On the Water
Greek Islands under Sail
Cyclades, Dodecanese, Ionian Sea
Bays reached only from the water — and harbours that empty in the evening.
You know the Cyclades from photographs: Paros, Milos, Folegandros, Amorgos. From a boat they look different, because you swim at dawn where the day trippers moor at noon, and anchor once the last ferry has gone.
A sailing yacht with four to six cabins and its own crew is the right size: small enough for small harbours, steady enough when the meltemi blows. Breakfast aboard, dinner often ashore, in tavernas the crew actually knows.
The Ionian is the alternative for families: shorter legs, green islands, calmer water — Ithaca, Kefalonia, Paxos.
The Pure Voyage view
Why we recommend it
Because a yacht in the Aegean spares you the ports, not the islands.
The gain is not the boat but the bays: swimming where no ferry goes and mooring in the evening where you want to eat. Seven nights is the minimum, otherwise the trip becomes a transfer. We plan the route around the meltemi rather than around a wish list — in July and August the wind decides which Cyclades are possible. June and September are calmer and more pleasant.
- Who it suits
- Families and groups of friends travelling together
- What stays
- A morning bay with no second boat in it
Suitability
Who it is for
Ideal for
- Families and groups of friends
- Travellers linking several islands without ferries
- Seven to ten nights
- June and September
Less suited for
- Guests who want a lot of time ashore
- Travellers prone to seasickness in the meltemi
- Very short charters
What travellers often underestimate
The meltemi in July and August sets the route. A flexible plan is worth more here than a fixed island list.
If this is not the right fit
You may also want to consider
If Greece stays but the yacht does not:
01 · Paros
Parīlio
One island as a base, with day trips rather than daily moves.
02 · Folegandros
Gundari
Very quiet and remote, for couples who need no programme.
03 · Dalmatien
Kroatien per Yacht
Shorter legs, more sheltered water, less wind in high summer.
Not better, not a step up — simply different, and right for different travellers.
Our view
Why we recommend it
Because from the water Greece becomes again the country it was before mass tourism. And because a week aboard removes the island-hopping logistics that otherwise eat half the holiday.
- Best time to travel
- May, June and September. July and August bring meltemi and full harbours; early October is warm and very quiet.
- Suggested duration
- Seven to ten nights aboard, with three nights on an island before or after.
- Who it is best for
- Families, groups of friends, couples who want to be close to the water. Less so if you need a proper bathroom and space every evening.
Pure Voyage note
Do not fix the route in advance. The meltemi decides anyway — the best weeks are the ones where the skipper asks each morning where to go.
Along the way
Retreats along the way
The addresses we suggest most often for this journey — as a starting point, not a fixed route.
Parīlio
Paros
Two nights ashore before casting off — calm and full of light.
Gundari
Folegandros
On the cliff, to close the sailing week.
Amanzoe
Peloponnese
For when the mainland should belong to it too.
And then
Journeys that sit well beside it
Antarctica Expedition
The only place where silence has a size.
Tuscany from Place to Place
Short drives, long lunches — the landscape sets the timetable.
Galápagos by Private Yacht
Sixteen guests rather than a hundred — the same islands, an entirely different experience.
Whether this journey suits you is settled fastest in conversation.
Season, length and the hotels before and after shape the result more than the route ever does.
Speak with the conciergeWhat should shape the timing?
The meltemi. In July and August it blows hard across the Cyclades, shortening routes and closing anchorages. Early June and September are calmer, the sea warmer and the harbours quieter. Seven nights suits four islands — more stops mainly means more time under way and less at anchor.
Noted by Pure Voyage
Common questions
What guests ask us about this
- Private yacht or small ship?
- A yacht gives you freedom over route and rhythm; a small ship removes the organising and the cost. From roughly eight people the yacht starts to make financial sense too.
- How far ahead should you book?
- Six to twelve months for the Mediterranean summer. Good crews and the sought-after weeks in July and September go first.
Pure Voyage Signatures
Themes that run through our work
Recurring thoughts rather than categories. They appear where they explain something.
You may also enjoy
Where else we would send you
Not the most similar, but the most natural next step: places, routes and essays that belong to this way of travelling.
- HouseAmanzoePorto Heli, PeloponnesA house we would mention in the same conversation.
- DestinationGreeceIslands that look alike — until you stay three days.The country behind it — how everything connects.
- RecommendationGreece We LoveThe Greek islands we return to ourselves.Our selection for travellers with this outlook.
- JournalWhere to Travel in October6 minutesAn essay that carries this thought further.
Continue through Pure Voyage
Where to go from here
Not a catalogue, but a next step: the retreats, routes, countries and essays we would mention at this point in a conversation.
Hotels
Addresses that belong beside this page.
Destinations
The country at a glance.
Recommendations
What we suggest for this occasion.
Journal
Further reading before you decide.
Further reading
What we have written on this
Insider Recommendations
Houses With a View That Stays
A good view is rarely an accident. Six addresses where the outlook is the real room.
Destinations
Which Greek Island Suits You?
Cyclades, Ionian, Crete: the differences are larger than the postcards suggest.
Guest Voices
What stays with you
Not stars or ratings — but what you remember afterwards.
We had two retreats in mind and booked a third in the end. The reasoning was so clear that the decision became easy.
M. K. — HamburgAmalfi Coast, May The advice on which weeks to avoid changed our journey. We went two weeks later — and had the river to ourselves.
Dr. A. S. — MünchenTanzania, family journey
Published with consent, shortened and anonymised.
A Personal Enquiry
Shall we plan Greek Islands under Sail for you?
Tell us when you would like to travel and with whom — we check availability, cabins or rooms and the right opening to the trip.
A first assessment is without obligation and free of charge.
Why book through Pure Voyage?
- Personal luxury travel advice
- Carefully chosen hotel recommendations
- Tailor-made itineraries
- Partner benefits wherever they apply
- Direct personal contact from start to finish
An Invitation
Once a month: hotels, new openings and travel ideas
One hotel that convinced us. One new opening we are watching. And one travel idea for the right season. Carefully selected and reduced to the essentials.