12-day Cyclades Route, Greece

A new SeaScape adventure from Leros via showstopper Santorini, returning to Kos — visiting Levitha, Amorgos, Donoussa, Paros, Ios, Astypalea, Nisyros, and the Turkish Datça peninsula.

This one’s an Aegean dream for sailors, heading West after departure from Leros – our winter home – to explore the off-the-beaten-track islands of the Cyclades. This trip ends in Kos.

Along the way, we’ll island-hop through some of the most beautiful (and least crowded) corners of the Aegean until we reach Santorini, the crown jewel of the Cyclades. Expect steady Meltemi winds as we head west, and a few longer sailing days compared to our 7-day northern or southern routes — making this voyage ideal for those who love a dose of adventure.

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.

See full screen

Sample itinerary

Day 1 - Leros Marina 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

Day 2 - 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  

Day 3- 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  

Day 4 - Donousa 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 hour

Day 5 - 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

Day 6- 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

Day 7 - Santorini

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

Day 8 - 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

Day 9 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

Day 10 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

Day 11 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

Day 12 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!

Best time to sail

May – October are the best months to sail along the Greek islands.

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!

Schedule for the 12-day Cyclades sailing route

View the schedule here (Shareboat trips are usually planned upfront in this schedule, while the remaining ‘open’ weeks are available for private charters along any desired route.)

12-day Cyclades route sailing options

Shareboat

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

12 days € 2495 per person (shared cabin)
+50% supplement for single use cabin

About Shareboat

 

Ready to hop on board?