Home > Italy > Tuscany

Tuscany Walking holidays

Experience the charm of Tuscany on a breathtaking walking holiday through rolling vineyards, medieval villages, and sun-kissed landscapes. Wander along scenic trails past cypress-lined roads, olive groves, and historic towns like San Gimignano and Siena. Immerse yourself in the region’s rich history, world-class cuisine, and stunning countryside for an unforgettable adventure.

  • Personalized quotation

  • 24h travel assistance

  • Luggage transfers

  • Selected accommodations

Walking holidays in Tuscany

Tuscany
Classic Tuscany Short Break

Let yourself be carried away by the natural and gastronomic charms of the Tuscany region.

5 Days From 1,142 CAD
More information
Tuscany
Classic Tuscany Walk

Live a unique and relaxing experience as you immerse yourself in the best of Tuscany.

8 Days From 2,163 CAD
More information
Tuscany
Volterra to San Gimignano Walk

Discover the magic of Tuscany on a tour of its vineyards and medieval villages.

9 Days From 2,616 CAD
More information
Tuscany
Florence to Siena Walk

Explore the medieval and Renaissance period in beautiful and unmissable Tuscany.

8 Days From 2,176 CAD
More information
Tuscany
Tuscany Hill Walks | 6 days

Explore the medieval and Renaissance period in beautiful and unmissable Tuscany.

6 Days From 2,655 CAD
More information
Tuscany
Chianti Classic Walk

Explore the Chianti region among hills, sunflowers and endless vineyards.

11 Days From 3,370 CAD
More information
Tuscany
Tuscany Hill Walks | 8 days

Enjoy the charm of southern Tuscany, one of the most beautiful regions in Italy.

8 Days From 2,657 CAD
More information

Why Tuscany?

  • Rolling Tuscan Landscapes – Walk through breathtaking countryside filled with rolling hills, vineyards, and olive groves, capturing the essence of Tuscany’s timeless beauty.
  • Culinary Delights – Indulge in Tuscany’s rich culinary heritage, savoring local specialties such as pecorino cheese, fine wines, and traditional dishes in charming trattorias.
  • Historic Hilltop Towns – Explore medieval hilltop towns like San Gimignano, renowned for its well-preserved towers and rich history, offering a glimpse into Tuscany’s past.

Tuscany: Walk Through Timeless Beauty

Discover the charm of Tuscany on foot, where rolling vineyards, medieval hilltop towns, and cypress-lined trails create a truly unforgettable walking experience. Wander through the Chianti countryside, explore the historic streets of Siena and San Gimignano, and take in breathtaking views of golden fields and olive groves.

This enchanting region blends rich history, world-class cuisine, and stunning landscapes, making every step a journey through Italy’s cultural heart. Whether you’re drawn to the picturesque villages or the peaceful countryside, Tuscany offers the perfect mix of adventure and relaxation.

Let Orbis Ways take care of the details while you embrace the beauty of Tuscany. Ready to walk through Italy’s most scenic landscapes? Start your journey today!

Why Choose Orbis Ways ?

Find Your Ideal Trip

Explore over 200 carefully designed routes tailored just for you.

Tailor-Made Budget

We adapt to your needs to provide you with the best possible experience.

Get the Most Out of Your Trip

Join the Orbis Ways community and embark on an unforgettable adventure.

Thousands of travelers trust us