Tuscany is deservedly world-renowned for having the many elements that make for an enriching travel experience. Traveling by bicycle allows us to enjoy the subtler aspects of this region, off of the ‘touristed’ main routes into the heart that is Italy.

Only Great Explorations:

  • Small groups, extraordinary guides, and authentic experiences
  • A ride you will never forget: Asciano to Pienza with a picnic along the way at a secret location where the view is breathtaking
  • A meal you will never forget: lunch at Tre Porte in the picture perfect village of Montichielo
  • Our guest chef will teach you how to make hand-made pici in an Italian kitchen
  • Order off the menu at restaurants you won’t find in guidebooks
  • Distinctive, charming hotels too small for larger groups
  • We design and operate our own trips so there are only good surprises



Siena, Province of Siena, Italy




Day 1+2



Day 3






Day 5+6

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guides and support vehicle
7 nights lodging
All breakfasts, 2 lunches, and all dinners but 1
Cooking course with guest chef
Entrance fees for selected historical sites and museums
Detailed map and route instructions
All baggage transportation
All transportation from initial meeting point to final drop-off (see arrive/depart cities)




Apr 11-18
Apr 18-25
April 27 -May 4*
May 13-20
Jun 15-22
Aug 22-29
Sept 2-9
Sept 12-19
Sept 26-Oct 3


Apr 10-17
Apr 17-24
April 26 -May 3*
May 13-19
Jun 14-19
Aug 21-28
Sep 2-8
Sep 11-18

*Consider this departure if you wish to do a two-week trip combining Tuscany and Umbria.

Custom and self-guided trips also available and can start any date.
Call or email for details.


8-16 participants


8 days / 7 nights


Siena / Chiusi


Moderate / Challenging
20-40+ miles daily
Van supported


1 day gently rolling, 3 days are moderately rolling, 2 days are hilly


Land Cost (current year):
US $3250
Includes 7B/2L/6D

Single Supplement:
US $740

Bike Rental:
US $180

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. Due to cancellations and waiting lists, trip availability fluctuates daily. If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at info@great-explorations.com or by telephone at 604.730.1247

Getting there :
Siena: Most participants will arrive via Rome or Florence the evening before our ‘trip rendezvous’.


Day 1+2

Castellina in Chianti

Meet in Siena and cycle north through fields and vineyards. After lunch in a tiny village, we’ll visit Radda on our way to Castellina. Exclusive wine tastings at a wine enoteca and dinner at a local trattoria. On our second day enjoy a scenic ride with a visit to the Castle of Meleto, which has marked the history of one of the most important families of the Chianti area. For those who would like a more challenging ride, San Gimignano’s medieval towers beckon from distant hills. The village, surrounded by stone walls boasts some of the best-preserved monuments in the region. If you are not up to riding back (up) to Castellina, our van will gladly provide a lift. Our hotel in Castellina, formerly a palace, is now one of the best in Chianti!
Distance D2: 46 km, elevation gain 690 m.*


Day 3


Our route takes us to Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate. Our hotel is located in the countryside with a pool and surrounded by an extensive park. For those interested in cooking lessons prior to dinner, the chef here will gladly demonstrate.
Distance: 54 km, elevation gain 699 m or 62 km, gain 868 m.*


Day 4


Our day starts with a gentle descent and then rolling hills west towards Monteroni d’Arbia for lunch. Along the way, you may have the chance to visit an eccentric artist who often invites us to his home – a castle filled with museum-class art. The day finishes with a ride (or shuttle) to the extrordinary Monastery Monteoliveto Maggiore, where a local guide describes frescoes here, painted by Signorelli and Sodoma in the 16th century.
Distance: 55 km, elevation gain 605 m or 78 km, gain 860 m.*


Day 5+6


We save the most spectacular riding for last as we visit the tiny villages of Petroio and Castelmuzio on our way to Pienza, full of Renaissance monuments. We’ll ride to Montepulciano and Monticchiello riding through a ‘photographers’s paradise’. Our hotel is quietly situated 150 meters from the central plaza and has large comfortable rooms and a casualness that you will enjoy. We’ll complement our final evening meal with bottles of the local wines and toast our time together in Tuscany. Viva la dolce vita!
Distance D5: 30 km, elevation gain 495 m or 46 km, gain 990 m.
Distance D6: 37 km, elevation gain 485 m or 81 km, gain 1136m.*


Day 7

Transfer to Chiusi for trains onward.

*Distance and elevation gains may vary depending on hotels chosen for specific departure.

Palazzo Squarcialupi, Castellina in Chianti

A former palace from the 15th century, this is one of our favourite hotels in Italy. Enjoy private salons, a terrace with views over the magnificent Chianti countryside, large swimming pool set in the garden, and a Turkish bath. Sip wines produced in the antique wine cellars beneath the hotel using grapes from the vineyards extending around the village.

Relais Borgo di Toiano, Sovicille

This 4-Star Tuscan villa boasts panoramic views over vineyards, with a pleasant swimming pool in a very quiet setting.

Hotel Borgo Casa Bianca, Asciano

This eighteen-century property is one of the most magnificent hotels in Tuscany. There is a large swimming pool, a hydro-massage bath tub, and tennis-courts, all surrounded by an amazing landscape.

Hotel Il Chiostro, Pienza

Formerly a convent, this hotel features views over the countryside from its gardens.


Trip Reviews

September 7, 2007

“Great group of people. Great Guides. Beautiful countryside. Great weather. Great food.”

May 10, 2014

“My rating of Tuscany as a region is off the charts; the landscape, the culture and history, the food and wine, and most of all the people, there is absolutely nothing not to like about Tuscany. My expectations of a tour of Tuscany were very high and this trip certainly did not disappoint. I’d encourage anyone wishing to savor the “dolce vita” to visit Tuscany and in order to experience what it is really like, to do it with Great Explorations.”

May 25, 2014

“The food, wine, landscape and our group dynamics made this trip very enjoyable. The Tuscany region is an stunning place to ride for the scenery and the quiet roads. Our guide Gabriele was awesome and made this trip that much more enjoyable.”

December 4, 2018

“Loved Tuscany. Some beautiful hotels. Great group of friends. Just some lovely memories.”

December 4, 2018

“Awesome guides!!! Harder and more fun than I expected! Totally stunning.”

January 25, 2019

We are a group of 16 very close friends who decided to go to Tuscany in September 2018. This was an unforgettable trip with incredible memories to last a lifetime. It was at times a huge challenge physically, and even mentally, but that’s part of what made it so memorable. I can’t say enough about the breathtaking scenery, the (best in the world) Italian food (my God the sunflower ravioli at the top of the mountain served by the nonna who was not expecting us!!), and the endless laughs and friendship that are so good for the soul. Thank you Robyn and Frederica for being wonderful caring guides. We’ll be back!

Leave a Review