Start and finish your Santorini yacht charter right on the caldera, then spend seven nights island-hopping through the quieter southern and western Cyclades, without the long haul from Athens.
We recommend arriving at least a day before you board: most of our clients take a caldera-view hotel in Fira, Oia or Imerovigli first, then join the yacht at Vlychada marina on the south coast once they have had time to enjoy the viewpoints and restaurants ashore. That night is not part of the charter, it is simply the smart way to arrive.
This is an 8-day, 7-night charter. 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 Santorini, Sail to Folegandros (about 22nm)
Broker insight
Starting and ending in Santorini avoids the awkward one-way logistics, but the first morning out to Folegandros sets the tone. Pick a yacht that handles the open leg well.
Leonidas Marousos
Charter Broker
Midday: boarding at Vlychada
Board at Vlychada marina on Santorini’s south coast. Meet the crew, unpack once for the whole week, and go through the preference sheet if you have not already sent one.
Afternoon: out to Folegandros
You are not staying put. Most crews cast off within the hour, west across open water to Folegandros, a short but real crossing, so pick a yacht that handles the open leg well.
Evening: Folegandros Chora
Folegandros stayed off the radar for years thanks to its dry climate, strong winds and tiny population, and it still feels a long way from cruise-ship Greece. A short ride up from Karavostasi or Ormos Vathi takes you to the clifftop Chora, one of the most dramatic villages in the Cyclades, with an old Kastro and linked squares full of small tavernas.
Dinner
Dinner in the Chora, tables closed to cars, the walk up worth doing for the view alone.
Overnight: Folegandros.
Don’t Miss
- Wandering the clifftop Chora and Kastro quarter
- Sunset walk up to the Panagia church above the village
- Swimming at Agali, Vorina or Katergo
Day 2 – Folegandros to Milos, via Kimolos (about 25nm)
Morning: north to Kimolos
North towards Kimolos, a quiet, local island with a handful of anchorages and low-key beaches, and past Polyaigos, essentially uninhabited and protected; monk seals still use its sea caves to raise their pups, which is why we treat it as a stop to admire gently rather than a party bay.
Lunch: Kimolos
Lunch at anchor off Kimolos, or push on if the group is keen to reach Milos with the afternoon still ahead.
Afternoon: Milos
Milos delivers the drama: the white, lunar rock of Sarakiniko, the sea caves and arches of Kleftiko, and the colourful fishermen’s boathouses, syrmata, at Klima right on the waterline. It is one of those coastlines where a private yacht makes all the difference.
Evening: Kleftiko or Klima
Time at Kleftiko or Klima for caves, cliffs and syrmata houses, then dinner ashore in one of Milos’ harbor villages.
Overnight: Milos.
Don’t Miss
- Quiet anchorages around Kimolos and Polyaigos
- Sarakiniko’s white rock and turquoise water
- Kleftiko’s caves, or Klima’s syrmata boathouses
Day 3 – Milos to Sifnos (about 15nm)
Morning: a short hop to Sifnos
A short crossing north-east to Sifnos, which we often recommend to guests who care about food as much as beaches.
Lunch: Vathi, Faros or Platis Gialos
Sifnos has a long tradition of pottery and slow-cooked dishes like revithada (baked chickpeas) and mastelo (lamb in wine, in clay pots). Bays such as Vathi, Faros and Platis Gialos work beautifully as lunch and swim stops, tavernas right on the sand.
Afternoon: Kamares
For the night, Kamares makes a convenient base with easy access up to Kastro.
Evening: Kastro and the Church of the Seven Martyrs
An evening visit to Kastro, the old fortified capital, and the Church of the Seven Martyrs on its rock, before dinner trying revithada, mastelo and the local sweets.
Overnight: Kamares, Sifnos.
Don’t Miss
- Swim and lunch stops in Vathi, Faros or Platis Gialos
- Dinner trying revithada and mastelo
- Kastro and the Church of the Seven Martyrs
Day 4 – Sifnos to Paros, via Antiparos (about 20nm)
Morning: Antiparos
Back towards central Cyclades via Antiparos, all clear water and relaxed bays, ideal for a long swim, snorkel and toys session off the yacht.
Lunch: the Antiparos Cave, if you want an inland detour
The Antiparos Cave, dropping over 80 metres underground with inscriptions going back centuries, is an option if the group wants to go ashore before lunch on board.
Afternoon: Paros
A short hop to Paros, now one of the most in-demand Cyclades islands. In Parikia and Naousa you will find a mix of fishing boats and chapels alongside stylish bars and restaurants, so the evening can be as low-key or as polished as you like.
Evening: Naousa harbour
Dinner in Naousa’s harbour, where the half-submerged Venetian castle at the entrance, built by the Sommaripa family in the late 13th century, still watches over the fishing boats it was built to protect from pirate raids.
Overnight: Naousa, Paros.
