Naples

Why it matters: run by young people from the Quartieri Spagnoli through the San Nicola da Tolentino social cooperative (a 2014 spin-off of the same La Paranza group behind the Catacombs of San Gennaro), this guesthouse funds job training and neighborhood programs for local youth. The setting seals the deal: a 17th-century monastery with a 5,000-square-meter garden that’s a protected national monument, sweeping views of Vesuvius and Capri from the rooftop, and a resident staff who’ll walk you through the Spanish Quarter’s alleys themselves. Book a sea-view room and ask staff about their neighborhood tour.