This is the week for a group that wants range: the quiet, almost-empty western Cyclades first, then the famous islands as the finale, without ever retracing a mile. Board in Athens, sail out the same afternoon, and disembark in Mykonos seven nights later, every single day is a new island, not a rushed stop shared with another.
The trade for that range is a one-way charter, which means a repositioning fee to get the yacht back to its base. We quote it up front so there are no surprises, and for most groups the extra cost is worth never sailing the same water twice. This is roughly 220 nautical miles across the week, with the longest legs mid-week, comfortable on a motor yacht or fast catamaran.
Your captain adjusts the order to the meltemi, Greece’s summer wind, so treat the days below as the shape of the week rather than a fixed schedule.
Day 1 – Board in Athens, First Night in Kythnos (about 38nm)
Midday: boarding at Alimos Marina
Embarkation is Saturday early afternoon at Alimos Marina, the biggest charter base in Greece and a short transfer from the airport. Meet the crew, unpack once for the whole week, since you are never coming back to this boat once you step off in Mykonos, and go through the preference sheet if you have not already.
Afternoon: out to Kythnos
You are not staying put. Most crews are casting off within the hour, past Cape Sounion and the Temple of Poseidon standing on its cliff, worth slowing down for even if you do not stop, and across to Kythnos, an island Athenians have quietly kept for themselves for generations.
Evening: Kolona
Head for Kolona: a double-sided sandbar beach connecting the island to a rocky islet, water on both sides at once, and one of the best swim stops in the western Cyclades. Sunsets here make the whole anchorage go quiet. If your group wants a harbor-village evening instead, Loutra on the northeast coast has genuine thermal springs, known since Roman times and studied in the 1830s by doctors travelling with Greece’s first king, Otto.
Broker insight
This is a west-to-east Cyclades run, so you usually have the Meltemi behind you by the back half of the week. It rewards an early start each morning.
Daniel Asmus
Owner, Charter Broker, Active CYBA Member, IYBA, ECPY
Overnight: Kolona, Kythnos, or Loutra.
Don’t Miss
- Cape Sounion from the water
- Kolona’s sandbar, water on both sides
- Cape Sounion and the Temple of Poseidon from the water
Day 2 – Kythnos to Serifos (about 25nm)
Morning: south to Serifos
South to Serifos, an island with real mythology behind it: this is where Perseus is said to have grown up, and local legend places the severed head of Medusa somewhere in the catacombs beneath the old castle above town.
Lunch: under the Chora
Lunch at anchor under Serifos’ dramatic hilltop Chora, one of the finest in the Cyclades and still barely visited, whitewashed houses climbing a rock spur with the old Venetian fortress ruins on top.
Afternoon: a real day here
With the whole day on this one island instead of rushing through, walk up to the Chora properly, or find a quiet beach on the south coast, Serifos rewards the extra time.
Evening: dinner in the Chora
Dinner up in the Chora as the light drops, the walk up is worth doing once just for the view back down to the boat.
Overnight: Livadi, Serifos.
Don’t Miss
- Serifos’ Chora and its Medusa legend
- A full day on one island, not a rushed stop
- Dinner with a view back down to the anchorage
Day 3 – Serifos to Milos (about 35nm)
Morning: to Milos
On to Milos, the route’s scenery jackpot: a volcanic island whose coastline changes color every few miles, from the white moonscape of Sarakiniko to the ochre caves of Mandrakia.
Lunch: Sarakiniko or Mandrakia
Lunch at anchor off Sarakiniko, a beach of bone-white volcanic rock that looks more like the moon than Greece, or the fishing village of Mandrakia, its boat garages built straight into the cliff.
Afternoon: Kleftiko
Take the tender out to Kleftiko‘s white rock arches and sea caves in the afternoon light, while the sea is calmest. The name means “stolen” in Greek: 18th and 19th-century pirates hid their ships inside these caves between raids on passing merchant ships, and swimming through them today it is not hard to see why.
Evening: dinner ashore
Dinner ashore in one of Milos’ harbor villages, a full day here means no rush to see it all before dark.
Overnight: Milos.
Don’t Miss
- Sarakiniko’s white moonscape
- Kleftiko’s pirate sea caves, tender access only
- Mandrakia’s cliffside boat garages
Day 4 – Milos to Folegandros, via Polyaigos (about 40nm)
Morning: Polyaigos
On the way out, a stop at Polyaigos, the largest uninhabited island in the Aegean: turquoise coves, no buildings, no crowds, and some of the clearest water in Greece.
Lunch: water toys at Polyaigos
This is the day the water toys earn their keep. Lunch at anchor, then swim, paddleboard, or just float; there is nowhere else on the route this empty.
Afternoon: crossing to Folegandros
Onward to Folegandros, one of the smallest and least developed islands in the Cyclades.
Evening: Folegandros Chora
Take the path or the bus up to the clifftop Chora for dinner, a village hanging 200 meters above the sea, one of the oldest medieval towns in the Cyclades, its three linked squares closed to cars. The 13th-century Castro at its center was built by the Venetian ruler Markos Sanoudos to protect islanders from the same pirates who used Kleftiko. For many of our clients, this is the single best evening of the route.
