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Route · 14 days · one-wayYacht charter route · Dodecanese

Kos via 14 days.

Round-trip from Kos through Kalymnos, Patmos, Astypalaia, Nisyros, Rhodes and Symi: two weeks across the wilder, quieter islands of the Dodecanese.

The route

Day-by-day route

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Kalymnos
Day 1

Kos Marina → Kalymnos

A gentle 15-mile hop north to get the crew settled, with sponge-diving history in Pothia and limestone cliffs across the water.

Distance

15 NM

Sailing

~3h at 5 kn

At a glance

Route at a glance

Best season

May – mid-October (peak Jun – Sep)

Duration

14 days

Departure

Kos

Sailing area

Dodecanese

Route summary

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Day-by-day journey

Named anchorages, mooring notes and things to do for every leg of the week — the map follows along as you scroll.

Day 1 / 14
Kalymnos
1
Day 1

Kos Marina → Kalymnos

The first leg is short on purpose. Fifteen miles due north gives everyone time to find the winch handles and remember which line does what before the wind builds in the afternoon. Pothia, on the south coast, is the working town most crews tie up in: sponge boats, a decent fish market, and the Sponge Diving Museum tucked back from the quay. Look west and you'll see Telendos rising out of the channel, its climbing routes drawing people from all over Europe each October. If you fancy a swim rather than a town night, Vathy on the east coast folds back into a narrow green inlet that stays flat in almost any breeze. We usually settle for an ouzeri table and a plate of mououri, the local stuffed squid, before an early night.

Things to do

Tour the Sponge Diving Museum in Pothia

Swim the sheltered green inlet at Vathy

Watch climbers on Telendos across the channel

Order mououri stuffed squid at an ouzeri

Mooring tip

Go stern-to on Pothia quay, roughly €30–50 a night; the harbour fills with local boats so aim to arrive by mid-afternoon. For a quiet night at anchor instead, Vathy's inlet on the east side holds well in most conditions.

Leros
2
Day 2

Kalymnos → Leros

Leros gives you two very different overnights, and the wind usually makes the choice for you. Lakki, on the south side, is one of the biggest natural harbours in the Mediterranean, a huge protected basin lined with 1930s Italian Art Deco buildings that feel oddly grand for a small island. It holds flat even when the meltemi is honking. Agia Marina, on the north coast, is prettier at the waterfront but takes the north wind on the nose once it gets above twenty knots. Ashore, the climb up to Panteli castle repays the effort with a view over both harbours at once. Down at Xerokambos there's an easy swim beach on the south coast. Order pitaroudia, the local chickpea fritters, at a quay taverna and you'll understand why crews linger here.

Things to do

Walk the 1930s Art Deco quay at Lakki

Climb to Panteli Castle for the view

Swim the south-coast sand at Xerokambos

Try pitaroudia chickpea fritters at a taverna

Mooring tip

Lakki Marina takes you stern-to on lazy lines for around €40–60 and stays calm in almost anything. Agia Marina's town quay is cheaper at €25–40 but gets rolly once the north wind pushes past twenty knots, so read the forecast before committing.

Patmos
3
Day 3

Leros → Patmos

Patmos carries its history lightly for such a holy place. Skala, the port, has a long quay with good shelter from the north, so most crews tie up there and then head uphill. The road to Chora passes the Cave of the Apocalypse, where St John is said to have received his visions, before reaching the fortress-like Monastery of St John, an eleventh-century UNESCO site that still functions as a working community. The whitewashed lanes of Chora reward an hour of aimless wandering, ideally with a mastiha cocktail at the end of it. If the crew wants sand, Psili Ammos on the south coast is a golden-sand cove reached on foot or by tender. Evenings on the quay are quiet and unhurried, which is exactly the point of coming this far.

Things to do

Visit the Cave of the Apocalypse

Tour the 11th-century Monastery of St John

Wander the white lanes of Chora

Tender to golden-sand Psili Ammos beach

Mooring tip

Skala's quay is long and well protected from the north, with stern-to berths around €30–50. Space is rarely a problem, but tie up before the afternoon ferries start their shuffle if you want a settled spot.

