June - October

7-Day Sailing Holiday Northern Dodecanese Islands, Greece

Imagine this: a taverna-lined harbor where cats lounge in the shade, ouzo flows like water, and your sailboat bobs gently just steps from the shore. This is your Greek island sailing adventure through the Northern Dodecanese, SeaScape-style. It’s a sailing holiday in Greece that trades cruise ships for quiet harbors and packed tours for slow travel. Picture sun-drenched days island-hopping from Patmos to Lipsi, Leros to Arki—swimming in hidden coves, hiking to ancient monasteries, and ending each day with grilled octopus and local wine. It’s the Aegean sailing trip you didn’t know you needed—a small group sailing experience, no crowds, no stress, and no bareboat responsibilities. Just the sea, the wind, and a fresh island to wake up to every day.

A beautiful cruising area are the northern Dodecanese islands. In true SeaScape style, we stay away from the busier “touristy” spots. We visit islands like Patmos, where St. John wrote the Book of Revelations; next-door neighbour, Lipsi, which boasts at least 52 blue-domed churches, whilst the tiny paradise-island of Marathos just next to Arkoi is home to just three families.

* Mentioned islands are indicative, as the routes we plan and the islands we visit always depend on sailing conditions dictated to us by the Greek gods Poseidon and Aeolus. As true SeaScapers we always make sure you’ll have the trip of a lifetime.

Greece sailing holidays for solo travelers & private groups

All Greece sailing holiday itineraries are available for everyone. Traveling solo, with your partner or a friend? Hop on board of one of the ‘share boat‘ weeks together with other fellow travellers. The other option is to book a private charter week for your own private group, which is available for up to 8 persons.

share boat - 7 days

For individuals, couples, or friends travelling together – join likeminded adventurers on one of our share boat weeks.

Based on sharing a bunk bed or double cabin (ensuite)*

€ 1395

low season

€ 1595

high season

private charter - 7 days

Already have your own group? Charter the whole boat with our skipper and hostess to have the time of your life with your partner, family or friends on a private sailing trip. Private charters are available from

€ 6500

low season

€ 7500

high season

Low Season – May and October
High Season – June, July, August and September

*Cabins for private use in Greece are available at a 50% extra fee

Best months to sail

For those who like a little adreline 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. Even if you never sailed before, you could join any month really. There is no such thing as beginner months or intermediate / advanced months. From late May-Oct, it’s pretty much guaranteed sun, sun and more sun – once again, a perfect yachties’ playground!

Sample Itinerary

Embark the boat – Kos to Kalymnos

Embark 9:00 AM in Kos. After boat briefing, unpacking, and generally getting comfortable with the yacht, we’ll set sail for Kalymnos. Around noon we will stop in a quiet bay for a delicious on-board lunch and a swim, before we continue our sail to Vathys. A dramatic little spot and a perfect introduction to “traditional Greece”; 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. Vathys is the only place on the entire island that is lucky enough to have its own spring water supply, and they use it carefully to cultivate citrus fruits, figs, grapes and anything else that can be persuaded to grow. In the evening, we visit our favourite family restaurant BOOTSHAUS Old Poppy’s Taverna where we’ve been going to for the past we-don’t-even-know-how-many years. The chef is a magician with food, and all you have to do is let him choose what to cook that evening.

Miles: 14.5
Duration: 3 hours

Kalymnos to Leros

After a morning swim in Vathys’ ocean swimming pool next to the dock, we’ll set sail for Leros, the former home base of SeaScape Sailing and therefore an island we call home. We go for anchor in a remote, quiet bay to give you the best sailing experience: a night on anchor with a sky full of stars to fall asleep under. We’ll prepare a barbecue on board while you enjoy some quality time on the boat or go for a few rounds on the paddle board. We might go to bed early or stay up late and enjoy some great music and a few drinks, it’s really all up to you! One thing is guaranteed: after this night, you have experienced the real deal of living off-the-beaten track on a sail boat.

Miles: 22
Duration: 4.5 hours

Leros to Lipsi

We look forward to visit Lipsi – island of the 42 blue-domed churches. It is 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, a few minutes’ walk over the hill from where we moor the boat, 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.

Miles: 7.5
Duration: 1.5 hours

Lipsi to Patmos

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”).

Miles: 10
Duration: 2 hours

Patmos to Kalymnos

We set sail towards a bay next to Emporios, where we love to spend another night on anchor. Or “Pirate Bay” just around the corner, where we anchor the boat close to shore and take the dingy to go on land. This little tranquil oasis is a little Pirates in the Greek islands getaway you won’t find when you follow the main tourist tracks. It’s like a tiny safe heaven popped up in the middle of nowhere, with its own little bar and restaurant.

Miles: 24
Duration: 5 hours

Kalymnos to Kos

Sail to our lunch-n-swim stop at one of the little, uncrowded bays around Kalymnos or Pserimos. 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 Kos. The luxury of land showers and a laundry, and perhaps a cold one at a bar. Our final dinner is usually at a gorgeous beachfront restaurant.

Miles: 26.5
Duration: 5.5 hours

Disembark the boat

Disembarkation is at 9:00 AM. For those wishing to stay longer in Kos, we can recommend some great little places to stay around the island. For onward travel, there are several daily flights to many European cities. You will definitely be heading home with a nice tan!

Sailing Schedule Greece 2026

June - October

Week	Dates	Destination	Type	Availability
20	May 15 – 21	Greece, Dodecanese	Private charter
21	May 22 – 28	Greece, Dodecanese	Private charter
22	May 29 – June 4	Greece, Dodecanese	Share boat
23	June 5 – 11	Greece, Dodecanese	Private charter	FULL
24	June 12 – 23	Greece, Dodecanese 12 days	Private charter	FULL
26	June 26 – July 2	Greece, Dodecanese	Private charter	FULL
27	July 3 – 9	Greece, Dodecanese	Private charter	FULL
28	July 10 – 16	Greece, Dodecanese	Private charter	FULL
29	July 17 – 23	Greece, Dodecanese	Private charter
30	July 24 – 30	Greece, Dodecanese	Private charter
31	July 31 – August 6	Greece, Dodecanese	Private charter
32	August 7 – 13	Greece, Dodecanese	Private charter
33	August 14 – 20	Greece, Dodecanese	Private charter	FULL
34	August 21 – 27	Greece, Dodecanese	Share boat
35	August 28 – September 3	Greece, Dodecanese	Private charter	FULL
36	September 4- 15	Greece, Cyclades 12 days	Share boat
38	September 18 – 24	Greece, Dodecanese	Private charter
39	September 25 – October 1	Greece, Dodecanese	Share boat
40	October 2 – 8	Greece, Dodecanese	Private charter
41	October 9 – 15	Greece, Dodecanese	Private charter
42	October 16 – 22	Greece, Dodecanese	Private charter	FULL

What's included with SeaScape Sailing

We don’t do ‘hidden extra fees’. Excluded are transportation from and to the boat, onshore dinners, and alcoholic drinks after the Happy Hour supply we provide you with (BYO!).

Artemis, our sailing yacht in Greece

Artemis is a modern-designed 55′ sloop, with a semi-pilothouse design which creates a very unusual – and huge! – split-level saloon. She has 4 ensuite cabins for 8 guests in total, 2 double cabins in the aft and 2 bunk bed cabins forward.

Ready to hop on board?