Overnight: Folegandros.
Don’t Miss
- Polyaigos, empty water and no buildings
- Folegandros Chora at 200 meters, one of the oldest towns in the Cyclades
- Dinner in the Castro’s old squares
Day 5 – Folegandros to Santorini, via Sikinos (about 30nm)
Morning: a gentle hop past Sikinos
A gentle morning hop past Sikinos, one of the least-visited islands in the Cyclades; stop for a swim or a quick look at its tiny port if the schedule allows.
Lunch: on the approach
Lunch underway on the approach every guest remembers: into the Santorini caldera by sea, cliffs rising three hundred meters overhead, the rim of a volcano that erupted around 1600 BC in one of the largest eruptions in recorded history.
Afternoon: Oia or Fira
Go ashore to Oia or Fira in the late afternoon, once the cruise crowds thin out.
Evening: dinner on deck, or ashore
Watch the sunset from the deck with dinner on board, which our crews will tell you beats the crowded clifftop balconies, or stay ashore if the group prefers. Overnight positioning is the captain’s call, the caldera itself is exposed.
Overnight: The Santorini caldera, or Vlychada, captain’s call on conditions.
Don’t Miss
- Sikinos, one of the quietest islands in the Cyclades
- The caldera approach by sea
- Sunset dinner on deck, away from the crowded balconies
Day 6 – Santorini to Amorgos, via Ios (about 55nm)
Morning: Nea Kameni
A morning swim at the Nea Kameni hot springs, in the middle of the caldera, or one last look at the caldera before you leave; the volcano has been dormant since the 1950s but is still active, and the water off the islets runs warm and orange-tinted.
Lunch: Ios
North with a lunch stop at Ios, either Mylopotas beach or the harbor bay, before the afternoon run east to Amorgos.
Afternoon: the wild card of the week
Amorgos is the wild card of this route: steep, dramatic, and home to the Panagia Hozoviotissa monastery, built into a sheer cliff face 300 meters above the sea. Founded in the 11th century by the Byzantine emperor Alexios I Komnenos to house an icon of the Virgin Mary that is said to have arrived on the shore below from Palestine, it is one of the oldest monasteries in Greece and still active today.
Evening: Katapola harbor
If the group has energy, the evening visit to the monastery is unforgettable; if not, Katapola harbor does a very good taverna dinner.
Overnight: Katapola, Amorgos.
Don’t Miss
- Nea Kameni’s hot springs
- Hozoviotissa Monastery, 300 meters above the sea
- Katapola harbor for dinner
Day 7 – Amorgos to Mykonos, via Paros and Delos (about 65nm)
Morning: the final push
The final push north, the longest single sail of the week, so an early departure gives the whole day at sea without eating into the Mykonos evening.
Lunch: Paros or Koufonisia
A swim and lunch off Paros or the Koufonisia channel, wherever the timing works out best, the last quiet stop of the week before the route swings into the busier eastern Cyclades.
Afternoon: past Delos
If timing allows, a late-afternoon pass by Delos, the sacred island at the center of the Cyclades circle; in antiquity nobody was permitted to be born or to die here, a taboo strict enough that anyone close to either was ferried to the neighbouring island first.
Evening: arriving in Mykonos
You arrive in Mykonos with the evening ahead of you: the windmills, the old town, and a farewell dinner we are happy to book ahead, tables disappear fast here in season.
Overnight: Mykonos.
Don’t Miss
- A last quiet swim off Paros or Koufonisia
- Delos at golden hour
- Farewell dinner in Mykonos old town
Making This Week Work
The yacht you need
This route suits groups who want range: the empty western islands and the famous eastern ones in a single week, without retracing a mile. The mid-week legs are real distances, up to 55 nautical miles in a day, so it works best on a motor yacht or fast catamaran. A sailing yacht can do it, but you will spend most of the week motoring to hold the schedule rather than sailing.
How weather can change the week
The meltemi matters here: your captain runs the exposed crossings in the morning calm, and reorders the week around a spell rather than fighting it. Because this route runs west to east, most groups have the wind behind them by the back half of the week, which is exactly what the broker quote above is about.
Three of these days run 40 nautical miles or more; if anyone in your group is prone to seasickness, our honest answer on seasickness covers what actually helps.
Best Months to Book
- Best: June or the second half of September, when the meltemi is far softer and this route runs closest to plan
- Toughest: mid-July to mid-August, still very charterable, just build in flexibility around the Santorini and Amorgos days
The one-way fee
Budget for the one-way repositioning fee, the cost of sailing the yacht back to its base once you disembark. We quote it up front so there are no surprises; for most groups the extra cost is comfortably worth never sailing the same water twice. Our Greece charter cost guide covers what a week like this actually runs.
Want the same headline islands without the fee? The Athens to Santorini round trip covers the headline islands and returns to Athens, and the Unspoiled Cyclades route stays entirely in the quiet west.
