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Tuscany Road Bike Tour

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
7 days / 6 nights
Tour type
From: 1,349€/person
Suitable for most active people with good stamina and basic cycling experience

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

Chianti panorama

Chianti panorama

Tuscany bike

Tuscany bike



Crete senesi

Crete senesi

Val d orcia

Val d orcia

Want to make some changes?

Tailor made holidays - let us know what works for you and we will make it happen.
Customize your holiday

Included in price

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

Luggage transfer

Optional Extras

Bike rental
Airport transfer
Extra days
Signle 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!


Average weather forecast

High (°F) 43 48 57 63 72 79 84 82 75 64 52 43
Low (°F) 30 32 39 45 54 59 64 64 57 48 39 32
Rain (in) 2 2 3 3 4 3 3 4 4 5 3 2
High (°C) 6 9 14 17 22 26 29 28 24 18 11 6
Low (°C) -1 0 4 7 12 15 18 18 14 9 4 0
Rain (mm) 59 49 65 75 95 67 66 89 93 122 76 61

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The sooner the better - guaranteed availability and best prices if you don't wait for too long.
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Things to know


Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday in Slovenia. 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.


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.

Book with confidence

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

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.

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Portfolio company of World Discovery.