Stroll
Tuscany

Tuscany

Tuscany

Walk one of Europe's most iconic landscapes, following ancient pilgrimage paths and vine-lined tracks through the rolling hills, medieval hill towns and sun-drenched vineyards.

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Overview

Few regions in the world reward walkers quite like Tuscany. Cypress-lined ridges, terracotta-roofed villages and vineyards stretching to the horizon form a landscape that has inspired artists and travellers for centuries. Our walks thread through the Chianti winelands and connect some of the region's finest hilltop towns, from the towers of San Gimignano to the medieval grandeur of Siena and the UNESCO-listed beauty of the Val d'Orcia. The walking is gentle and unhurried, leaving plenty of time for long lunches, Chianti in hand, and evenings in a hilltop village that are impossible to forget.

30+ Years Experience
Pack-Free Walking
24/7 Support

The Tuscany Experience

Wonder
Stroll from Etruscan Volterra to Montepulciano through UNESCO-protected Val d’Orcia region
Step into San Gimignano’s UNESCO-listed centre beneath its medieval tower skyline
Explore Siena’s glorious Piazza del Campo and Monteriggioni’s ancient ramparts
Wellness
Moderate walks along strade bianche, vineyards and gently rolling Senese landscapes
Soak in Bagno Vignoni’s thermal baths after walking from Sant’Antimo Abbey
Recharge in family-run boutique B&Bs, classic townhouses and rural hotels
Nature
Follow cypress-lined white roads through Brunello vineyards and chestnut groves
Picnic beneath olive trees near Poggio Alloro and Poggio Casaglia
Sunset over the Val d’Orcia from Montepulciano’s hilltop edge

What you'll eat


Pecorino Cheese
Salty sheep’s milk cheese from Pienza, best with bread and views
Gelato
A slow afternoon scoop in San Gimignano’s buzzing piazzas and cobbled lanes
Tuscan Breakfasts
Buffets of local cheeses, pastries and fruit before setting out walking

Where you'll stay


Family B&Bs
Small family-run stays chosen for history, location and an easy welcome
Medieval Stone Inns
Stone walls, timber beams and terracotta floors give nights real Tuscan character
Villa Stays
Neoclassical villas and traditional houses with frescoes, gardens and old-world calm

How you'll travel


Private Transfers
Taxis bridge selected route sections, making longer logistics feel smooth and simple
Luggage Shuttles
Your bags move ahead each day, leaving you free to walk light
Pilgrim Paths
Follow stretches of the Via Francigena through cypress avenues and hill towns

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