We're sailing a loop from Kos through several islands — each one quieter, stranger, and more interesting than the last. Flotilla of catamarans, professional skippers. No sailing experience needed. Just a willingness to haul a line and wake up early when the wind says so :)
Get to Kos Marina by 4 PM. Transfers from Kos International Airport (KGS) are easy. Settle into the catamaran, meet your crew and skipper, run through the safety briefing. Quick walk to the local market to stock up on Greek produce, wine, and everything we'll need for the week. Welcome dinner and sundowners at the marina while we map out the route.
→ Objective: show up, meet the crew, stock the boat.
An easy 9 nautical mile, 2–3 hour sail to Vathys Cove on Pserimos. Safety briefing, role assignments, provisioning split — then we cast off. Vathys is a protected anchorage with turquoise water and not much else. Swim, walk the shore, first dinner on board as the sun goes down.
→ Objective: remember what slow feels like.
A short 8 nautical mile sail (about 2 hours) to Kalymnos — limestone cliffs, sponge-diving history, and some of the best rock climbing in Europe. Optional intro climbing session or cave exploration on arrival. Sunset walk above Pothia harbor, then a group tavern dinner.
→ Objective: earn the orzo.
A sheltered 10 nautical mile (~3 hour) passage into Lakki, one of Greece's finest natural harbors. Leros is quiet, elegant, and full of unexpected WWII-era Italian architecture. Explore by scooter, hike up to Panaghia Castle for the views, or wander Agios Isidoros. Your call.
→ Objective: balance activity with doing absolutely nothing.
Expedition day. Early departure, 23 nautical miles, 4–5 hours across open water. This is where it starts to feel like real sailing. Arrive in Skala, then up to the Monastery of St. John — a UNESCO site perched on a volcanic ridge. We'll catch sunset from there.
→ Objective: move until the sea feels earned.
Gentler day. 10 nautical miles, 2–3 hours. Anchor stop in a bay where the water genuinely doesn't need a filter — swim, float, reset. Lipsi is small, non-touristy, and made for slow walks. Shared flotilla dinner ashore. Kayaks and paddleboards out for anyone who wants more water time.
→ Objective: let the group find its rhythm.
The big one. 32 nautical miles, 5–6 hours of focused sailing — the longest leg of the trip. Early mandatory departure. Expect a beam reach or a downwind run, watch rotations in full effect, everyone gets time at the helm. Hydration protocol: drink water, then drink more water. Refuel and dock in Kos. Final celebratory dinner, tales of the sea, toasts to new friendships.
→ Objective: finish strong.
Buffer day for relaxed checkouts and any weather delays. Revisit a favorite café, grab souvenirs, or just sit with the last of the island quiet before flying home.
→ Objective: leave lighter than you arrived.
Charter — Catamaran, skipper, insurance, all fees
Fuel & Ports — Covered
Provisions — Breakfasts and snacks on board
Dinners — Group tavern dinners on the islands
Wi-Fi — Unlimited internet device on board
Travel Insurance – for the complete length of the adventure
Flights — Getting yourself to Kos
Extras — Climbing guides, water sports, personal drinks
Single Cabin — Available on request at supplement