Fourni
4
Day 4

Patmos → Fourni

This is the leg that takes you out of the crowds. Fourni sits in the channel between Ikaria and Samos, a scatter of small islands that once sheltered pirates and now shelters almost nobody. Twenty-four miles northwest brings you to Fourni Korseon, the one harbour with a proper quay and good cover from the north. Few charter boats push this far, so the waterfront still runs on its own rhythm: fishermen mending nets, one or two tavernas, a craftsman or two carving wooden boat models. Ashore, the walk up to the Christos chapel gives you the whole archipelago laid out below. Petrokopio, reachable only from the water, is worth the tender ride for a swim. In the evening, order astakomakaronada, the lobster pasta the islands are known for, and let the day slow right down.

Things to do

Hike to the Christos chapel viewpoint

Tender to Petrokopio Bay for a swim

Eat astakomakaronada lobster pasta at Kambi

Buy a hand-carved wooden boat model

Mooring tip

Fourni Korseon is the only practical overnight, stern-to on the quay for about €20–30 and sheltered from the north. If it's full or you want to swim off the boat, drop the hook on sand in Kambi Bay in four to six metres.

Lipsi
5
Day 5

Fourni → Lipsi

Lipsi runs at a walking pace and asks you to do the same. Around seven hundred people live here, served by a single bakery and a square with one church clock tower, and the waterfront tavernas are the sort where the owner cooks what the boats brought in that morning. The town quay is the only place to tie up, stern-to and well covered from the north. Come morning, it's worth motoring the two miles east to Aspronissi, where the water over the sand turns an almost unreal blue and the snorkelling is the best on the route so far. Back in town, ask for lipsiako cheese drizzled with thyme honey, and grab a bag of fresh koulouria from the bakery before the day-boats clear the shelves. There is nothing to rush toward, and that's the appeal.

Things to do

Snorkel the blue water at Aspronissi Bay

Walk out to the Panagia chapel rock

Try lipsiako cheese with thyme honey

Buy fresh koulouria from the village bakery

Mooring tip

The town quay is your only berth here, stern-to for a modest €15–25 and sheltered from the north. It's small, so arrive early in season; if the swim is calling, anchor on sand off Aspronissi Bay instead.

Levitha
6
Day 6

Lipsi → Levitha

Levitha is as remote as this trip gets. Six people live on the whole island, there's no ferry, no ATM and no shop, and one goat-herding family runs the single taverna above the anchorage. You come here for the emptiness. Ammoudi Bay bites deep into the south side and holds you on sand in five to seven metres, tucked well out of the north wind, and by evening yours may be one of only a handful of boats swinging on the hook. Walk up to the farm, lend a hand with the goats if the family will have you, and settle in for astakomakaronada cooked by the same people who caught the lobster. Then stay on deck after dinner. With no lights for miles, the star field overhead is the reason skippers remember this night for years.

Things to do

Anchor and swim in Ammoudi Bay

Help the family herd their goats

Eat lobster pasta at the island's only taverna

Stargaze on deck with zero light pollution

Mooring tip

There's no charge and no marina here: anchor on sand in Ammoudi Bay in five to seven metres, fully sheltered from the north. Bring enough cash and provisions, because there is no ATM and no shop on the island.

Palaia
7
Day 7

Levitha → Astypalaia

Astypalaia marks the far western corner of the Dodecanese, and it feels more Cycladic than its neighbours, all white cubes and blue domes. The overnight is Pera Gialos, the harbour below the kastro on the eastern side, sheltered from the north and within walking distance of everything worth seeing. Above it sits the Querini castle, a Venetian fortress the whole town seems to lean into; the climb up through Chora at dusk is the thing to do here. For a swim, Vatses on the south coast mixes sand and pebble under low cliffs. Food-wise, the drive out to Kaminakia taverna for ladenia, the island's tomato and onion flatbread, is a small pilgrimage crews rarely regret. History buffs can hunt down the Roman mosaics near Mesa Nisi. It's a satisfying halfway marker before the run to the volcano.

