September 2026

12-Day Sailing Holiday Dodecanese & Cyclades Islands, Greece

For the first time ever, we’re sailing out from our winter base in Leros, plotting a westward course through the Cyclades — the kind of route that makes your sunscreen work overtime — before wrapping up in Kos with a cold beer and a good story or two. This isn’t your usual loop-around-the-islands kind of trip. It’s one-way, a little wilder, and packed with new favourites: from quiet Levitha and dramatic Amorgos to the show-offs Paros, Ios, and Santorini herself. Expect longer sails, steady winds, and the kind of “how is this my life?” moments that SeaScape trips are made of.

Islands of Leros, Levitha, Amorgos, Donoussa, Paros, Ios, Santorini, Astypalia, Nisyros, Turkey (Datca peninsula), Kos*
Departure: Leros Marina
Return: Kos Town
Check In - Friday 9:00 AM
Check Out - Tuesday 9:00 AM

We start from our winter home base on Leros, then head west — swapping the Dodecanese for the wild beauty of the Cyclades. Expect a mix of quiet gems and showstoppers: Levitha for total peace ; Amorgos with its clifftop monastery and those Big Blue vibes; and Donousa, so untouched you’ll swear we discovered it by accident. From there, we sail on to the headline acts — Paros, Ios, and of course Santorini, where we’ll stay two nights so you can wander the whitewashed alleys, sip local wine, and watch the sunset with everyone else pretending they’re in a movie. After Santorini, we turn east again toward Astypalea, Nisyros, and the Turkish Datça peninsula — still wonderfully off the radar, with clear bays, friendly tavernas, and the kind of sunsets that make you want to stay forever — before finishing the trip in Kos, a little windswept, well-fed, and happily sun-dazed.

* 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.

Dodecanese - Cyclades sailing holiday for solo travelers

This sailing itinerary is currently only available as share boat week. Traveling solo, with your partner or a friend? Hop on board of one of the ‘share boat‘ weeks together with other fellow travellers.

share boat - 12 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)*

€ 2195

low season

€ 2495

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

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!).

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 – Leros to Levitha

Embark 9:00 AM in Leros, our home base during winter. After boat briefing, unpacking, and generally getting comfortable with the yacht, we’ll set sail for Levitha. On this first day, we immediately start with a good day of sailing. We’ll have lunch on the go as there are no others islands between Leros and our destination, Levitha — a tiny island run by one family and one excellent taverna. After arriving, we’ll open the fridge for the first ‘anchor beers’ of this trip.

Miles: 21
Duration: 4.5 hours

Levitha to Amorgos

After breakfast, we point west toward Amorgos, with its rugged cliffs. En route we stop in a quiet bay for lunch and a swim, before continuing our journey towards the island made famous by The Big Blue. The Panagia Hozoviotissa monastery clinging to the rock is worth the climb.

Miles: 28
Duration: 6 hours

Amorgos to Donoussa

A true off-the-beaten-track gem — Donoussa has a few tavernas, a few locals, and peace so deep you can hear the sea breathe.

Miles: 15
Duration: 3 hours

Donoussa to Paros

We sail along Naxos where we stop for lunch, continuing our journey to Paros, where the whitewashed lanes and lively harbour cafés are made for wandering. It’s a lively change of pace — time for a cocktail or two before dinner in one of the island’s waterfront tavernas.

Miles: 33
Duration: 7 hours

Paros to Ios

With the Meltemi in our back, today’s the day for a relaxing downwind sail to Ios. Ios is all golden beaches and friendly tavernas — lively in spots, peaceful in others. We’ll find a good one for dinner and maybe some live music ashore.

Miles: 33
Duration: 7 hours

Ios to Santorini

There’s nothing quite like a downwind sail from Ios into Santorini’s volcanic caldera — cliffs rising around us, sunlight dancing on the water. We’ll stay two nights, giving time to explore Oia and Fira, taste the island’s wine, and enjoy a sunset or two you won’t forget.

Miles: 18
Duration: 4 hours

Santorini

A bonus day on Greece’s most photographed island. Hire a car and go explore the island!

Santorini to Astypalia

We wave beautiful Santorini goodbye and start sailing back towards the East, heading to the butterfly-shaped island of Astypalia. Wander to the castle-topped Chora — quiet, authentic, and one of Greece’s prettiest villages.

Miles: 53
Duration: 11 hours

Astypalia to Nisyros

A full day’s sail with lunch on the go until we reach Nisyros, another volcanic beauty. Get up early in the morning to drive up to the volcano crater for a walk through history. Part of Moonraker was filmed here.

Miles: 41
Duration: 8.5 hours

Nisyros to the Datça peninsula

We make a pit stop into Turkey, where we like to visit Ogun’s Place — where Ogun himself welcomes you with his heartwarming smile before he shows you the delicious meze that are on the menu that day. With fresh bread coming straight out of the oven, this is a feast for the tastebuds.

Miles: 19.5
Duration: 4 hours

Datça peninsula to Kos

Our final sail brings us back into Greek waters and into Kos, where we start our summer sailing trips. One last opportunity for a few laughs at sea, and a celebratory final dinner ashore — the perfect ending to a true Aegean adventure.

Miles: 27
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!

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?