We meet on Crete in Chania (3 nights), an easy hop from Athens. There’s time for a light walk and a chance to browse the covered market. From Chora Sfakion, we take a boat ride along the coast to Agia Roumeli, where we meet up with local fishermen and then walk a breathtaking stretch of the Samaria Gorge. We’ll stroll the beautifully-preserved village of Heraklion (1 night), studded with Venetian and Ottoman architecture. From Arkadi, we walk through flocks of sheep, rolling hills and olive groves to the excavations of ancient Eleftherna. With water bottles filled from a mountain spring, we enter the awesome Kourtaliotiko Gorge and explore the monastery at Preveli.

After a memorable visit to the Minoan Palace of Knossos, we journey across the sea to Santorini. In Oia (2 nights), we wind through ancient streets to explore and shop, visit artisans and craftmakers, or just linger poolside at our hotel. Next day, a morning walk on the slopes of the famous volcano precedes an invitation to a local vineyard for a tour and tasting with views of sunset over the crater.