Tuscany Road Bike Tour
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Tuscany Road Bike Tour

7 days / 6 nights

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Experience the breathtaking beauty, rich history, and exquisite flavors of Tuscany on a 7-day cycling tour, and explore the heart of this beautiful region.

Starting point

San Quirico d’Orcia

Finish point

San Gimignano

Fitness level

3/5

Season

From March to November

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Highlights

  • 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

What’s included in the price?

Self-guided

Tour design and organization
Booklet with detailed itinerary and route instructions
6 nights in a 3* hotels with breakfast
Service and support during your tour
GPS navigation with an easy-to-use app
Luggage transfer

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Airport transfer
E-road bike
Hotel upgrades
Road bike
Single supplement

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 leisurely experience. Explore the great Tuscany without breaking a sweat!

Top Places You’ll See

From natural wonders to authentic local culture, the route is packed with memorable sights—these are our absolute favorites.

Tuscan countryside in the Val d'Orcia during spring day, province of Siena, Italy

Val d’Orcia

A UNESCO World Heritage landscape, Val d’Orcia embodies the quintessential image of Tuscany — soft rolling hills, cypress-lined lanes, and medieval towns perched above golden fields. The valley, shaped by centuries of harmonious farming, has inspired painters since the Renaissance. Today, it remains one of Italy’s most photographed regions, where light, color, and human craftsmanship merge into a scene of perfect balance. 

Montalcino old town, Italy

Montalcino

Crowned by a medieval fortress and encircled by vineyards, Montalcino is synonymous with the celebrated Brunello wine. Its cobbled streets and honey-colored stone buildings tell stories of prosperity and pride. From the fortress ramparts, sweeping views extend across olive groves and the rolling Val d’Orcia.

Landscape panorama from Tuscany, in the Chianti region

Chianti

Between Florence and Siena, the Chianti region is a rolling tapestry of vineyards, cypress avenues, and hilltop villages. For centuries, its landscape has been shaped by winemakers whose craft is as refined as the land is beautiful. Medieval castles, rustic farmhouses, and the scent of grapes ripening in the sun create an atmosphere of harmony and abundance. 

typisch Toskana, Pinienallee vor einem Bauernhof, Crete Senesi, Toskana, Italien

Crete Senesi

South of Siena, the Crete Senesi unfold in a surreal landscape of clay hills, eroded gullies, and silver-gray soil. Often compared to a lunar terrain, this area changes color with the seasons — golden in summer, green in spring, and violet under stormy skies.

Siena

Siena

Siena’s medieval heart beats in the shell-shaped Piazza del Campo, where the famous Palio horse race takes place each summer. Once a rival to Florence, the city flourished in art, architecture, and civic life during the Middle Ages. Its striped cathedral, Gothic town hall, and frescoes by Lorenzetti reveal the depth of its cultural heritage. 

Our Bikes

To ensure the best possible experience on your cycling adventure, we offer top-quality bikes for rent. Our fleet features the latest models, meticulously maintained for both performance and comfort.

To match each rider with the right equipment, our team will also assist you in selecting the most suitable bike based on your physical profile, personal preferences, and the technical requirements of the tour.

Road Bikes

Best for: Paved routes, longer distances, and climbs


Our road bikes are lightweight, fast, and built for endurance. They typically feature carbon or high-quality aluminium frames, smooth gearing, and reliable components—often Shimano 105 or similar. Well-suited for long days in the saddle, they’re perfect for climbs, steady cruising, and covering serious distance on tarmac.


Frequently Asked Questions

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.

Our tours are categorized into three difficulty levels: leisurely, moderate, and challenging. Although each may include both easier and more demanding days, our rating system reflects the average difficulty level for a typical day.


Leisurely tours take place primarily on flat, paved cycling paths, asphalt roads, or easy gravel tracks, and they are suitable for all fitness levels.


Moderate tours may include some uphill climbs or technically more demanding terrain, but they are manageable for individuals of average fitness.


Challenging tours entail either long distances and numerous climbs or technical terrain, possibly featuring downhill sections requiring proficiency with a mountain bike.

Our tours can be adapted to any bike type, whether road, gravel, or mountain bike. We are in constant communication with you to find the optimal conditions for your cycling holidays in Italy.


The most versatile option is a gravel bike, even if you are coming on a road cycling holiday. It does not really affect your road performance while allowing you to take some scenic backroads that can be in a slightly worse state than the main ones. A gravel bike is usually more comfortable as well.

