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Tuscany Hiking Tour – Chianti, Val d’Orcia & Crete Senesi with Guide

Scenic trails, castles & winery landscapes

Discover the beauty of Tuscany with our Tuscany Hiking Tour.
Choose your route through Chianti, Montalcino, Crete Senesi, or Val d’Orcia, accompanied by a knowledgeable local guide who will reveal the history, secrets, and natural wonders of the area. Along the trails, admire ancient castles, wineries, and churches, and pause to soak in the ever-changing colors of the Tuscan landscape.
For those who wish, upgrade the experience with a scenic picnic, a local trattoria lunch, or a wine-paired meal at a winery, turning your hike into a full day of discovery and flavor.

Tour Highlights what makes this tour unique

  • Scenic Hiking Trails: Walk through Chianti, Montalcino, Crete Senesi, or Val d’Orcia.
  • Cultural Landmarks: Discover castles, wineries, and historic churches along the way.
  • Local Expertise: Enjoy insights and stories from your English-speaking hiking guide.

Tour Overview a classy touch

  • Pick-up and drop-off at your hotel
  • Private hiking tour with flexible itineraries
  • English-speaking local guide for the full day
  • Traditional lunch in a local farm or winery

about us

a kind of family business…

Over 15 years of experience in wine, gastronomy, and bespoke travel design.

Niccolò is our wine and tour expert, with deep knowledge of Tuscany’s terroirs and producers, curating experiences defined by refined access and local insight.

Alexandra, a top-rated chef, personally leads and oversees our cooking experiences, ensuring professional standards, storytelling, and authentic Tuscan cuisine throughout.

We are supported by a dedicated team of experienced travel designers and trusted driver-guides, allowing us to deliver seamless execution, discretion, and the level of service expected by luxury travelers and their advisors.

Your Questions Answered

The Val d’Orcia & Chianti Hiking Tour is a scenic guided trek through Tuscany’s iconic landscapes, combining walks in the rolling hills of Val d’Orcia and Chianti with breathtaking views and cultural insights.

This tour is suitable for moderately active participants. Trails vary from gentle walks to more challenging paths, so comfortable hiking shoes and a good fitness level are recommended.

You’ll enjoy panoramic views of vineyards, olive groves, cypress-lined roads, and medieval villages unique to Val d’Orcia and Chianti, with plenty of opportunities for photos and local storytelling.

We recommend comfortable clothing, sturdy hiking shoes, sun protection, and water. Layered clothing is suggested for changing temperatures.

Outdoor activities depend on weather conditions. In case of rain or unsuitable weather, we can arrange an alternative Tuscan experience such as a private wine tour with tastings or a cultural visit, ensuring you still enjoy a memorable day.

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Tuscany Hiking Tour – Chianti, Val d’Orcia & Crete Senesi with Guide

Starting from

€ 250

Starting from
€ 250
Tuscany Hiking Tour – Chianti, Val d’Orcia & Crete Senesi with Guide
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