Seasoned hikers can conquer the 23.7 km stretch of the via Francigena leading from San Miniato to Gambassi Terme in under six hours, but why not make the fun last a bit longer? Transform an otherwise-challenging walk into a relaxing but still active weekend of exploration: take it slow, stopping off to see a mix of historic sites along the pilgrimage road—hospitality and monastic complexes, castles—and spots with appeal for today’s traveler—spas, excavation sites, eateries.