Things to do

Climb through Chora to the Querini castle

Swim the sand and pebble at Vatses

Eat ladenia flatbread at Kaminakia Taverna

Find the Roman mosaics near Mesa Nisi

Mooring tip

Pera Gialos takes you stern-to for around €25–40, tucked in below the castle and protected from the north. If the harbour is busy or the wind swings, Maltezana on the south coast is a calm anchoring alternative.

Nisyros
8
Day 8

Astypalaia → Nisyros

Today is the longest single hop of the fortnight, thirty-eight miles on a beam reach if the meltemi cooperates, so we usually slip the lines by nine. Nisyros is the payoff: a genuinely active volcano, and the walk across the caldera floor to the Stefanos crater is unlike anything else on this route. You descend into a wide grey bowl that hisses steam and smells of sulphur, with the crust crackling underfoot. Pali, on the north coast, is the harbour to aim for, sheltered from the north and an easy base for the trip inland. Wander the cobbled lanes of Mandraki afterwards, or soak tired legs in the Loutra thermal springs. Pick up a jar of the island's capers on the way back to the boat; grown in volcanic soil, they carry a punch you won't forget in a hurry.

Things to do

Walk into the steaming Stefanos crater

Wander the cobbled lanes of Mandraki

Soak in the Loutra thermal springs

Buy volcanic-soil capers to take home

Mooring tip

Pali on the north coast is the settled choice, stern-to for about €25–35 and sheltered from the north. Mandraki on the west side is closer to the sights but smaller and exposed when the wind has any northwest in it.

Tilos
9
Day 9

Nisyros → Tilos

Tilos wears its green credentials openly: it runs on solar and wind, and plastic bags have been banned here since 2018, making it the first island in Greece to go zero-waste. After the volcano, the fifteen miles east feel like a gentle recovery leg. Livadia, on the east coast, is the harbour, sheltered from the north and quiet in the evenings. The set-piece here is Mikro Chorio, a nineteenth-century village that emptied out decades ago and now flickers back to life on summer nights as a single hilltop taverna and bar among the ruins. Go up for a late drink and the atmosphere does the rest. By day, the hike to the Agios Panteleimon monastery is the classic walk, and the island's small wineries are turning out organic bottles worth a tasting. Try mizithra cheese with thyme honey at a village kafeneio.

Things to do

Drink among the ruins at Mikro Chorio

Hike to Agios Panteleimon monastery

Taste Tilos organic wine

Try mizithra cheese with thyme honey

Mooring tip

Most crews tie up stern-to at Livadia on the eastern shore, around €20–30 a night and tucked away from northerlies. Prefer to lie at anchor and swim? Head for Eristos Bay, a wide sandy sweep on the south coast.

Chalki
10
Day 10

Tilos → Chalki

Chalki is tiny and almost entirely car-free, home to some three hundred people who live around the horseshoe of Emporio harbour. The mansions ringing the bay were built by nineteenth-century sponge merchants, and the whole waterfront has been gently restored rather than rebuilt. Tie up stern-to on the Emporio quay, sheltered from the north. A short walk or motor east brings you to Pontamos, a cove where the water glows an almost artificial blue over pale sand, and the snorkelling there is the reason many crews divert to Chalki at all. Ashore, the climb up to the old Knights' Castle on the ridge gives you Rhodes on the horizon. For dinner, seek out pougia, the local sun-dried octopus, at Taverna Giorgos, and finish with a shot of souma, the fig spirit distilled by Yiannis just up the lane.

Things to do

Snorkel the neon-blue water at Pontamos Cove

Climb to the Knights' Castle on the ridge

Eat pougia sun-dried octopus at Taverna Giorgos

Taste souma fig spirit from Yiannis

Mooring tip

Emporio quay is your berth, stern-to for around €20–30 and sheltered from the north. Space is limited on this small island, so if you'd sooner swim, anchor on sand off Pontamos in four to six metres.

