Siena & Tuscany cycling tour

Discover Charming Sights in the Tuscany Countryside on a Relaxing Self-guided Cycling Holiday

Type: Self-guided cycling tour
Duration: 5 days
Availability: Daily
Special information: This is a self-guided cycling tour; however, guided tours are offered where indicated in the itinerary


Immerse yourself in the beauty of Tuscany on a relaxing bike tour

Tuscany is one of the most lush and picturesque regions of Italy and its rolling hills, vineyards and green landscapes, not to mention the fantastic Tuscan cuisine and pleasant climate, make it the perfect place to visit if you're looking for a biking holiday abroad.

Bellarome's Tuscany cycling tour takes you to some of the pretty towns that lie off the beaten track so you can experience the true Tuscany. Below, you will find an example itinerary but remember that we are happy to tailor any of the details to suit your needs - please call one of our dedicated team on (UK) 01223 637331 or (US) 1-347-594-5500 or Click here to send us an enquiry.

Example Itinerary

DAY 1 Arrival

  • Arrive at your 4 star accommodation in Asciano or Sinalunga

DAY 2 Crete Senesi (approx. 32 km)

  • Bike to Crete Senesi and Sinalunga Buonconvento, then through Trequanda Montisi to San Giovanni d'Asso
  • Take a bus to a Belvedere farm, where you can regenerate your energy with exquisite Tuscan sausages. Alternatively, you can lunch in Buonconvento at I Poggioli
  • Return to your hotel with free time for dinner

DAY 3 Val d'Orcia (approx. 35 km)

  • Depart from Sinalunga for Chianciano Terme, where you will pass by some of the most beautiful landscapes in the world
  • Arrive at Val d'Orcia and admire the spas and nature reserves
  • Pass through Montepulciano, Pienza, Bagno Vignoni and along Via Francigena and enjoy a stop at the local dairy for cheese tasting accompanied by wine from the local area
  • Visit Pienza and taste local balsamic vinegars and jams combined with pecorino cheese
  • Take a bus to Cortona for a short visit before returning to your accommodation for dinner

DAY  4 Chianti

  • Take a bus to the historic Chianti hillside, where the cycling tour begins
  • Ride through the League of Chianti, through the mountains from Radda in Chianti
  • Stop for lunch at a local restaurant and enjoy Ribollita accompanied by wine tasting
  • Continue after lunch to Castellina (free time to visit the area)
  • Dinner and overnight stay in Castellina

DAY 5 Departure

  • Breakfast at your hotel prior to departure

*Please note that the quoted prices are based on two people sharing a double room. The price includes 4 nights accommodation in a 4 star hotel and bike hire for 4 days, as well as a guide and bus transfers (where noted). Please note that flights and airport transfers are not included.