Included

  • Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
  • Garmin Edge Explore GPS loaded with the GPX tracks of your rides
  • Two water bottles
  • Saddle bag with repair kit
  • Optional: Map holder on handlebar

Pedal Options

  • Flat pedals
  • Half-toe pedals (without straps)

What’s Not Included

  • Helmet
  • Optional: clipless/SPD pedals with shoes
  • Optional: your own saddle
  • All accommodations
  • All breakfasts
  • 3 lunches + 1 picnic
  • 5 dinners

Chianti is a wine practically synonymous with Italy, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you quickly appreciate on our Tuscany cycling adventures. We pedal first to Montalcino, the hometown of the most famous Tuscan red, the Brunello di Montalcino. We also track through Greve and Panzano, immersing ourselves in Chianti along the way!

Complemented by outstanding meals, you also learn from the experts about the finer points of Tuscan cuisine and its excellent olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides), you take part in cooking class in authentic Tuscan cuisine. We also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.



May 27-Jun 2
Jun 28-Jul 5
2 spots available -- please call! SPECIAL EDITION: Tour de France and Palio di Siena (8 days)
Sep 7-13
Oct 7-13
Call for availability!


May 20-26
Jun 29-Jul 4
Palio di Siena Festival!
Aug 31-Sep 6
Oct 12-18
From $5,250 PP 7 days / 6 nights
From $5,300 PP 7 days / 6 nights
$1,225 Optional Single Supplement
Any of our tours can be made private. Contact us to learn more.

Confirmed tours are dates that have been selected by us that have a very high probability of reaching the minimum group size for us to run the tour and for you to receive the best Ciclismo Classico experience. These tours are confirmed as much as a year in advance, compared to our regularly scheduled tours which are confirmed around 90 days prior to departure.  When you place your deposit for a confirmed tour, you have the green light to make your pre and post travel plans and even book your flight with our personal guarantee that your tour will run!

Optional Single Supplement

If you are traveling alone, this optional single supplement will guarantee you a room to yourself at each hotel. The cost of a single room is often more than half the price of a shared room, so this additional supplement reflects that increased cost for each night over the course of the trip.