Walking Adventure Tours & Trips in Central Italy

Walk the Via Francigena pilgrimage route to UNESCO-listed San Gimignano with its 14 medieval towers, then head to Castello La Leccia organic winery for Chianti Classico tastings. Take the iconic Vitaleta chapel path from Pienza through Val d'Orcia's cypress-lined hills, finishing with Brunello di Montalcino wine sampling in this hilltop town at 500 meters elevation.

Walk the historic Via Francigena pilgrimage route from Abbadia a Isola to Colle Val d'Elsa, where ancient stone farmhouses and cypress-lined paths wind through Tuscany's rolling countryside. Trek the UNESCO-listed Val d'Orcia's Gladiator Trail from Pienza to the exact spot where Ridley Scott filmed.

Trek the UNESCO-listed Val d'Orcia and walk the Gladiator Trail near Pienza, where Ridley Scott filmed those famous countryside scenes. You'll stay 7 nights in hotels and 2 nights in traditional agriturismos while walking through medieval Monteriggioni and crossing the Elsa River ankle-deep.

Stay 5 nights at Casa Florelia agriturismo and walk the Via Francigena pilgrimage trail through vineyards for 2.5-3 hours of countryside trekking. Check out San Gimignano's medieval walls, Volterra's Etruscan heritage and alabaster workshops, then take guided walks through Florence and Siena.

Walk through Pienza's cobblestone streets, a UNESCO site in Tuscany, then head to medieval Montepulciano for a tasting of the famous Vino Nobile wine. In Florence, you'll stroll across the Ponte Vecchio and climb up to Piazzale Michelangelo for views over the Arno River and city below.

Ride through Pisa's UNESCO-listed Piazza dei Miracoli, then follow the Serchio river north to Lucca where Renaissance walls still stand intact. You'll check out Collodi's whimsical Pinocchio Park and Villa Garzone gardens, pedal through Pescia's famous flower markets, then finish in Florence.

Cover 109 kilometers over 7 days from Buonconvento to Chiusi, with daily ascents between 236 and 909 meters across rolling Tuscan terrain. Pass through medieval Chiusure and Petroio, a cone-shaped hamlet at 487 meters built from golden sandstone, then continue along gravel roads with views.

Follow the Via Romea pilgrimage trail from Florence to Siena, walking past the UNESCO medieval towers of San Gimignano and the fan-shaped Piazza del Campo. Check out Volterra's Etruscan burial sites and alabaster workshops, then head along the Via Sale salt trade path to the coast.