Itinerary · 10 days · 51 places
10 Days in the Cyclades
Ten days across three Cycladic islands: first the Santorini caldera with Oia, Akrotiri and the vineyards around Pyrgos, then the mountain villages and west-coast beaches of Naxos, and finally Mykonos with a whole day on Delos.
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Photo: Pixabay · Pexels
The route on the map
The plan, day by day
Day 1Arrival above the caldera
Arrival in Santorini
Hotel check-in
Fira sits high on the crater rim: bus station, bakeries and the caldera path are all within walking distance, and the rooms at the back are the quieter ones.
Caldera path from Fira to Firostefani
Paved path running right along the cliff edge, with views of the Nea Kameni volcanic cone and the ships anchored far below.
Firostefani viewing terrace
The church of Agios Gerasimos stands on a ledge from which you can see Fira, Imerovigli and the whole bay at once.
Evening: Erythrou Stavrou bar lane in Fira
The lane behind the cathedral is lined with wine bars and small restaurants and only fills up after sunset.
Day 2Oia and the north of the island
Byzantine castle ruins in Oia
From the remains of the castle walls the view sweeps over the white cave houses to the island of Thirasia opposite.
Oia Maritime Museum
In an old captain's house, ship models, logbooks and photos tell of the days when Oia lived off its merchant fleet.
Ammoudi Bay
Around 280 steps lead down from the village to the red-rock harbour with its fishing boats and the jumping rock opposite.
Baxedes beach
Long, barely developed shingle beach on the north coast with tamarisks for shade and calmer water than in the south.
Finikia village
Ten minutes' walk east of Oia, a hollow of old winegrowers' houses where nothing has been dressed up for tourists.
Evening: Marmara lane in Oia
The marble main lane is lit up after sunset and empty enough for you to really see the façades.
Day 3Akrotiri and the black south coast
Akrotiri archaeological site
Under a protective roof stands a Bronze Age town with two-storey houses and streets, preserved by the volcanic eruption of 1600 BC.
Akrotiri lighthouse
On the far south-western tip, the 1892 lighthouse stands above the cliffs with a view over the entire crater bay.
Red Beach
A rust-red lava wall plunges straight into turquoise water; the view from the lookout is more impressive than the narrow beach itself.
Tomato Museum in Vlychada
The old tomato-paste factory of 1945 stands with its boilers and canning presses just as it was when it closed in 1981.
Vlychada beach
Wind-sculpted white cliffs rise like a lunar landscape behind the dark shingle beach.
Evening: Vlychada marina
The small marina stays local in the evening: a few tables by the water, fishermen mending nets, no tour crowds.
Day 4Vineyards, Ancient Thera and Kamari
Pyrgos hill village
From the Venetian kastro at the top you overlook both coasts; the lanes below wind in rings around the rock.
Santo Wines winery
On the terrace above the caldera, Assyrtiko and Vinsanto are poured from the island's basket-trained vines that coil low to the ground.
Ancient Thera on Mesa Vouno
At 360 m, the agora, theatre and houses of the Dorian city lie on a ridge between two bays.
Kamari beach promenade
Black shingle beach beneath the sheer rock face of Mesa Vouno, with a car-free promenade behind it.
Evening: Kasteli lanes in Emporio
Emporio's medieval labyrinth is lit up and almost empty in the evening — the houses themselves form the fortress wall.
Day 5Crossing to Naxos and the Chora
Onward to Naxos
Hotel check-in
Portara at Naxos harbour
The free-standing marble gateway of an unfinished temple of Apollo from 530 BC stands on the harbour islet of Palatia.
Kastro of Naxos Town
The Venetian upper town, with coats of arms above the doorways, the Glezos Tower and a Catholic cathedral in the middle of the residential quarter.
Archaeological Museum of Naxos
In the former Jesuit college, Cycladic marble idols from the 3rd millennium BC stand in neat rows.
