A week in the Dodecanese: The islands you’ll actually sail to

Two routes, one Dodecanese sailing holiday, decided on the day

SeaScape sails two main routes out of Kos: a northern route through the upper Dodecanese and a southern route toward the islands closer to Rhodes. Both are seven days. Both are exceptional. Which one we take on any given week is decided on the morning of departure, based on one thing above everything else: the Meltemi.

The Meltemi is the prevailing wind system that dominates the Aegean from June through September. A strong, dry northerly that can blow anywhere from a pleasant 15 knots to a very determined 40. It’s not a storm. It’s just Greece doing what Greece does. Understanding it is the difference between a comfortable sail and a day where everyone is gripping the rails. You can check current conditions via Windy, the same tool Paul uses when planning the morning’s route.

When the Meltemi is blowing hard in the northern Dodecanese, we like to head south. Calmer waters, more sheltered anchorages, guests who arrive at dinner having actually enjoyed the crossing. When the wind in the north is ideal, we go there. In the height of summer we also factor in temperature: the southern route can be genuinely hot in July and August, and sometimes the cooler northern air is exactly what the group needs.

We also ask the group. On a shareboat, eight people can have eight different preferences: some want maximum sailing, some want to swim off the boat all afternoon, some have a specific island they’ve always wanted to see. Finding the best route for everyone is part of what Paul does. On a private charter it’s simpler. The group decides together and Paul makes it happen. On either trip, his read of the weather conditions is always the final word. In rougher weather, an extra day in a sheltered harbour beats six hours of seasickness.

What this means for you as a guest: your week will be shaped by the weather, the wind, and the people you’re sailing with.

No two SeaScape Dodecanese sailing holidays follow exactly the same route. That’s the whole point.

The northern route highlights

Vathys, Kalymnos

Kalymnos is known for rock climbing. Vathys is Kalymnos’s quieter secret. A deep, narrow fjord on the island’s eastern side, surrounded by citrus orchards, with water clear enough that jumping off the boat is compulsory. There’s a cliff right next to the dock for anyone who wants to push their luck a little further, and the paddleboard makes a fine vessel for those who want to explore further along the shoreline.

Vathys has one dock, a handful of tavernas, and a pace of life that feels genuinely removed from the rest of the world.
We always eat at Poppy’s. The real one. A word of warning is necessary here: there are two tavernas near the dock, and one of them trades heavily on the reputation of the other. The original is BOOTSHAUS Poppy’s, a short walk from where we moor. It has been feeding SeaScape guests for years, and the welcome we receive there feels like family. Chef Antonios comes out of the kitchen personally to show you the day’s catch. Whole fish, laid out for you to choose from, before his father takes over at the outdoor grill. While the fish cooks, Antonios’ mother keeps the table looked after, making sure cold drinks keep coming. The food arrives with mezze, local wine and cold Greek beer, and the kind of unhurried generosity that makes you forget you’re on a schedule. Dinner at Poppy’s regularly runs until the small hours. Nobody minds. The more guests at the table, the bigger the fish. It’s that kind of place.

Archangelos

North of Leros lies one of the quietest nights of the whole trip. Archangelos is not a port. It’s an anchorage, tucked away from the wind, away from other boats, away from everything. We drop anchor, fire up the barbecue on the back of the boat, and spend the evening exactly there.

If you want to sleep outside under the stars, this is the night to do it. The sky in the northern Dodecanese away from any light pollution is the kind of thing people mention when they get home and try to explain what the trip was actually like. It’s easier to just show up and see it.

The southern route highlights

Chalki

Chalki is our personal favourite over the more famous Symi. Similar in feel, a fraction of the crowds. Pastel-coloured houses in Venetian style line the harbour, the kind of scene that takes you entirely by surprise after a day at sea. It’s a small fishing port, so we like to arrive early to secure a spot on the dock.

There are good bars and restaurants along the waterfront, a beach bar for a lazy afternoon, and a few small souvenir shops if that’s your thing, though nothing about Chalki feels touristy. For the early risers: get up before the rest of the boat and hike up to the 15th-century fortress of the Knights of St John. The views over the island from the top make the climb entirely worth it. For everyone else: coffee in the cockpit, a swim, and absolutely nowhere you need to be.

Pali, Nisyros

Pali is a tiny fishing village on the northern coast of Nisyros that you don’t really reach unless you arrive by boat. We dock right on the quay, which puts us about ten seconds from the Aphrodite restaurant.

Aphrodite has a full menu, but the right move is always the chalkboard. Daily specials only, written up that morning based on what’s fresh: goat stew, grilled calamari, pastitsio, whatever came in that day. Choosing is genuinely difficult. The food is straightforwardly excellent.

Pali is our base for the next morning’s highlight: a car up to the volcano crater of Nisyros, one of the most dramatic landscapes in the Aegean. You stand on the rim of an active caldera, the ground sulphurous and pale yellow beneath you, the Dodecanese spreading out in every direction. It’s a long way from the boat, in the best possible sense.

A note on arriving: Med mooring

If you’ve sailed in the Caribbean or on a flotilla holiday with mooring balls, docking in Greece will be a new experience. The standard method throughout the Dodecanese is Mediterranean mooring: we drop anchor as we approach the quay, reverse the boat in a straight line toward the dock, attach our lines, and then tighten the anchor chain to hold everything in place. It requires precision and a good read of the wind, two things Paul has in abundance.

Guests are welcome to help. Taking a line, helping with the fenders… None of it requires much experience, and all of it makes you feel like part of the crew. Some guests spend the whole week learning the process. Others watch from the cockpit with a cold drink. Both are entirely valid.

What doesn’t change

Routes change. Islands swap in and out. Weather makes its own decisions. What stays constant on every SeaScape Dodecanese sailing holiday is the knowledge behind every route decision. Which anchorage offers the best shelter tonight, which taverna has been worth the walk for years, which crossing is best done early before the wind builds. Thirty years of SeaScape history sailing the Dodecanese is baked into every choice Paul makes.

The islands you’ll visit on your week will be the right ones for that week. That’s the only guarantee we make, and in our experience it’s the only one that matters. Browse available weeks and start planning your Dodecanese sailing holiday below.

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