Embark 9:00 AM in Lakki Marina, 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

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

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

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

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

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

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

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

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

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

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