Agios Georgios beach
Gently shelving town beach south of the harbour, ideal for a late swim without any travel.
Evening: Naxos Town harbour promenade
The Protodikiou waterfront fills with locals after sunset; from here you can see the Portara glowing across the water.
Day 6Mountain villages of the interior
Chalki hill village
The old main village of the Tragea plain: the Vallindras citron liqueur distillery, olive groves and a few Byzantine churches among the tower houses.
Filoti village
The island's largest mountain village, built in terraces at the foot of Mount Zas, with a plane-tree square and views across the whole Tragea.
Panagia Drosiani near Moni
One of the oldest churches in the Aegean, from the 6th century, with layer upon layer of frescoes in its rock-like domes.
Apeiranthos marble village
The lanes are paved entirely with marble slabs; the villagers speak their own dialect with a Cretan flavour.
Archaeological Museum of Apeiranthos
Small village museum with incised marble slabs from the 3rd millennium BC depicting hunters and boats.
Evening: Filoti village square
In the evening the old men sit at the kafenio under the big plane tree while the church of Panagia Filotitissa is floodlit.
Day 7Temples, kouroi and the west-coast beaches
Temple of Demeter near Sangri
A marble temple from 530 BC re-erected from its original parts, standing alone above barley fields.
Kouros of Flerio near Melanes
An unfinished statue of a youth, a good six metres long, has lain in the quarry garden where it broke since antiquity.
Agia Anna beach
Fine pale sand behind a small fishing harbour, with tavernas right at the water's edge.
Plaka beach
Four kilometres of dune beach with cedar bushes, largely undeveloped and shallow enough to wade far out.
Cape Mikri Vigla
Rocky headland between two bays: to the north the kitesurfers tug at the meltemi, to the south it is sheltered from the wind.
Evening: Agios Prokopios beach bars
The waterfront strip behind the beach stays open until late, with views back to the lights of the Chora.
Day 8Crossing to Mykonos and the Chora
Onward to Mykonos
Hotel check-in
Kato Mili windmills
Seven round thatched mills stand on the hill above the town and ground grain for the ships until the 20th century.
Panagia Paraportiani
Five chapels from the 15th to 17th centuries built into one another, whitewashed into a single curving sculpture.
Little Venice
Captains' houses with wooden balconies stand right in the surf; when the wind is up, the sea sprays onto the terraces.
Archaeological Museum of Mykonos
Shows mainly the finds from Rheneia, plus the storage jar found on Mykonos with one of the oldest known depictions of the Trojan Horse.
Megali Ammos beach
The town beach south-west of the Chora, fifteen minutes on foot and sheltered from the wind in the afternoon.
Evening: Matogianni lane
The Chora's narrow main lane with bars, jewellery shops and the famous pelicans still wandering around in the evening.
Day 9Delos and the island interior
Delos archaeological site
The uninhabited island was a sanctuary of Apollo and a trading hub for 25,000 people; the theatre quarter, houses with mosaics and the temple precinct lie open.
Terrace of the Lions on Delos
On the terrace above the sacred lake stand copies of the Naxian marble lions from the 7th century BC.
Archaeological Museum of Delos
Home to the original lions, along with sculptures and household objects from the Hellenistic trading city.
Panagia Tourliani Monastery in Ano Mera
Baroque marble bell tower and a carved iconostasis from Florence behind white walls on the village square.
Agios Sostis beach
Undeveloped bay in the north with no sunbeds or electricity, but clear water and views of Tinos.
Evening: Ano Mera village square
The island's only real village square: tables under trees in front of the monastery, without the bustle of the Chora.
Day 10One last bay and departure
Ornos beach
Sheltered bay with calm water, ten minutes by car from the airport — the most practical last swimming spot.
Agios Ioannis Bay
From the small chapel on the slope you look across the strait straight to Delos, where yesterday's excursion began.
Departure from Mykonos
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