Tuscany (Toscana) is one of Italy's most celebrated regions, renowned for its breathtaking landscapes of rolling hills, cypress-lined roads, and vineyards, as well as its extraordinary concentration of Renaissance art and medieval architecture. Home to Florence, Siena, and Pisa, Tuscany gave the world Dante, Leonardo da Vinci, Michelangelo, and the foundations of the Italian language.
Top trails
Routes worth lacing up your boots for.
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1
Via Francigena
The ancient pilgrimage route from Canterbury to Rome passes through the heart of Tuscany, linking Pontremoli, Lucca, San Miniato, San Gimignano, Siena, Bagno Vignoni, and many hill towns. Well-waymarked with yellow-and-white signs, with pilgrim accommodation (ostelli) en route.
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2
Chianti Wine Trail (Radda to Volpaia)
A beautiful walk through the heart of the Chianti Classico wine zone, from the medieval village of Radda in Chianti to the tiny fortified hamlet of Volpaia, passing through vineyards, olive groves, and oak woodland. An absolutely classic Tuscan landscape walk.
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3
Crete Senesi Landscape Walk
The crete senesi (Sienese clays) is an otherworldly landscape of eroded pale clay hills south of Siena, dotted with lone farmhouses, cypress groves, and ancient abbey. Walking through this unique landscape - especially in spring when wheat turns it vivid green, or autumn when it glows golden - is one of Tuscany's great experiences.
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4
Val d'Orcia Walk (San Quirico d'Orcia to Pienza)
A beautiful and manageable walk through the UNESCO-listed Val d'Orcia landscape, linking the medieval village of San Quirico d'Orcia with the Renaissance gem of Pienza. The route passes through classic Tuscan countryside of rolling hills, cypress trees, and farmhouses.
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5
Monte Amiata Summit Trail
Monte Amiata is an extinct volcano in southern Tuscany, rising to 1,738 meters - the highest point in Tuscany south of the Arno. Summit trails through beech forests and open ridgelines offer panoramic views over Tuscany, Umbria, and the Tyrrhenian Sea. A ski resort operates in winter.
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6
Garfagnana - Orrido di Botri Gorge
A spectacular gorge walk through the Orrido di Botri, a dramatic limestone canyon in the heart of the Garfagnana valley protected as a nature reserve. The path follows the Pelago stream through narrow gorges, over polished rock slabs, and through tunnels carved into the cliff face.
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7
Apuan Alps - Pania della Croce
The Apuan Alps above Lucca and the Versilia coast offer some of Tuscany's most dramatic mountain scenery, with sharp white marble peaks rising above the sea. Pania della Croce (1,858m) is the range's most popular summit, offering extraordinary views from the sea to the Apennines.
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8
Casentino Forest National Park Walk
The Casentino Forests National Park, on the Apennine border between Tuscany and Emilia-Romagna east of Florence, protects one of Italy's largest and most ancient forest areas. The landscape of silver fir, beech, and oak forests was where Francis of Assisi received the stigmata at La Verna monastery.
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9
Via Clodia - Maremma Coastal Walk
The Via Clodia follows the route of the ancient Roman road through the Maremma, the wild southern part of Tuscany, linking Etruscan and Roman sites including Saturnia thermal springs, Pitigliano, Sovana, and the coast. A unique combination of history, landscape, and wildlife.
Trail difficulty levels
Pick a route that matches your fitness and experience.
Mostly flat, well-marked paths. Suitable for families and casual walkers.
Some elevation gain, longer distances. Requires basic fitness.
Significant climbs and exposure. Requires good fitness and route-finding.
Technical terrain, scrambling, or alpine conditions. Experience essential.
Local hazards
What to watch out for on the trail.
Sudden weather changes — always carry rain gear and warm layers.
Wildlife encounters — make noise on the trail and store food properly.
Trail conditions can deteriorate after rain — check recent reports before setting out.