Sail in Kos - 8 Days

Welcome to your sailing adventure.

Board in the late afternoon and settle into your cabin at Kos Marina. Kos itself is worth arriving early for if your flights allow: the island was the birthplace of Hippocrates, and its old town mixes Roman ruins, an Ottoman-era castle, and palm-lined streets. The first night is spent quietly in the marina, getting to know the boat and crew before the sailing begins.

The first proper day of sailing. You cross to tiny Pserimos, a speck of an island whose main bay opens onto a wide, shallow stretch of sand and turquoise water — a perfect first swim stop. From there you continue to Kalymnos, famous as Greece's sponge-diving island and now equally renowned among rock climbers for its dramatic limestone cliffs. You'll moor near Pothia, the bustling main harbour, or in the green, fjord-like inlet of Vathi.

A shorter hop north to Leros, one of the most distinctive islands in the group. During the Italian occupation it was built up with striking Art Deco and Rationalist architecture, most visible in the planned harbour town of Lakki. The fishing village of Pandeli sits below a medieval castle that rewards the climb with sweeping views over the bay at sunset.

Sail to Lipsi, a small, low-key island that has stayed pleasantly off the mainstream route. Days here are about quiet beaches, clear swimming coves, and a relaxed village clustered around the port — the kind of place built for slowing down rather than ticking off sights.

The cultural high point of the trip. Patmos is where Saint John is said to have received and written the Book of Revelation. You can visit the hilltop Monastery of Saint John the Theologian — a UNESCO World Heritage Site — and the nearby Cave of the Apocalypse, then wander the whitewashed lanes of Chora, one of the best-preserved medieval towns in the Aegean.

A sail out to remote, all-but-uninhabited Levitha. There's no village here — just a single family who farm the land and run a small taverna, plus a sheltered natural harbour that protects boats from the open-sea winds. It's the most off-grid night of the week: dark skies, deep quiet, and a simple home-cooked meal ashore.

The longest sail of the week as you make your way back toward Kos, breaking up the passage with a stop in a secluded bay for a final swim and lunch at anchor. A last evening on board to enjoy the open water before returning to the marina.

Check out in Kos at 09:00. If you have time before onward travel, the Asklepion — the ancient healing sanctuary just outside town — is a fitting place to end a trip through these islands.