Sailing in Greece

Our Original Island Adventures

Our yacht charters and sailing adventures in Greece first started in the Dodecanese islands, way back 25 years ago. Even then, one had to travel a bit further afield to find the “real Greece”. Quarter of a century and thousands more tourists later – that’s even more true now. Of course, if your vacation goal involves drinking in Irish bars and eating McDonalds – head for the “big name” islands. Or start your sailing trip from Athens, and fight tooth n’ nail for dock space in the nearby islands.

But you’d prefer to experience some of the old-style Greek ambiance, with all it’s original colour and lively spirit, we are just a 50 min plane ride away from Athens.

We think it’s worth it.


This is an example of a typical itinerary on one of our 1 week sailing trips around the Dodecanese islands. Please bear in mind that no two trips are ever exactly the same; only the start and end points are fixed. Otherwise, we go with the flow of what Poseidon dictates, and the preferences of those on board!

One week sailing in Greece

fishing boat in Lipsos, Greece

Day One - Embark 11am in Lakki (main harbour on Leros). After boat briefing, unpacking, and generally getting comfortable with the yacht, we'll set sail for Lipsos - island of the 42 blue-domed churches. It is the perfect introduction to "traditional Greece"; a small, untouristy village, with an unruly array of whitewashed buildings scattered around the bay. The vivid streaks of traditional blue trim and the blazing bougainvillea pinks & purples make it a real photographers' dream!

To cool off, there is a lovely little sandy beach, 5mins walk over the hill from where we moor the boats, and a great hike out to the headland with spectacular views out to sea.

If conditions are calm, we may be able to visit Macro Nisi for a swim stop en route. It's a secluded little anchorage with sheer-sided cliffs, which have been known to entice the braver (or more foolhardy!) amongst us to throw caution to the wind and leap off them ! For those more inclined to be adventurous in the water, there's a very cool, semi-submerged tunnel through the cliffs through which one can snorkel, emerging in little cave on the other side of the island.

sailing boats in Marathi, Greece

Day Two - Early morning sail to Marathi - a truly tiny little island with a sandy, horseshoe-shaped beach, beautiful water to swim and snorkel in; a totally tranquil and peaceful spot. If you could paint a picture of the perfect, idyllic island retreat, Marathi would be it. There are just two families living here; wonderfully friendly and hospitable people. The food is incredible too !! This place is a magical balm for the stressed-out city-living much so that it's often been hard to persuade people that, really, we should leave, there are other islands to visit ! Sail time, approx 3hrs.

Patmos - view from the monastery

Day Three - Sail to Patmos - an early start to make the most of exploring the famous Monastery Island, where St John was inspired by visions to write the Book of Revelations. The 10th century monastery (built by Crusader Knights) reigns over the island, still an active and influential part of daily life here. The village that lies at the foot of the monastery is everyone's romantic image of a Greek village; narrow winding alleyways scarcely wide enough for a skinny donkey! - cats sunning themselves on whitewashed streets, old ladies in black collecting fresh bread from the bakery in the morning.

It's well worth an early rise to get up there in the dawn hours; the old ladies will look at you in faint amazement that a foreigner should find their way up there at such a time; if you can remember enough of our Greek lessons to say "kalimera!" (good morning), they'll give you a huge smile and a "kalimera-sas" back (good morning to you too) ! (Note: that's "kali-MER-a", not "calamari" :> ).

sailing boats in Pandeli, Leros - Greece

Day Four - Sail for Pandeli , a beautiful little bay on the east side of Leros. This is one of the prettiest anchorages to sail into you can imagine; a horseshoe-shaped bay with traditional blue-and-white houses scattered down the hillside. An 11th century fortress towers over the bay, and our favourite little beach tavernas are just 2 mins swim from the boat. Try sitting and watching the moon rise from one of these tavernas, boat in the foreground, the lapping of waves almost at your feet - it's a total "Shirley Valentine" scene !

For those with more energy to burn off later, there is the infamous Savana Bar a very idiosyncratic little local hangout, where we often end up dancing the night away till the wee small hours! Another great island to rent scooters and explore.

sailing boats docked in Vathi, Kalymnos ,Greece

Day Five - A leisurely morning in Pandeli; time to hike up to the fortress and get some stunning panoramic shots from the island's highest vantage point; or perhaps just a cooling swim from boat to taverna, to recover from that dangerous Savana Bar place!

Around midday, we'll set off for Vathi ; a relaxing downwind sail of about 3hrs.

Vathi is a dramatic little spot; a well-hidden and very narrow fjord-like entrance, opening up into a tiny fishing village at the head of the bay. It boasts one main street and a collection of houses scattered into the valley; an unexpected patch of lush vegetation on an otherwise very dry and arid-looking island. Vathi is the only place on the entire island that is lucky enough to have it's own spring water supply, and they use it carefully to cultivate citrus fruits, figs, grapes and anything else that can be persuaded to grow.

sailing boats anchored in Paleonissos, Kalymnos

Day Six - Sail to our lunch-n-swim stop at one of the little, uncrowded bays around Kalymnos. Time to go hike around the hills and maybe pick some beautifully scented sage to make a fine, healthy brew of sage-and-local-honey tea!

After lunch, it will be time to sail back to Lakki and our marina base. The luxury of land showers and a laundry, and perhaps a cold one at "Skipper's Bar". Our final dinner is usually at a gorgeous beachfront restaurant, where the owner often treats us to some amazing bouzouki music (He is the islands' music teacher, and his sons are equally gifted!).

the village Hora in Patmos

Day Seven - Disembarkation is at 9am. For those wishing to stay longer in Leros, we can recommend some great little places to stay around the island. For onward travel, there are 2 flights per day back to Athens. Please note, if you would like to get the early morning flight on Sat from Leros-Athens, it is entirely possible; the airport is just 15 mins from our dock, and we can organise taxis easily.

For other onward travel - the Blue Star ferry runs a couple of times a week to Athens. The fast catamaran runs everyday up and down the Dodecanese chain.

Sailing in Greece – Local Info

“Dodecanese” means Twelve Islands – though we’ve counted a few more than that! It’s a great variety of ideally-spaced anchorages for the cruising sailor – around 3-5 hrs sailing time between islands.

There are a couple of well-known, lively spots which we sometimes throw into our itinerary mix – after all, it wouldn’t be Greece without a little party spirit! But we’re mostly about experiencing the traditional, blue-and-white villages, exploring 12th century fortresses, or sharing a retsina with the locals in tiny fishing harbours.

For those who like a little adrenaline with their sailing – the midsummer months have the strongest winds – 25knots or so on average.  It tends to be a little mellower in the early and late season.  From late May-Oct, it’s pretty much guaranteed sun, sun and more sun – once again, a perfect yachties’ playground!

For lots more info about our sailing adventures in Greece, check out our FAQ page