Rhodes
11
Day 11

Chalki → Rhodes

The scenery changes gear at Rhodes. Thirty-two miles east brings you to Mandraki, the marina right under the medieval city, and it's worth breaking the passage with a swim at Anthony Quinn Bay just to the south, where the pines run down to the water. The old town itself is the largest inhabited medieval town in Europe, a UNESCO-listed maze inside massive walls. Walk the Street of the Knights up to the Palace of the Grand Master, then let yourself get lost in the back lanes. When the day-trippers thin out in the evening, the courtyards come into their own; the tucked-away garden bar at Socratous is a good place to end up. After a week of near-empty islands, the buzz of a real city is a jolt, though a welcome one for most crews.

Things to do

Walk the Street of the Knights

Tour the Palace of the Grand Master

Swim at pine-fringed Anthony Quinn Bay

Find the garden bar at Socratous

Mooring tip

Mandraki Marina puts you stern-to on lazy lines for €60–90, right under the walls. Top up the fuel at the entrance berth before you moor, and reckon on the marina being busy in high summer.

Symi
12
Day 12

Rhodes → Symi

Symi is the showstopper of the Dodecanese, and it knows it. The harbour at Gialos climbs the hillsides in tiers of ochre, peach and faded blue mansions, most of them built on the wealth of the old sponge trade. Getting a berth is the catch: the inner quay is small and fills fast, so in peak season we push to arrive by four in the afternoon, or take the easy anchoring option in Pedi Bay a couple of miles east instead. Once you're settled, the town is all steps and cats and jewellers. Buy a natural sponge straight off a harbour stall, order the sweet little Symian shrimp fried whole at a quayside taverna, and if there's time, take the tender round to Nanou for a swim you can only reach from the water. The Panormitis monastery down the coast rewards the detour.

Things to do

Buy a natural sponge from a harbour stall

Eat whole-fried Symian shrimp at the quay

Tender to Nanou Beach for a swim

Visit the 18th-century Panormitis Monastery

Mooring tip

The inner quay is stern-to for €30–50 but tight, and it's usually full by around four in the afternoon in season, so arrive early. If it's gone, anchor on sand in Pedi Bay two miles east in five to seven metres.

Kos
13
Day 13

Symi → Kos

The last real sailing day is a long one, thirty-eight miles northwest on what's usually a comfortable beam reach back to Kos. Kos Marina is the biggest charter base in the Dodecanese, with full services and a fuel berth, so top up before you tie up to save hassle in the morning. The town rewards a final wander: the ancient healing sanctuary of the Asklepion sits on the hillside above, and Therma Beach to the east has a natural hot spring that runs straight into the sea. For the farewell dinner, the square at Platia Platanou is the place, where you eat kleftiko, slow-cooked lamb, beneath a plane tree said to be around two and a half thousand years old. Give the boat a clean tonight; it makes the handover tomorrow far quicker.

Things to do

Walk the ancient Asklepion healing sanctuary

Swim the hot spring at Therma Beach

Eat kleftiko lamb on Platia Platanou

Refuel and clean the boat at the marina

Mooring tip

Kos Marina is stern-to on lazy lines for €60–90, with a fuel berth at the entrance to fill before you moor. Confirm your handover slot with the base a day ahead so the morning runs smoothly.

Kos
14
Day 14

Kos → Check-out

Disembarkation days tend to feel a little flat, but Kos makes the ending easy. The base wants the boat back before nine, so it pays to have bags packed and the deck tidy the night before. The handover itself is straightforward: you walk the boat with the base manager, they check her over, and the security deposit is normally released within seven days once everything is signed off. If your flight is later in the day, there's time for one last swim; Tigaki, a long shallow sand beach on the north coast, is the easy choice, or you can linger over a frappé at a café in Kos town and watch the next crews arrive. The airport is only about twenty-five minutes away by road, so there's no need to rush the last coffee. Two weeks and a full circle of the Dodecanese behind you.

Things to do

Walk the boat with the base manager

Take a last swim at Tigaki Beach

Have a frappé in Kos town

Transfer to Kos airport, 25 minutes away

Mooring tip

Hand the boat back at Kos Marina before nine, then let the base run the inspection. The deposit usually clears within seven days once the checklist is signed off.

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