“Birthplace of the Renaissance, land of Dante’s poetry, and Chianti wine, Muse to Michelangelo”

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. Is this among the the most beautiful regions on earth? We think so. On our Classic trip, we stay in a combination of distinctive hotels, charming agriturismos and comfortable inns (except for Siena, all with fabulous swimming pools) and hosts that will welcome you with open arms. Enjoy!

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
  • 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
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

Not Included

Bike rental




Apr 7-14
Apr 14-21
May 8-15 (guaranteed)
Jun 11-20
Aug 18-25
Aug 23-30
Aug 30-Sep 6
Sep 8-15


Dates available upon request

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


4-16 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:
US $3,450
Includes 7B/2L/6D

Single Supplement:
US $860

Bike Rental:
US $325

E-Bike Rental:
US $560

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: We’ve decided to include your arrival night in Siena to make this an 8 day trip. If you wish additional nights in Siena at the trip hotel, simply let us know on your registration form. Most participants will arrive via Rome. Sienna is easily reached by train.


Day 1


Meet in Siena and start the tour with a walking tour with our favourite guide in the city. Enjoy a welcome reception and then we enjoy dinner at a local trattoria. Buon appetito!


Day 2+3

Castellina in Chianti

We cycle north through fields and vineyards. After lunch in a tiny village, we’ll visit Radda on our way to Castellina. Exclusive wine tastings before 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. Our hotel in Castellina, formerly a palace, is now one of the best in Chianti.
Distance D2: 46 km, elevation gain 900 m or 75km; 1335m Distance D3: 49km; 860m or 63km; 1050m*


Day 4


Start the day with a magnificent descent to the valley south of Castellina. Our route takes us to Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate. After an invigorating climb, enjoy lunch at a casual bistro in the countryside, followed by another lovely descent. Our hotel is located in the countryside with a pool and surrounded by vineyards. 
Distance D4: 56 km; 700m;  add-on option: 39km; 600m.*


Day 5


Our day starts with a gentle descent and then rolling hills west towards Monteroni d’Arbia for lunch and then to Casabianca where we stay at a an agriturismo owned by a mother and daughter whose shared passion is wine making. Along the way, ride (or shuttle) to the extraordinary monastery Monteoliveto Maggiore, where a local guide describes frescoes here, painted by Signorelli and Sodoma in the 16th century.
Distance D5: 55 km; 930m or 78km; 1370m.*


Day 6+7


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 D6: 30 km; 650 m or 46 km, gain 990 m.
Distance D7: 37 km; 735m m or 81 km, gain 1535m.*


Day 8

Transfer to Chiusi for trains onward.

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

Hotel Santa Caterina, Siena

This 18th century villa has been converted into a cozy hotel. Guest rooms overlook the valley. It is steps away from the medieval city gates with lots of restaurants to choose from a short stroll way.

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.

Casale Il Colombaio di Toiano, Sovicille

This property is from the 1300s and beautifully restored with lovely and congenial hosts, Giuseppina and Paolo. The rooms are comfortable and the gardens sublime.

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

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.”

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.”

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.”

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!”

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