Don’t Miss
- Swimming and paddleboarding in Antiparos coves
- The Antiparos Cave, if you want to go ashore
- Dinner in Naousa’s harbour, by the Venetian castle
Day 5 – Paros to Naxos (about 18nm)
Morning: a short passage east
A short passage east to Naxos, often described as the breadbasket of the Cyclades, the largest and greenest island in the group, fields, citrus groves and vineyards still very much part of everyday life.
Lunch: the west coast beaches
Lunch and a swim at one of the long west-coast beaches, Agios Prokopios, Plaka or Agios Georgios, shallow, clear water and plenty of room.
Afternoon: the old town
Above the harbour, the Venetian Kastro and the marble gate of the Portara give the island its signature outline; the doorway was begun in the 6th century BC by the tyrant Lygdamis for what was meant to be the largest temple in the Aegean, and abandoned mid-build when he was overthrown.
Evening: dinner in the old town
Dinner in the old town, with a taste of Naxian potatoes, local cheeses, and kitron liqueur if anyone wants to try it.
Overnight: Naxos.
Don’t Miss
- Beach time on the west coast
- The Portara at golden hour
- Naxian potatoes and kitron liqueur
Day 6 – Naxos to Koufonisia and Schinousa (about 28nm)
Morning: into the Small Cyclades
East into the Small Cyclades, almost purpose-built for yachts: short hops, turquoise water, very little development.
Lunch: Koufonisia
Ano Koufonisi has a small port village and a chain of beaches, Pori, Italida, Fanos, full of sea caves and natural pools; crews know exactly where to tuck in for the best swimming.
Afternoon: Kato Koufonisi
Kato Koufonisi is uninhabited, a quiet anchorage for a long, lazy swim before moving on.
Evening: Schinousa
Schinousa, a tiny island south of Naxos, runs on a slow, easy rhythm. Most beaches are an easy walk or short tender ride from the Chora, and the evening usually distils down to: swim, shower, taverna, stars.
Overnight: Schinousa.
Don’t Miss
- Sea caves and rock pools at Koufonisia
- A quiet swim at uninhabited Kato Koufonisi
- A simple village taverna dinner on Schinousa
Day 7 – Koufonisia and Schinousa to Ios (about 26nm)
Morning: south to Ios
South to Ios, an island with a dual identity: famous for its nightlife, but also home to some of the best beaches in the Cyclades.
Lunch: Mylopotas or Manganari
Lunch and toys at Mylopotas or Manganari, whichever suits the group’s energy today.
Afternoon: Ios Chora
Ios Chora is a maze of steps, small squares and churches; higher still, Panagia Gremiotissa and the supposed Tomb of Homer both offer wide views over the Aegean.
Evening: choose your own energy
This is usually a “choose your own energy” stop, some guests lean into the cocktail bars, others keep it to beaches and viewpoints and an early dinner.
Overnight: Ios.
Don’t Miss
- Beach and toys at Mylopotas or Manganari
- Ios Chora’s lanes and churches
- Sunset at Gremiotissa or the Tomb of Homer
Day 8 – Ios to Santorini, Return (about 22nm)
Morning: the run back
A short run back to Santorini, which keeps departure day calm rather than rushed.
Late morning: last swim
There is usually time for a last swim and an unhurried breakfast or lunch at anchor before the final approach.
Midday: back to Vlychada
The yacht returns to Vlychada marina for disembarkation.
Departure
We generally suggest planning at least one more night ashore, either back on the caldera or in Athens, rather than aiming for a tight long-haul connection the same day.
Don’t Miss
- A calm, unrushed final morning
- One last swim before disembarkation
- One more night on the caldera before you fly
Making This Week Work
The yacht you need
Starting and ending on Santorini avoids the awkward one-way logistics of a route that finishes somewhere else, no repositioning fee, no separate flight home from a different island. The first morning out to Folegandros is a real open-water leg, so a motor yacht or fast catamaran with real cruising speed makes the whole week more comfortable, though the legs after that stay short.
Santorini has its own tradeoff on the other end: Vlychada’s marina is small and provisioning runs slower in peak season than the quieter islands you will visit later, and some boarding transfers happen by dinghy rather than stepping straight off a quay. Worth confirming with your broker what to expect for your specific yacht before you book flights.
How weather can change the week
The meltemi matters here too: your captain runs the exposed crossings in the morning calm and reorders the week around a real spell rather than fighting it. Every stop after Santorini gets quieter and more sheltered as the week goes on, Folegandros, Kimolos, Sifnos, the Koufonisia channel, which many of our clients say is exactly the right direction for a week to move in.
If anyone in your group is prone to seasickness, our honest answer on seasickness covers what actually helps, most of this route’s legs are short once the first day is behind you.
Best Months to Book
- Best: June or the second half of September, when the meltemi is far softer
- Toughest: mid-July to mid-August, still very charterable, just build in flexibility around the first crossing
Santorini’s airport is well connected in season, and our Greece charter cost guide covers what a week like this actually runs.
Prefer to end on the famous islands instead of starting there? The Athens to Santorini route runs the week the other way around.
