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

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  • 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 3/4* 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!

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

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Greg Martin

Verified customer · 11 months ago

Great holiday. Really easy to follow routes, good choice of hotels and the en route places to eat and visit was really helpful. Super responsive to questions during my holiday. Would definitely use them again.

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Andrija V.

Verified customer · 4 months ago

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Mitch Taylor

Verified customer · 9 months ago

Mitch Taylor's profile photo

Mitch Taylor

Verified customer · 9 months ago

SHONA Goaman's profile photo

SHONA Goaman

Verified customer · 10 months ago

Well organised, great route and lovely hotels.

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Sp/f Martin Mørk

Verified customer · 10 months ago

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Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday. We prepare the itinerary and book your accommodations; You enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.

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.

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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.

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Lan Lajovic
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