If you are not bringing your own bike and equipment, we can certainly arrange that for you. We have a wide selection of bikes at our disposal and we will choose the ones that best fit your tour. All we need from you is your usual bike size and any other relevant information or preferences so we can make sure you will be comfortable throughout your trip.

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.

Absolutely, the choice is yours! We understand that some travelers enjoy group activities while others prefer a more solitary experience. Therefore, we want to offer you the flexibility to personalize your trip to suit your preferences. After all, it is your holiday! As long as you adhere to the designated group timings and locations outlined by your guide, please feel free to customize your itinerary and embark on your own adventure.


If you want to have a completely independent holiday, you can always opt for a self-guided tour, which is possible on most of our tours!

The optimal time for our tours varies depending on the specific trip. However, typically late spring (May) and early autumn (September) are ideal. Of course, summer is also an excellent time to travel. Additionally, some of our holidays can be enjoyed in winter too!

With proper attire, most of our tours can still be enjoyed even in light rain. During the summer months, afternoon thunderstorms are not uncommon, so it’s recommended to start your day early. If inclement weather is forecasted, we will do our best to modify the tour or arrange for shuttle transportation to skip a particular stage.

Ratings & Reviews

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Gašper Kolenc

Verified customer · 9 months ago

Exploring Tuscany on a self-guided cycling holiday was pure joy. The carefully curated routes took me through vineyards, olive groves, and picturesque towns like Siena and Pienza. I loved being able to stop whenever I wanted to soak in the views or enjoy a cappuccino in a quaint café. The GPS and route notes were spot-on, and the logistics, from luggage transfers to charming accommodations, were seamless. Tuscany’s beauty is best experienced on two wheels, and the freedom to set my own pace made it unforgettable.

Mystie Pineda

Verified customer · 2 months ago

I found this place with a simple Google search, and I never could’ve expected the custom experience I received. They provided options to help my husband and I hone in on exactly what we wanted to do for our honeymoon. We had perfectly curated GPS-lead rides all across the country, they booked all of our hotels, and planned all of our transportation. Every place that we went was so beautiful. I’m so grateful that we found this company to help us plan our honeymoon, couldn’t have asked for a better experience!

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Bill Wright

Verified customer · 3 months ago

I was able to tailor a bike tour itinerary along the Adriatic coast that suited our group during the shoulder season. We added individual pre and post-trip activities which went smoothly. Our trip included stops in Italy, Slovenia and Croatia. The trip planner, guide and support team were great.

barney barnhart

Verified customer · 3 months ago

Brilliant planning, great communication, terrific hotels and accommodations, interesting cities and beautiful scenery plus amazing routes.

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John Woeste

Verified customer · 4 months ago

Highly recommend the bike trip from Bled to Pula. It was well planned. We did a small group self-supported. Big fun. Bikes, hotels, route selection and communication with the company was great.

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Alison Booth

Verified customer · 4 months ago

I would highly recommend anyone doing this tour take the e-bike option. There were only 3 of us on our tour who completed this on regular bikes. Four others who started out on regular bikes swapped over to e-bikes after the first day. The climbs are long and steep. There is pretty much only up or down, not much flat or undulating road. It is doable, but very challenging. If you are on an e-bike then this also helps with the group staying together and no-one having to wait too long for others to catch up. The bikes were really good and had great gearing that was capable of handling the steeper climbs. When we booked we were unaware that we would be riding in a group of 20plus at all time. Thankfully our group had prior group riding experience but we did observe other large groups with less than desirable riding behaviours.Others in our group were extremely understanding and supportive. Our guide, David, was very adamant about staying safe on the road. He was flexible with the itinerary and made changes to suit the weather conditions and to ensure we got in as much riding as possible. He was vey knowledgeable about Croatian history and agriculture and taught us lots about the country he is so passionate about. Our captain, Tolma, was also amazing and along with his awesome crew, made our cruise an enjoyable experience.

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Self-guided

Those who like good adventure and limitless flexibility should go on a self-guided cycling holiday. It offers complete freedom, multiple detour opportunities, and exploration at your own pace without having to adapt to a group.

Hassle-Free

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree holiday.

Completely Customizable

Flexibility is our middle name — whether you want more or less, or just beyond ordinary, we’ll make it happen.

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Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

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