“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 Ristorante Daria in the picture perfect village of Monticchiello
  • Our guest chef will teach you how to make pizzas in an outdoor 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
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 5-12
Apr 12-19
April 21-28
May 8-15
May 23-30
Jun 9-18
Aug 16-23
Aug 21-28
Aug 28-Sep 4
Sep 4-11
Sep 12-19
Sep 25-Oct 2


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


Moderate / Challenging
20-40+ miles daily
Van supported


There are invigorating and rewarding hills every day of this tour


Land Cost:
US $3,950
Includes 7B/2L/6D

Single Supplement:
US $990

Bike Rental:
US $325

E-bike Rental (on request):
US $560

E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.  

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. Not only does she know all about the history and monuments, she invites us to her family’s villa overlooking the city for our welcome reception. We follow this with dinner at a restaurant that can only be described as favoloso. Welcome to Tuscany, having fun yet?


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 luxurious and charming property. 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 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.

Palazzo Squarcialupi, Castellina in Chianti

This palazzo boasts a superb location, right in the historic center of Castellina, with spacious lounges and bar, and a large outdoor swimming pool. Friendly and professional management.

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. Breakfast is served on the terrace overlooking the rolling valley.

Hotel Borgo Casa Bianca, Asciano

This 18th century property is one of the most magnificent 4-star hotels in Tuscany. There is a large swimming pool, a hydro-massage bath tub, and tennis-courts, all surrounded by amazing landscapes. There is a great restaurant on site.

Hotel Il Chiostro, Pienza

Formerly a Franciscan convent, this 4-star charming hotel boasts comfortable rooms, outdoor swimming pool and a fine restaurant with terrace overlooking the stunning Val d’Orcia valley.


Trip Reviews

October 26, 2023

“We like the smaller groups, the great destinations, great accommodations and the activities (cooking class was amazing!). Our guide was amazing – very enthusiastic, very helpful, very knowledgeable and very skilled! We would LOVE to have her as a guide on future trips!”

October 28, 2022

“I asked a lot of questions prior to the trip and all were answered thoroughly and with patience. Our guide, the caliber of the hotels, the itinerary in terms of village and bike routes, the quality of the bike, the cooking class and the guided walking tour of Sienna all exceeded my expectations.”

June 5, 2022

“Trip was excellent overall. This was my wife’s first bike trip and she was blown away. You have a new convert! RideWithGPS was great.”

October 22, 2019

“Our expectations were very high and they were met. Region was lovely. All hotels were great. Loved the picnic by the side of the road. We really enjoyed the people we toured with including Robbin, Dimitri and Adrien. Happy you guys decided to do electric bikes. Made it enjoyable (possible!) for some members of our group. We’re GE frequent flyers.”

October 15, 2019

“Surpassed expectations. Pure fun. Great people in an amazing setting. Beautiful albeit challenging routes. Plentiful extracurricular fun! Superb guide availability. Last meal in Pienza was fab and a nice change up. I wouldn’t change anything- loved it.”

October 9, 2019

“Loved the scenery, company (friends also repeaters) and food. Meals were amazing, rides were challenging, love that e bikes allowed some of our less fit friends to join us! Our group (moderate riders) was paired with a group of more elite riders, this was intimidating to some. We all had a great time regardless. I prefer to be a follower, guides were great to keep us corralled. Dimitri and Adrien and Robbin were awesome!! The region is stunning!! This is trip #5 with Great Explorations.”

October 9, 2019

“Excellent! Enjoyed staff and guests the most.”

June 12, 2019

“We wanted to send a heartfelt thank you for our phenomenal Tuscany cycling trip, it was beyond our expectations. Our guides (Mateo and Jacopo) were incredible, insightful, knowledgeable and just a whole lot of fun. We cannot say enough about them. Even when the “tsunami hit” and we could not cycle one day, they planned a wonderful schedule of exploring and wine tasting. We will, without a doubt be booking with your company again, and hopefully can request our two favorite guides!”

January 25, 2019

“We are a group of 16 very close friends who decided to go to Tuscany. 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 to our wonderful caring guides. We’ll be back!”

December 4, 2018

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

December 4, 2018

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

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.”

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.”

September 7, 2007

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

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