Castiglione del Lago + Isola Maggiore

Depart villa via SS71 south and west around Lake Trasimeno. The approach to Castiglione del Lago along the lake causeway is scenic. 25–30 minutes.

Arrive Castiglione del Lago. Park at the main car park on the causeway approach (free or nominal). Walk through the medieval gate into the historic centre.

Palazzo della Corgna + Rocca del Leone (combined ~€5): the 16th-century ducal palace with Mannerist fresco cycle across multiple ceilings and walls — a genuinely underrated ensemble. Then cross the covered passageway to the Rocca del Leone for the panoramic view over the lake and the three islands. Allow 1–1.5 hours.

Walk the promontory walls: the exterior circuit offers continuous views over the lake on three sides. 30 minutes.

Walk to the ferry dock (Lungolago Giacomo Matteotti, 5 minutes from the historic centre). Board the ferry to Isola Maggiore (~€10–13 return; verify current schedule and fare at the dock).

Arrive Isola Maggiore. Walk the single main street (Via Guglielmi) — the entire island takes 30–40 minutes to walk through. Church of San Salvatore (13th century, free) at the hilltop; the Chapel of Sant'Antonio (marking Saint Francis's Lent fasting site, 1211) at the island's north point; lacemaking (tombolo) sold from houses along the street.

Return ferry to Castiglione del Lago. Depart on the next scheduled crossing.

Lakeside passeggiata: the Lungolago promenade along the lake shore below the town walls, with views toward the islands and the Umbrian hills. Café culture. Ice cream. Swimming is possible at accessible bathing areas along the shore (water stays warm into October).

Optional: bike hire (Cicli Valentini or similar in town) for a 1-hour cycle along the flat lakeshore path — one of the easiest and most pleasant rides on the itinerary.

Depart Castiglione del Lago for Cortona. Estimated return 5:30 PM direct; 7:00 PM if the full afternoon is enjoyed at the lake.