An example week · Cyclades · 7 days · Round trip from Athens
Cyclades Sailing Trip from Athens
Kea, Serifos and Milos on your own private yacht: white villages, volcanic sea caves and the bluest water in Greece. This is an example week. Yours starts from it and follows your group.
Duration
7 days
Start & finish
Athens
Sailing level
All levels, with a skipper
Price
On request
Why the Cyclades
The Greece of the postcards, reached by sea
White villages above the harbours, volcanic coastlines and deep blue water. Sailing is the best way to see the Cyclades: you reach the bays no ferry stops at and swim where only a boat can go.
The Aegean here is livelier than the Saronic, especially when the summer meltemi blows. That's why I plan the route, the yacht and the skipper around the season and your group, so every passage stays comfortable.
The route · 4 waypoints · ~195 nm
Your route, stop by stop
Four waypoints across seven days, so there's always time to slow down. Fall in love with Milos? Stay another night. The route follows you and the wind, not the other way round.
STOP 01
Athens → Kea
An easy first sail southeast to Kea, the first island of the Cyclades, and a calm anchorage for your first night.
Hilltop Chora · The ancient Lion of Kea · Koundouros bay · Snorkelling over reefs and wrecks
STOP 02
Kea → Serifos
Deeper into the Cyclades to Serifos, where the white Chora sits high above the port and golden bays wait below the cliffs.
Chora and the Venetian castle · Psili Ammos beach · Trails between villages · Chickpea fritters and caper salad
STOP 03
Serifos → Milos
South to volcanic Milos: sea caves, colourful fishing villages and the clearest water of the trip.
Swim through the arches of Kleftiko · Sarakiniko's white lunar rocks · The ancient theatre · Sunset over Plaka and Klima
STOP 04
Milos → Athens, two ways home
Return via Kea's Kavia bay (55 + 40 nm) for a last quiet night under the stars, or via Agia Marina on Aegina (75 + 15 nm). We choose together, with the wind on the day.
Last night at anchor · A final swim · Easy last leg into Athens
Want more? Add a stop
Alternatives we can add along the way, if you feel like it.
+ Optional
Sifnos
Whitewashed lanes, pottery villages and some of the best cooking in the Cyclades.
+ Optional
Syros
Ermoupoli's neoclassical waterfront, the elegant capital of the Cyclades.
More than a boat
I take care of everything, A to Z
I'm not a yacht owner or a booking platform. I plan your whole trip personally and coordinate everyone on the ground, so you just show up and enjoy it.
01
The right yacht
Sailboat, catamaran or motor yacht, chosen for your group, your budget and the Aegean winds.
02
Skipper & route
A trusted local skipper and a route built on season, weather and your pace.
03
Provisioning
Food and drinks on board before you arrive, dietary needs included.
04
Transfers
From the airport or your hotel to the marina, and back again.
05
Activities & local tips
Diving, hikes, and the tavernas only locals know.
06
A clear estimate
An indicative price that depends on the boat, the season and what you want included. You see it before you commit.
How it works
Personal from the very first conversation
No booking engine, no templates. Before I plan anything, we talk it through by email, so the trip is really yours.
You reach out
Send the short form or an email with your dates and who's coming.
We talk it through by email
You tell me what you dream of, how you like to travel and what matters most to your group.
I design your trip
Yacht options and a route built around you and the season.
You confirm, I handle the rest
I coordinate the yacht, skipper, transfers and extras, and stay with you during the trip.
Cyclades Sailing Gallery
The Cyclades in pictures
What guests say
More like a friend than a travel agency
“Excellent service from start to finish. Vaggelis took care of all the details and helped us organize a wonderful sailing trip in the Cyclades. Great communication and very professional.”
Ilias Marinis · Greece
“It was our first time sailing in Greece and we were a bit lost in the beginning. Vaggelis really listened to what we wanted and helped us plan a route that felt perfect for us. The boat, the little villages, the food, everything felt easy and personal.”
Katerina Liapi
FAQ
Good to know
How much does this trip cost?
There is no fixed price. It depends on the yacht, the season, the size of your group and what you want included, such as skipper, provisioning or transfers. Tell me your plans and I send you an indicative estimate before you commit to anything.
When is the best time to sail the Cyclades?
June and September are ideal: warm sea, fewer crowds and gentler winds. July and August are high season, with stronger meltemi days that I plan around with shorter legs and sheltered bays.
Is it suitable for first-time sailors?
Yes, with a skipper. The Cyclades have longer passages and livelier seas than the Saronic, so I adapt the daily distances to your group and choose calm, protected anchorages. If you want the gentlest first trip, the Saronic is the easier choice.
Can I change the route or add stops?
Of course. The stops are a suggestion, not a schedule. Stay longer where you love it, skip what you don't, and adapt to the wind on the day.
Can children join?
Yes. Many families sail this route. I shorten the daily legs, plan around the weather and choose safe, family-friendly bays.
Ready to set sail?
Let's plan your Cyclades sailing trip together
Tell me your dates and who's coming, and we'll shape the trip together by email. Personal, and with no obligation to book.