SailboatKos
Sailboat JUET 37 11.00
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Illustrative photograph: Patmos · Robert Koorenny / Unsplash
Approximate destination locations for trip planning. Use current nautical charts and local information for navigation.
Kos · Nisyros · Tilos · Halki · Rhodes · Symi · Panormitis · Kalymnos, Pothia · Leros, Lakki · Patmos · Arki · Lipsi · Kalymnos, Vathy · Pserimos
By Brieg · Updated 20 October 2026
Two weeks to sail the whole Dodecanese from Kos: south past the Nisyros volcano, Tilos and Halki to Rhodes and Symi, then back north through Kalymnos, Leros, Patmos and Lipsi. It is the only way to see both faces of the archipelago without a one-way charter: the knights' city and neoclassical waterfronts in the south, monasteries and quiet islets in the north. Around 265 miles, with one key leg to sail upwind. Details below.
The itinerary at a glance
| Parameter | Detail |
|---|---|
| Departure base | Kos (Kos Marina) |
| Access | Flight to Kos (KGS), marina 25 min away |
| Total distance | ~265 NM |
| Sailing time | ~53 h over 14 days |
| Duration | 14 days / 13 nights |
| Level | Intermediate to experienced (Meltemi, upwind leg from Symi to Kos) |
| Recommended boat | 40-46 ft monohull or 40-45 ft catamaran |
| Best period | Late May to June, September |
| Winds | Meltemi from NW to W, 15-25 kt in July-August, gusts in the lee of high islands |
| Indicative budget | ~€1,400 to €2,400 per person for two weeks (see Greece sailing budget) |
| Month | Meltemi | Air | Sea | Note |
|---|---|---|---|---|
| May | Light to moderate | 24-26° | 19-20° | Cool water, quiet islands |
| June | Moderate | 28-30° | 22-23° | Ideal |
| July | Strong (20-25 kt) | 31-33° | 24-25° | Experienced crews |
| August | Strong, gusty | 31-33° | 25-26° | Weather margin essential |
| September | Easing | 28-30° | 24-25° | Ideal |
| October | Variable, first southerlies | 24-26° | 22-23° | End of season |
| Day | Leg | NM | Mooring | Shelter |
|---|---|---|---|---|
| D1 | Kos to Nisyros | 16 | Pali harbour | Good |
| D2 | Nisyros to Tilos | 20 | Livadia | Good |
| D3 | Tilos to Halki | 18 | Emborio harbour | Good |
| D4 | Halki to Rhodes | 38 | Mandraki / Rhodes marina | Good |
| D5 | Rhodes, day ashore | 0 | same | n/a |
| D6 | Rhodes to Symi | 22 | Gialos | Fair |
| D7 | Symi, Gialos to Panormitis | 10 | Panormitis bay | Very good |
| D8 | Panormitis to Kos | 40 | Kos Marina | Good |
| D9 | Kos to Kalymnos | 12 | Pothia | Fair |
| D10 | Kalymnos to Leros | 17 | Lakki | Very good |
| D11 | Leros to Patmos | 20 | Skala / Grikos | Good |
| D12 | Patmos to Lipsi via Marathi and Arki | 15 | Lipsi harbour | Good |
| D13 | Lipsi to Kalymnos | 24 | Vathy fjord (Rina) | Very good |
| D14 | Kalymnos to Pserimos to Kos | 14 | Kos Marina | n/a |
| Total | ~265 |

Photo: Nisyros · Nicolas Lysandrou / Unsplash
Nisyros, the Dodecanese volcano: from Pali, head up to the Stefanos crater, then explore Mandraki and its lanes below the Spiliani monastery.
Tilos and Halki, two tiny, almost car-free islands that set the slow pace of the southern archipelago.
Rhodes, the medieval city of the knights, a UNESCO World Heritage site, explored on foot from Mandraki. The day ashore is well spent.

Photo: Symi · Dimitris Kiriakakis / Unsplash
Symi, the neoclassical amphitheatre of Gialos, then the enclosed bay of Panormitis and its monastery, one of the best-sheltered moorings of the loop.

Photo: Leros · August Politis / Unsplash
Leros, the Lakki roadstead and its 1930s Italian rationalist architecture, one of the safest natural harbours in the eastern Aegean.
Patmos, the Monastery of Saint John and the Cave of the Apocalypse above Chora, the second UNESCO site on the route.
Marathi, Arki and Lipsi, the quiet Dodecanese: fishermen's tavernas, turquoise water, one anchorage per islet. Full details in our 7-day northern Dodecanese itinerary.
Vathy fjord on Kalymnos, a narrow rocky inlet opening onto a valley of mandarin groves.
See also: the guide Sailing the Dodecanese, the 7-day itinerary from Rhodes to Kos and How much does a sailing week in Greece cost.
Nautical data: distances estimated on direct routes between harbours, local port authorities. Weather: HNMS. Moorings and navigation rules near Turkish waters to be checked with the charter base and an up-to-date pilot guide.
Page type: Itinerary (schema.org TouristTrip).
Logbook. Two weeks in the Dodecanese means no longer choosing between Rhodes and Patmos. The southern week is sailed downwind, the northern week in the shelter of the big islands: this archipelago suits a loop better than the Cyclades.
The mistake to avoid. Sailing the loop the other way round. Heading north first leaves the upwind leg from Symi for the last two days, with no margin if the Meltemi picks up.
Our favourite, and what we skip. Favourite: Panormitis bay at sunset, and Arki. Skip: Kos town in the middle of August; one evening at the start is enough.
Our verdict. Beauty 5/5. Anchorages 4/5. Ease 3/5. Crowds 4/5. Verdict: the most varied loop in eastern Greece, as long as you respect the direction of travel.
Yes, with a crew comfortable upwind and a real weather margin for the Panormitis to Kos leg. Late May, June and September are calmer.
Yes, from Kos to Rhodes or the reverse, which removes the upwind leg. Allow for the operator's one-way fee and a return flight from Rhodes (RHO).
Monohull for the upwind leg back to Kos; catamaran for comfort at anchor and shallow draft at Arki or Pserimos, provided you split the D8 leg.
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