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Tuscany Countryside Bike Tour

Bike through the "Green Heart" of Italy in Umbria and Tuscany

Tour Duration

5D / 4N

Trip Style

Discover, Classic Guided

Activity Level


Hotel Level



Trek Domane SL 7
Trek Electric-Assist Verve+
Trek Electric-Assist Domane+ SLR 7

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Starting from

$2,299.00 per person

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Discover two of Italy's premier cycling destinations: lush Umbria, renowned for its exquisite olive oil, and the noble Montepulciano wine region.

This captivating bike tour traverses two of Italy's most scenic regions, Umbria and Tuscany. Let us take you along serene country roads to discover their enchanting medieval towns. Begin your adventure in Umbria, Italy's "Green Heart," pedaling through rolling hills, vineyards, and olive groves. Immerse yourself in the charm of Umbria's hilltop towns like Bevagna, Montefalco, and Assisi, each showcasing the region's vibrant culture and artistic heritage. As you journey to southern Tuscany, witness the transformation into a picturesque landscape of bountiful fields and elegant farmhouses framed by cypress trees. Starting from Montepulciano, a renowned wine region, explore captivating hilltop towns and uncover the ancient tradition of winemaking. Let the sun-drenched scenery be your backdrop as you discover Tuscany's incredible cycling, delectable cuisine, and world-class wines.
Also see our Tuscany Bike Tour » and our Tuscany Wine Country Bike Tour »

Trip Wows
  • Soak up the medieval ambience and ancient traditions in the quintessential hilltop towns of Pienza and Cortona

  • Indulge in the olive oil and wine tastings in Tuscany and Umbria, where the best quality is produced

  • Bike through timeless towns and enchanting farms nestled in Umbria’s rolling landscape, Italy’s "Green Heart"

  • Discover the medieval town of Assisi, a UNESCO World Heritage Site and home of St. Francis

  • Enjoy gracious boutique hotels with distinct regional flavor, boasting their own wineries

Vast rolling hills in Tuscany's Val d'Orcia

The rolling hills, vineyards, and medieval villages in Val d'Orcia

Renaissance landscapes of Val d'Orcia

This vast, undulating valley is a UNESCO World Heritage site. You'll quickly fall in love with this idyllic rural landscape much admired and painted by Renaissance artists.

What Guests are Saying
A group of people posing in front of a Tuscany landscape

This bike tour takes you to two stunningly beautiful regions of Italy. Umbria, often underestimated, showcases a vibrant local culture, unique artistic heritage, and untouched natural beauty. Southern Tuscany, with its picturesque landscapes painted with earthy and warm tones, has a mesmerizing allure. Come and discover for yourself this authentic Italian paradise that has stolen my heart away.

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Susy Maddalon, Trip Designer

Sara and Angelo our guides are phenomenal humans and amazing guides – they ensured we enjoyed the trip of a lifetime! We were already very loyal to Trek on the bicycle side, and now Trek Travel will be our go-to cycling trip provider! Everything was perfect and they both worked very hard to provide a very special experience.

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Liz A., Trek Travel Guest

Two Cyclists riding by the camera in Tuscany, Italy

We couldn’t have loved it more! From the expert guides to spectacular bikes, this was definitely a trip of a lifetime! We were referred by friends for this trip and it exceeded our expectations. Thanks Trek Travel!

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Linda S., Trek Travel Guest

A female cyclist in Tuscany, Italy

This is my 5th Trek Travel Trip. With every trip, I say, “Wow, this is the best trip yet!” I’ve encouraged quite a few friends to try Trek Travel and they too are now repeat customers. The trip itineraries are perfect. The cycling amazingly beautiful and perfectly (did I really just say that?) challenging. But please know, your guides make these trips. I’m not sure how they are chosen; what the interview process is. But you nail it every time.

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Allie Z., Trek Travel Guest

Great Ride

Ride to the hilltop jewels of Pienza and Montepulciano

Pedal ribbons of pavement through rolling hills and vineyards to the Renaissance splendor of these impressive, perched towns.

Dates & Pricing

Book early for the best price

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability