Walking Adventure Tours & Trips in Tuscany

You'll walk sections of the Via Francigena pilgrimage route through rolling countryside from San Gimignano to Montauto, about 2.5-3 hours through vineyards. Walk atop San Gimignano's medieval walls for views of the hills and towers, plus take orientation walks through Siena's historic center.

See UNESCO-listed Pienza before enjoying wine tasting in hilltop Montepulciano, famous for local pork, cheese, and honey production. Walk through medieval Siena's Torre del Mangia and il Campo during an orientation tour. Tour Florence's iconic Ponte Vecchio and Duomo on a guided walking tour, then visit the bustling Mercato Centrale with your CEO before ascending to Piazzale Michelangelo.

Start at Pisa's Leaning Tower and ride 45 km along the Monti Pisani to Lake Massaciuccoli's quiet shores. Renaissance villas dot the hills around Lucca, and Collodi's where you'll find Pinocchio's legacy in well-kept gardens, then pedal through Montecatini Terme's Belle Époque spa district before reaching Florence.

Spend 7 days on self-guided hikes through Tuscany's Crete Senesi region, walking 10 to 22 kilometers daily between medieval villages like Asciano and Trequanda. Stop in UNESCO-listed Pienza to try pecorino cheese and truffles, then head to Montepulciano for wine tasting while staying in 3-star hotels.

Walk 11km through Chianti vineyards from Florence to Greve, staying in medieval towns like Castellina in Chianti with its old defensive walls. Try wine tasting while hiking past cypress trees and cornfields through Panzano, an Etruscan-era village, then continue 16km on Via Romea.

Walk the UNESCO-listed Val d'Orcia on old pilgrimage routes, hiking past the famous Vitaleta chapel with its cypress trees and through vineyards that produce Brunello di Montalcino wines. The Via Francigena trail takes you from San Quirico d'Orcia to hilltop Montalcino, covering 13 kilometers.

Trek the UNESCO-listed Val d'Orcia's Gladiator Trail from Pienza past the Romanesque Corsignano church through cypress-dotted hills. Walk cypress-lined paths of the Via Francigena from Abbadia a Isola to Colle Val d'Elsa, then hike medieval Monteriggioni's ancient walls. Sample pecorino and ricotta cheeses paired with Montepulciano wine after checking out Renaissance Pienza commissioned by Pope Pius II.