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
Sep 4-10
Sep 14-20

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

Apr 12-18
Apr 19-25
April 28-May 4
May 13-19
Jun 16-22
Aug 23-29
Sep 3-9
Sep 13-19

Trip Size:

8-16 participants

Total Days:

7 days / 6 nights


Siena / Chiusi


Palazzo Squarcialupi, Castellina in Chianti

Relais Borgo di Toiano, Sovicille

Hotel Borgo Casa Bianca, Asciano

Hotel Il Chiostro, Pienza

Activity Level:

20-40+ miles daily
Van supported


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


Land Cost (current year):
US $2950
Includes 6B/2L/5D

Single Supplement:
US $740

Bike Rental:
US $180

Tuscany, Biking Luxe

"...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 or Florence the evening before our ‘trip rendezvous’.

DAYS 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:
Sovicille - 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:
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: 55 km, elevation gain 605 m or 78 km, gain 860 m.*

DAYS 5+6:
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 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.

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

Map of the Area

Ride Info

Siena Weather

What is included in the cost of your trip?

  • Services of one or more experienced Great Explorations guides and support vehicle
  • 6 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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