Great Explorations

(800) 242-1825
(604) 730-1247

National Geographic



“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.”

– Kay & Jim D,
Burlington, VT

More testimonials


Trip Dates:

Apr 13-19
Apr 20-26
April 29 -May 5*
May 14-20
Jun 17-23
Aug 24-30

Aug 29-Sep 4**
Sep 4-10
Sep 14-20

Apr 12-18
Apr 19-25
April 28-May 4*
May 13-19
Jun 16-22
Aug 23-29

Aug 28-Sep 3**
Sep 3-9
Sep 13-19

*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.

Trip Size:

8-16 participants

Total Days:

8 days/ 7 nights


Siena / Chiusi


Palazzo di Valli, Siena


Il Colombaio, Castellina in Chianti

Relais Borgo di Toiano, Sovicille

Podere Alberese, Asciano

Hotel San Gregorio, Pienza

Activity Level:

20-40+ miles daily
Van supported


moderately hilly


Land Cost (current year):
US $2850
Includes 6B/2L/5D

Single Supplement:
US $630

Bike Rental:
US $180

Tuscany, Biking

"...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.

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.


Getting there :
Siena: Most participants will arrive via Rome. Sienna is easily reached by train.

Siena - We meet in Siena at 4pm at the first hotel and enjoy a walking tour of the historic center, followed by a welcome reception and dinner at our favourite restaurant.

DAYS 2+3:
Castellina in Chianti - Cycle north through fields and vineyards. After lunch in a tiny village, we’ll visit Radda on our way to Castellina. We enjoy 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 4:
Toiano - Our day begins with a long descent to the valley to Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate. After lingering here, climb up through a pine forest to a country restaurant that makes an ideal lunch venue. Our hotel is located just outside a small village with a pool and surrounded by vineyards.
Distance: 54 km, elevation gain 699 m or 62 km, gain 868 m.*

DAY 5:
Asciano - 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.*

DAYS 6+7:
Pienza - 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 8 : Transfer to Chiusi for trains onward.

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


  • What's Included
  • Weather
  • Ride Info
  • Map

Map of the Area

Siena Weather

Ride Info

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
  • Entrance fees for selected historical sites and museums
  • Cooking course with guest chef
  • Detailed map and route instructions
  • All baggage transportation
  • All transportation from initial meeting point to final drop-off (see arrive/depart cities)

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 or by telephone at 604.730.1247



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