Who is this Itinerary For?
This 6-day Greek island sailing adventure is crafted for friends, couples, or small groups seeking an intimate exploration of the Northern Dodecanese. Trade crowded tourist spots for serene coves, authentic island life, and the freedom of the open sea. It’s for those who appreciate hidden gems, fresh seafood, and waking up to a new horizon each day.
Detailed Itinerary
Day 1: Embarking in Kos & Sailing to Kalymnos
Upon embarking in Kos, and after a brief orientation, set sail for Kalymnos. Enjoy a quiet bay for an onboard lunch and a refreshing swim. Continue to Vathys, a dramatic fjord-like entrance opening into a picturesque fishing village. This lush valley, rare for the arid island, boasts its own spring water. Tonight, savor dinner at Bootshaus Old Poppy’s Taverna, a local favorite known for its exceptional chef.
Day 2: Leros’ Secluded Bays
Begin your day with a refreshing swim in Vathys’ natural ocean pool. Then, set sail for Leros, an island beloved for its quiet anchorages. Find a remote, tranquil bay for a night under the stars. Enjoy a barbecue prepared onboard, paddleboarding in the calm waters, and the pure freedom of living off-the-beaten-path on your sailboat.
Day 3: Lipsi’s Blue-Domed Charms
Journey to Lipsi, an untouristy village famed for its numerous blue-domed churches. Wander through whitewashed buildings adorned with vibrant bougainvillea. Take a short walk to a lovely sandy beach or hike to the headland for spectacular sea views. If conditions permit, a swim stop at Macro Nisi offers dramatic cliffs and a unique snorkel through a semi-submerged tunnel.
Day 4: Patmos, The Holy Island
An early start brings you to Patmos, the renowned Monastery Island. Explore the 10th-century Monastery of St. John, an active and influential part of island life. Discover Chora, the village at its base, with its narrow winding alleyways and traditional charm. Experience the peaceful dawn as locals go about their day, offering a glimpse into authentic island rhythm.
Day 5: Kalymnos’ Hidden Pirate Bay
Sail back towards Kalymnos, aiming for a night on anchor in a tranquil bay near Emporios, or perhaps a secluded “Pirate Bay.’ This hidden oasis, accessible by dinghy, offers a unique escape with its own small bar and restaurant, providing a perfect, off-the-main-track Greek island experience.
Day 6: Return to Kos & Farewell
Enjoy a final morning swim before setting sail for Kos. Stop for lunch and a swim at one of the uncrowded bays around Kalymnos or Pserimos, perhaps hiking the hills to pick fragrant sage. Upon arrival in Kos, enjoy the comforts of land-based facilities. Conclude your unforgettable sailing adventure with a celebratory dinner at a gorgeous beachfront restaurant.
