YachtSailingYachtSailing

Places to explore · not a fixed schedule

Where a Cyclades charter could take you

The famous islands and the quiet ones in between - explore the map, then shape your own days with your captain once you're aboard.

What you'll see below

Places to explore, not a schedule

There's no fixed itinerary here - just the islands and hidden spots guests love most, mapped out so you can picture where a Cyclades charter could take you. Two routes below, tap between them; tap the map to explore, then shape the real order with your captain once you're aboard, around the wind and what you feel like.

OUR GUESTS' FAVOURITE CYCLADES ISLANDS for 2026 Intensity

Cyclades Islands

Typically 7 days

Tap any place — on the map or in the list — for a closer look. Sail times shown are indicative only.

Useful hints

Size plays a role in how fast you go and the sense of stability you get - regardless of the space inside, and regardless of where you're sailing.

  • ●Larger catamarans have a longer waterline, allowing them a higher potential cruising speed - covering distances in a shorter period of time.
  • ●They also sit higher above the water, which many guests find gives a steadier ride - a better sense of stability.
Islands you might visit

Every stop worth knowing about

E

A note from Eugene

The Cyclades: Where Experience Matters

— Eugene, YachtSailing
Who you're sailing with

Why crew experience matters

Since there's no fixed itinerary, it's your captain and hostess who shape each day - reading the wind, adjusting the route, deciding where to stop next. That's exactly why it matters who you're sailing with.

25+ Years Cruising the Greek Islands

Permanent, Long-Standing Crews

Background Checked Professionals

First Aid & Safety Trained

Deep Local Knowledge of Every Anchorage

A yacht, an area

Sail the Cyclades aboard Queen of Diamonds

A 52ft catamaran for up to 10 guests - a calm, elegant choice for the Cyclades' longer passages and famous islands.

Queen of Diamonds
The Cyclades
The Cyclades
Good to know

Questions about planning your charter

Is this an itinerary we are expected to follow?

Not at all. The routes shown here are designed to give you a realistic idea of where a week in the Cyclades could take you, rather than a schedule we expect you to follow.

Before your arrival, we discuss the places you would particularly like to see, how much sailing your group enjoys and what you want from the week. Once onboard, your captain brings those preferences together with the weather conditions to shape the actual route.

Think of these routes as inspiration and a sense of distance — not a timetable.

Which of the two Cyclades routes should we choose?

The first route brings together some of the more iconic Cycladic names, including Mykonos and Paros, alongside islands such as Kea, Syros, Serifos and Kythnos. The second heads south towards Sifnos, Milos, Kimolos and Polyaigos, with a stronger emphasis on dramatic coastlines, beautiful water and some quieter places away from the better-known islands.

There is no better route. The choice depends on what interests your group, how much sailing you enjoy and, ultimately, the conditions during your week.

And you do not actually need to choose between them before arriving. Islands from either route can be combined when distances and weather make sense.

How much sailing should we realistically expect?

The Cyclades involve longer distances and more open-water sailing than the Saronic. Some passages may be relatively short, while others — particularly the first or final crossing from Athens — can be considerably longer.

But we don't build the week around accumulating sailing hours. There needs to be time to swim, explore a village, discover some history, enjoy the food, spend an afternoon in a beautiful bay or simply do nothing.

The best itinerary is the one that finds the right balance between travelling through the Cyclades and actually experiencing them.

How many of these islands should we try to visit?

There is no ideal number, and we would not start the week with a target.

Four or five islands properly experienced can make a far better holiday than six or seven reached simply to tick them off a list. An island might deserve an afternoon, a full day or an extra night because your group simply doesn't want to leave.

The advantage of a private yacht is precisely that the week can develop as you go.

Can we change islands or combine stops from the two routes?

Absolutely. The routes are not packages.

If there is an island you particularly want to see, tell us. Equally, if you discover during the week that you prefer quieter islands, longer swimming stops, more time ashore or less sailing, the route can evolve accordingly.

The only limits are distance, weather and what remains comfortable and realistic for your group.

What happens if the wind changes our plans?

This is particularly important in the Cyclades. The Aegean can be windy, and nobody can predict months in advance exactly what conditions your particular week will bring.

Your captain may change the order of the islands, select a more protected passage, substitute one destination for another or reshape the route more substantially if necessary.

That isn't the itinerary going wrong. It is how a good Cyclades itinerary works. Your group sets the priorities, your yacht helps define what is comfortable and realistic, and the weather always has the final say.

Is it possible that we may not sail to the Cyclades?

Yes. The Cyclades are exposed to the Aegean winds, and there may be weeks when conditions make sailing there uncomfortable or simply not the right choice for your group.

This is true regardless of whether you choose to sail with us or with anyone else. You cannot go against nature. No responsible operator can guarantee months in advance that conditions will allow a particular Cyclades itinerary. If someone promises that you will definitely reach a specific island or follow a specific Cyclades route, there is an important part of the story being left out: weather always has the final say.

Chasing an ambitious itinerary despite the conditions rarely leads to a better experience. If necessary, your captain may recommend heading towards the more protected Saronic Gulf instead.

For us, it makes no difference which direction you ultimately sail. What matters is that you get the very best out of your time in Greece. The Saronic is not a lesser alternative — it is a different part of Greece, with beautiful islands, calmer waters and shorter distances, often leaving more time for swimming, exploring ashore, discovering local history and culture, enjoying the food and actually experiencing the places you visit.

We would always rather change direction and give you a great week than spend your holiday fighting the weather simply because the original plan said "Cyclades."

Your preferences help us plan the week, but weather always has the final say.

Are the sailing times shown on the map exact?

No. They are there to give you a sense of distance, not an arrival time.

Actual passage times will vary according to the yacht, wind, sea conditions and route taken. They should be used to understand the relative distance between islands rather than to plan the week hour by hour.

Ready to start planning?

Tell us who's coming and what you're after - our advisors will shape the right region, route and yacht to match.

Talk to a yacht advisor → Book a video call →
Ask an advisor

Get in touch

Contact usSend an enquiry, a real advisor replies personally Arrange a video callPick a time that works for you Call us+30 693 723 4566 WhatsApp usAlso available on the same number