Via Francigena: San Gimignano to Siena
Must-DoIconicThe medieval pilgrimage route passes through the heart of Chianti country. Rolling hills, stone farmhouses, and vineyards. Well-marked with accommodation in agriturismi along the way. 60 km total.
Val d'Orcia Loop from Pienza
Must-DoFamilyStart from Pienza and walk through the UNESCO landscape — lone cypress trees, golden wheat fields, and that perfect Tuscan light. Stop for pecorino at a farm. The most photographed landscape in Italy.
Apuan Alps: Monte Forato
Hidden GemAdvancedA mountain with a natural arch (hole through the peak) in the wild Apuan Alps above Versilia. Steep and rugged — a completely different side of Tuscany. Start from Cardoso village.
Chianti Wine Trail: Greve to Panzano
FamilyBudgetA gentle walk through Chianti Classico territory connecting two charming wine towns. Pass through vineyards and olive groves, stop for tastings at small estates. End in Panzano for Dario Cecchini's legendary butcher shop.
Parco della Maremma Coastal Trail
Hidden GemSouthern Tuscany's wild coast — Mediterranean scrub, sea cliffs, and abandoned watchtowers. Strictly limited daily visitors — book at the park office in Alberese. Closed June–August on hot days.
Our pick
Val d'Orcia loop from Pienza for the classic Tuscany experience. The Apuan Alps for something completely unexpected.