Tenuta San Masseo

Walking the vineyard paths at Tenuta San Masseo starts most days here, whether guests are heading to a tasting, a picnic among the vines, or a lesson in pressing the estate's own olive oil. The resort sits in a two-hectare park above Assisi, and its seven suites and rooms, ranging from 28 to 45 square metres, look out over the valley to the Basilica of Saint Francis. Rooms are named for local olive varieties: Moraiolo, Leccino, Cardinale, Frantoiano. The Frantoiano Charme opens onto its own terrace with a direct line of sight to the city. A private spa on the grounds includes a hammam and sauna, and there is a pool for guests staying on-site. Activities lean into the land itself: truffle hunting with dogs, guided treks up Subasio mountain, horse rides along the Way of St Francis, and e-bike routes through the surrounding hills and lakes. Cooking classes and pasta-making sessions run in the garden facing the Basilica. For events, the Masseo Vista Cube, a glass pavilion that opens fully to the park, holds up to 300 guests in winter and more in summer, giving weddings and galas a fixed view of Assisi regardless of weather. The estate is a 14-kilometre drive from Assisi's airport, with private parking on-site.