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.
“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 from Asciano to Pienza with a picnic along the way at a secret location with a breathtaking view
- 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
Tuscany Biking
Siena
Siena, Province of Siena, Italy
Arrival
Castellina-in-Chianti
Castellina-in-Chianti
Day 1+2
Sovicille
Sovicille
Day 3
Asciano
Asciano
DAYS 4
Pienza
Pienza
Day 5+6
Trip Inclusions
What’s Included
- 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
- GPS routes and maps
- All baggage transportation
What's Not Included
- Bike rental
Particulars
Departure Dates
| 2026 | 2027 |
|---|---|
| Apr 19-26 | Apr 18-25 |
| May 3-10 | May 2-9 |
| May 17-24 | May 16-23 |
| Jun 7-14 | Jun 6-13 |
| Jun 21-28 | Jun 20-27 |
| Sep 6-13 | Sep 5-12 |
| Sep 13-20 (PRIVATE) | Sep 19-26 |
| Sep 20-27 | Oct 3-10 |
| Sep 28-Oct 5 | |
| Oct 4-11 |
Trip can start at any date. Custom and self-guided trips also available. Call or email for details.
Trip Size
4-16 participants
Total Days
8 days / 7 nights
Arrive/Depart
Siena / Chiusi
Activity Level
Moderate / Challenging
20-40+ miles daily
Van supported
Terrain
There are invigorating and rewarding hills every day of this tour
Cost
Land Cost:
US $4,300
Includes 7B/2L/6D
Single Supplement:
US $1090
Bike Rental:
Hybrid Bike: US $380
Racing Bike: US $480
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.
Additional information
| Level | Avid, Moderate |
|---|
Getting There
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.
1
Day 1
Sienna
Meet in Sienna 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 often 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?
2
Days 2
Castellina in Chianti
Today’s ride takes us north from Siena into the heart of Tuscany, where quiet country roads wind through rolling hills, sun-drenched vineyards, ancient olive groves, and fields dotted with cypress trees. Along the way, you’ll experience the timeless beauty of the Chianti countryside, with breathtaking views around every bend.
We’ll stop for a leisurely lunch in the charming hamlet of San Sano, a peaceful village that perfectly captures the relaxed pace of rural Tuscany. Afterward, we continue through the renowned Chianti Classico wine region, visiting the medieval hill town of Radda in Chianti, where narrow stone streets, artisan shops, and panoramic vistas invite exploration.
Our day concludes in the picturesque town of Castellina in Chianti, one of Tuscany’s most celebrated wine destinations. Before dinner, enjoy an exclusive wine tasting at a local winery, sampling exceptional Chianti wines while learning about the region’s centuries-old winemaking traditions. We then gather for a memorable dinner at a traditional local trattoria, savoring authentic Tuscan cuisine paired with the outstanding wines of the region—a fitting finale to a day immersed in the landscapes, flavors, and culture of Chianti.
Distance: 46 km, elevation gain 900 m or 75km; 1335m Distance
3
Day 3
Castellina in Chianti
Departing from Castellina, today’s ride winds through some of the most picturesque landscapes of the Chianti Classico region, where vineyards, oak forests, and quiet country lanes reveal the timeless beauty of rural Tuscany.
A highlight of the day is a visit to the magnificent Castle of Meleto, one of Chianti’s most iconic historic estates. Originally established in the 11th century, the castle became the residence of the powerful Ricasoli family, one of Tuscany’s oldest noble dynasties. During the long-standing conflicts between the Republics of Florence and Siena, Meleto occupied a strategic frontier position and was fortified to defend the Florentine territories. Over the centuries, the castle evolved from a medieval fortress into an elegant country estate, and today its beautifully preserved towers, Renaissance courtyards, and surrounding vineyards offer a fascinating glimpse into the region’s rich history and winemaking heritage.
Continuing through the rolling hills of Chianti, we return to Castellina in Chianti, where you’ll spend the evening at our exceptional hotel. Once an elegant noble palace, it has been thoughtfully restored into one of the region’s finest boutique hotels, combining historic character with modern comfort. Relax before enjoying another memorable evening surrounded by the beauty, history, and celebrated wines of Tuscany. Distance: 49km; 860m or 63km; 1050m*
4
Day 4
Sovicille
Begin the day with a spectacular descent from Castellina, enjoying sweeping views over the rolling Chianti countryside as quiet roads lead into the valley below. Today’s ride showcases a wonderful mix of vineyard-lined lanes, ancient olive groves, and picturesque hilltop vistas that define this remarkable corner of Tuscany.
