Explore the breathtaking landscapes of Tuscany
Visit charming medieval towns and villages such as Montepulciano, Monticchiello, and San Gimignano
Savor world-renowned Tuscan cuisine and wine through tasting tours and lunches at local wineries
Discover the rich history and culture of the region with visits to iconic landmarks
Upon your arrival in Toscana, take in the panoramic view of the Val d’Orcia region and the medieval village of San Quirico d’Orcia.
Relax and prepare for the thrilling journey that is ahead of you.
Hotel in San Quirico d’Orcia
Start your day with a delicious breakfast before setting out on a ride through the breathtaking landscapes of the Val d’Orcia region, a UNESCO World Heritage Site.
Stop at the “ideal” Renaissance city of Pienza, famous for its Pecorino cheese, and then continue on to Montepulciano with its winding streets and squares. Make a quick stop here before heading to Monticchiello, a small medieval and charming town.
Next, visit the medieval village of Bagno Vignoni, developed around its hot springs that were used by the Romans centuries before. Take a relaxing break from your cycling journey here before heading back to your hotel.
55km, 1150m elevation gain
As we climb towards Castiglione d’Orcia and Rocca d’Orcia, the stunning landscapes will make the challenging ascent worthwhile. Along the way, we’ll stop at the beautiful Abbey of Sant’Antimo, one of Italy’s most beautiful Romanesque churches, and enjoy a wine tour and tasting in a Brunello winery before climbing up to Montalcino. In Montalcino, a charming medieval town surrounded by vineyards, we’ll take in the beautiful valley views. We’ll return to San Quirico d’Orcia for a relaxing rest of the day and a final dinner in Val d’Orcia before heading to the Chianti region.
46km, 960m elevation gain
Experience a memorable journey through the stunning views of the Crete Senesi to the outskirts of Chianti. As we venture through the region, witness the unique badlands and landscapes that make the Crete Senesi area so distinct. Take a brief pause in Asciano, home to numerous churches and museums, before indulging in a delectable lunch and wine tour at a Chianti winery nestled in Castelnuovo Berardenga.
B&B in Castelnuovo Berardenga
55km, 770m elevation gain
Discover the picturesque towns of Castelnuovo Berardenga, Villa a Sesta, and San Gusmè, each with their own unique charm in the heart of Chianti. Marvel at the iconic Castle of Brolio, a symbol of the region’s history and renowned wines. Visit the birthplace of L’Eroica in 1997, the charming town of Gaiole.
Take a stroll through the quaint streets of Radda in Chianti, offering breathtaking views of the surrounding vineyards. Conclude your bike tour with a wine tour and tasting at a Chianti winery located near Radda in Chianti before returning to the hotel.
65km, 970m elevation gain
Embark on a journey through Siena, home to its magnificent medieval city center, the Duomo, and Piazza del Campo. Traverse the Montagnola Senese, where you’ll ride through lush woods and cross the Via Francigena pilgrimage route. Visit the renowned town of Monteriggioni, famous for its well-preserved old town and walls. Climb to the top of San Gimignano, also known as the “City of Beautiful Towers.” Enjoy a scrumptious lunch and wine tour at a winery along the route before returning to Villa Curina by van.
B&B in San Gimignano
62km, 800m elevation gain
After breakfast, you will check-out from your hotel and transfered to Siena or Chiusi-Chianciano train station for your journey back home.
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Tour design and organization
Booklet with detailed itinerary and route instructions
Service and support during your tour
GPS navigation with an easy-to-use app
Accommodation as per itinerary
Embark on an unforgettable cycling journey through the heart of Tuscany, where every turn of the wheel reveals breathtaking landscapes, rich cultural heritage, and exquisite culinary delights. This 7-day tour will take you on a magical adventure through the iconic Val d’Orcia region, where the rolling hills, winding roads, and medieval towns are a true feast for the senses.
From the “ideal” city of Renaissance time, Pienza, to the charming and picturesque towns of Montepulciano and Monticchiello, every stop along the way is an opportunity to immerse yourself in the history and beauty of Tuscany. Experience the warmth of the Italian culture through the local cuisine, such as the Pecorino cheese and Brunello wines, which are produced in this region and are renowned worldwide.
As you cycle through the scenic routes of the Crete Senesi and Chianti regions, you will discover a landscape of unparalleled beauty, with vineyards, olive groves, and ancient forests. Marvel at the impressive medieval castles and the well-preserved walls of Monteriggioni, and explore the charming narrow streets of San Gimignano, known as the “City of Beautiful Towers.”
The tour also includes visits to world-renowned wineries, where you can indulge in the tastes and aromas of the finest Italian wines. From the Abbey of Sant’Antimo to the Castle of Brolio, every landmark is a testament to the rich and fascinating history of Tuscany. The journey ends with a visit to the enchanting city of Siena, with its majestic medieval center and iconic landmarks, such as the Duomo and Piazza del Campo.
This tour is E-Bike friendly! This tour can be booked with e-bikes for a more leisureful experience. Explore the great Tuscany without breaking a sweat!
Our priority is to find the ideal accommodation that suits your needs. We collaborate with several lodging providers that meet our criteria, but please note that availability can be limited, particularly during peak seasons. Furthermore, we can tailor your holiday to align with your preferences and budget, and are committed to finding a more suitable alternative that matches your taste.
To ensure availability, we advise booking your tour as early as possible. Our tours typically pass through highly popular tourist destinations where lodging options are restricted. Many of these desirable locations become fully booked for the summer season well in advance, often filling up by spring.
The availability of food options in Italy depends on the extent of your dietary restrictions. While it is relatively easy to find vegetarian dishes, locating vegan meals can be challenging, particularly in smaller towns and rural areas. Additionally, the traditional lunch stops we make may have limited ability to accommodate special requests beyond their standard menu. We recommend considering this when planning your meals.
Our tours in Italy can accommodate various types of bikes, including road, gravel, and mountain bikes. We maintain constant communication with you to ensure the optimal conditions for your cycling holidays in Italy.
A versatile option for cycling in Italy is the gravel bike, even if you plan to embark on a road cycling holiday. It does not significantly affect road performance and allows you to explore scenic backroads that may be slightly rougher than the main routes. Furthermore, gravel bikes typically offer greater comfort and more control.
Italy is a diverse country with something for every cyclist. Regardless of your choice of bike, we will customize the perfect route for your cycling holiday.
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