Product image 0
Product image 0
Product image 1
Product image 2
Product image 3
Product image 4
1/6

Tuscany Road Bike Tour

7 days / 6 nights

|

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

Google ReviewsTripAdvisor Reviews

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
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 leisureful 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.

Val d’Orcia image 1

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 image 1

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.

Chianti image 1

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. 

Crete Senesi image 1

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 image 1

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 image 1

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

We offer road cycling, trekking cycling and mountain biking holidays.


Our road cycling holidays are suitable for avid road cycling enthusiasts whose endurance is high enough to withstand multiple long cycling days in a row.


Our trekking cycling holidays are suitable for anyone, as the stages are short enough for most people, and the terrain is not technical — mostly tarmac and gravel. They will still be enjoyed most by people who cycle occasionally and feel comfortable with multiple days in a row on the saddle and some moderate climbing. For those looking for more leisurely cycling holidays, we offer an e-bike option.


Our e-MTB holidays are suitable for most people comfortable on a mountain bike who are fine with some rougher gravel roads and steeper hills, made easier with electric assistance. However, the single trails MTB holidays are suitable mostly for avid mountain bikers, as they tackle technical trails and fast descents, but are very adjustable to your skills and style of riding.

On our guided tours, you will have professional local guides. Our guides will make sure that you will have expert guidance combined with great fun and a memorable experience.

We are always looking for the perfect fit for you. We use a few different accommodation providers that fit our standards but they are subjected to availability, especially in the high season. We can also adjust the holiday, keeping in mind your preferences and budget and can always find a more suitable solution for your taste.

We recommend booking as early as possible. Most of our tours run through very touristy places where accommodation is limited. Most of the great places start getting booked for summer before spring.

It really depends on the level of your restriction. Vegetarian options are fairly easy to find in Europe, but vegan dishes, on the other hand, are extremely hard to come by in rural areas and in smaller towns. Please note that the places where we stop for lunch are often traditional and may have difficulties accommodating you outside of their standard menu. We suggest you keep this in mind.

If you want to, sure! We are well aware that some people love to stay in groups while others prefer some more alone time on their trip. We wanted to give you the opportunity to do things your way. It is your holiday, after all! As long as you respect the group timings and locations designated by your guide, please feel free to customize your itinerary and create your own adventure!

Most of the tours can be done even in light rain, as long as you dress accordingly. It is not unusual in the summer that there are afternoon thunderstorms, so early starts are advisable. If the weather looks really bad, we will try to adjust the tour or skip a stage with a shuttle.

The best time for cycling in Europe varies depending on your preferences and the region you’re targeting. Spring offers moderate temperatures and scenic blooms in Southern Europe, while early summer is ideal for enjoying the mild climate and extended daylight in Northern Europe. Late summer to early fall in Central Europe is perfect for those who prefer cooler temperatures but still want to enjoy plenty of daylight. For winter escapes, consider warmer regions like the Canary Islands or Tenerife.

Ratings & Reviews

Google Reviews

5.0 average rating

John Woeste's profile photo
Alison Booth's profile photo
les chappell's profile photo
Abby Walker's profile photo
Ian Panting's profile photo
+84
Top Rated Brand
John Woeste's profile photo

John Woeste

Verified customer · 29 days 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.

Review 1
Review 2
Show all 3 photos
Alison Booth's profile photo

Alison Booth

Verified customer · 29 days 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.

Review 1
Review 2
Show all 3 photos
les chappell's profile photo

les chappell

Verified customer · about 1 month ago

Spent September cycling through Slovenia and Croatia on a self guided holiday, absolutely brilliant from accommodation to luggage transfers .

Review 1
Review 2
Show all 4 photos
Abby Walker's profile photo

Abby Walker

Verified customer · about 1 month ago

We loved the routes provided to us for the self-guided tour!! Hotels varied a bit in quality with the 3 and 4 star hotels but the breakfasts were all great!

Review 1
Review 2
Show all 4 photos
Ian Panting's profile photo

Ian Panting

Verified customer · about 2 months ago

Just back from enjoying a long weekend cycling in Slovenia, the company arranged transfers to and from the airport, hotels, bikes, bike routes, including what to see and where, and even transportation of bags between hotels. The only thing we needed to worry about was where to eat; the whole trip was painless, and I would highly recommend them.

Review 1
Review 2
Show all 3 photos
John Hahn's profile photo

John Hahn

Verified customer · about 2 months ago

Wow! What an awesome tour! We did a self-guided cycling tour on gravel bikes and it could not have been more enjoyable! Such a beautiful country and such an intimate travel experience. We biked through mountain valleys, over mountain passes, along rivers, through small villages, through wooded hills, through vineyards, and along the Adriatic coast. Kudos to everyone that put this trip together! The hotel accommodations were perfect and the bikes we rented were high quality! Thank you!

Review 1
Review 2
Show all 7 photos

Similar Products

All available guidance options

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

Hassle-Free

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

Trusted by many

Trusted by many

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Handpicked Adventures

Handpicked Adventures

Only the best hut to hut hikes in Europe, cherry-picked by our local team with an in-depth knowledge of the region.

Unbeatable support

Unbeatable support

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.

from 1.349 € /person
Experience Europe like never before with Cycling Holidays Europe. From scenic routes to cultural gems, discover the ultimate cycling vacations on two wheels.

Have questions? Talk to us.

Agent picture
Lan Lajovic
Usually replies within 1 hour!
Google ReviewsTripAdvisor Reviews
Portfolio brand of:World Discovery