Our destination is the beautifully preserved medieval village of Monteriggioni, one of Italy’s finest walled towns. Built by the Republic of Siena in the early 13th century as a defensive fortress against rival Florence, its imposing stone walls and fourteen watchtowers remain remarkably intact, creating an unforgettable first impression. Within the walls, narrow cobbled streets, charming piazzas, and centuries-old buildings transport visitors back to the Middle Ages. The fortress was so renowned that Dante Alighieri referenced its towers in the Divine Comedy, a testament to its importance and striking appearance.
After exploring Monteriggioni, the route climbs through the countryside before rewarding your efforts with a leisurely lunch at a welcoming country bistro, where seasonal Tuscan cuisine and local wines provide the perfect midday break. A gentle descent follows, leading through peaceful vineyards and cypress-lined roads to our countryside retreat.
Tonight’s hotel is a tranquil estate nestled among vineyards and olive groves, offering elegant accommodations, a relaxing pool, and spectacular views of the surrounding Tuscan landscape—the perfect setting to unwind after another memorable day in the saddle. Distance: 56 km; 700m; add-on option: 39km; 600m.*
5
Day 5
Asciano
Today’s ride begins with a gentle descent before meandering through the rolling hills of the Tuscan countryside toward Monteroni d’Arbia, where we’ll pause for a relaxed lunch. Quiet backroads, wheat fields, vineyards, and olive groves provide a beautiful backdrop as we continue toward Casabianca, home to our elegant countryside retreat.
Later in the afternoon, you’ll have the option to cycle or take a shuttle to the magnificent Abbey of Monte Oliveto Maggiore, one of Tuscany’s most important Benedictine monasteries. Set amid the dramatic clay hills of the Crete Senesi, the abbey is renowned for its spectacular Renaissance frescoes by Luca Signorelli and Il Sodoma, depicting the life of St. Benedict. Distance: 55 km; 930m or 78km; 1370m.*
6
Day 6
Pienza
We save some of Tuscany’s most spectacular riding for our final day, following quiet roads through the breathtaking Val d’Orcia, a UNESCO World Heritage landscape renowned for its rolling hills, cypress-lined lanes, and postcard-perfect scenery. Along the way, we pass through the enchanting villages of Petroio and Castelmuzio before arriving in Pienza, the Renaissance masterpiece commissioned by Pope Pius II in the 15th century as his vision of the “ideal city.” With its harmonious architecture, elegant piazzas, and sweeping views across the Orcia Valley, Pienza is one of Tuscany’s true cultural and architectural treasures. Distance: 30 km; 650 m or 46 km, gain 990 m.
7
Day 7
Pienza
From Pienza, we continue through what many consider a photographer’s paradise, where vineyard-covered hills, ancient stone farmhouses, and winding cypress-lined roads lead us to the Renaissance hill town of Montepulciano, famed for its elegant architecture and celebrated Vino Nobile. We also visit the beautifully preserved village of Monticchiello, a timeless medieval hamlet perched above the Val d’Orcia, where every turn offers another unforgettable Tuscan vista.
Our journey concludes with a memorable farewell dinner, accompanied by bottles of the region’s exceptional wines as we celebrate a week of remarkable cycling, unforgettable scenery, new friendships, and the simple pleasures of Tuscan life.
Viva la dolce vita!
Distance: 37 km; 735m m or 81 km, gain 1535m.*
8
Day 8
Depart
Transfer to Chiusi for trains onward.
*Distance and elevation gains may vary depending on hotels chosen for specific departure.
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. *note- Il Chiostro is currently closed with an uncertain re-opening date. Unless and until it re-opens we will be booking alternate accommodation in or near Pienza.
Tour Reviews
“Great group of people. Great Guides. Beautiful countryside. Great weather. Great food.”
“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.”
“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.”
“Loved Tuscany. Some beautiful hotels. Great group of friends. Just some lovely memories.”
“Awesome guides!!! Harder and more fun than I expected! Totally stunning.”
“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!”
“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!”
“Excellent! Enjoyed staff and guests the most.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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!”
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