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
Aug 27-Sep 3**
Sep 2-9
Sep 12-19
Sep 26-Oct 3


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

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

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


20-40+ miles daily
Van supported


1 day flat, 2 days gently rolling, 3 days are moderately rolling with some hills


Land Cost (current year):
US $2850
Includes 7B/2L/5D

Single Supplement:
US $630

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 is a charming 3-star hotel, close to cafes and restaurants.
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: 57 km, elevation gain 530 m or 110 km, gain 1240 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 dolce!
Distance D5: 46 km, elevation gain 350 m or 66 km, gain 555 m.
Distance D6: 41 km, elevation gain 741 m.*


Day 7

Transfer to Chiusi for trains onward.

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

Il Colombaio, Catellina-In-Chianti

This charming hotel has comfortable rooms, and a lovely swimming pool. Located close enough to walk to restaurants in Castellina-in-Chianti.

Le Valline, Sovicille

Located among the hills of the Crete Senesi and the Val di Merse, this hotel boasts outstanding views in every direction, a large swimming pool and a tranquil setting.

Podere Alberese, Asciano

This property is our newest discovery; this family-owned 17th century property is surrounded by vineyards (the family makes outstanding wines), olive trees and organic gardens. There is a heated swimming pool to enjoy on the property.

Hotel San Gregorio, Pienza

This 3-star hotel is conveniently located steps to the historical district of Pienzain in the heart of Tuscany. All rooms are finely furnished suites complete with sitting rooms and Jacuzzi tubs. A new swimming pool and restaurant were added in 2007 making this an extremely comfortable hotel.


Trip Reviews

October 10, 2012

“The trip exceeded my expectations on all levels. The location, hotels, food, extra activities – all of this made for an amazing package and a great value. The guides were exceptional – extremely knowledgeable about the area, thoughtful, helpful and so much fun to be with!”

August 30, 2016

“We loved the scenery, the old hill towns, the food, the wine: the whole experience was fantastic. Our guide was great! He was so knowledgeable about the areas we traveled in, made excellent choices for activities and restaurants, and was very supportive.”

January 5, 2018

“We found the people we met made the trip so special. Several of us have already been talking about which trip to go on next year.”

December 4, 2018

“Surpassed my expectations. My family had a fabulous time. I especially like how flexible and resourceful the guides were – like finding extra biking gear when ours was lost, checking in and out of hotels, adapting the biking and daily plan based on our requests. They were also very professional and engaging in conversation. We learned much about the region from them. They helped make the trip one we will all remember. We like all of the hotels – each one had a unique flavor and view.”

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