The Cyclades – Κυκλάδες lay in a circle (Greek: kyklos) around the sacred island of Delos, the birthplace of Apollo, and consists of 23 large islands and some 200 smaller ones. The archipelago is based on a submarine plateau which extends in an arc from the most easterly point of Attica and Evia towards the coast of Asia Minor. All the islands are hilly. The northern ones consist predominantly of Cretaceous limestone, micaceous schists, gneisses and marbles; those to the south consist in part of volcanic materials.

With the exception of Naxos the islands have no perennial rivers, and as a result of the prevailing sharp sea-winds (the Meltemi in summer) are lacking in trees. Characteristic features of the landscape are the cubed whitewashed Cycladic houses and the thatch-roofed windmills, very romantic and ideal for a sailing holiday.

Cyclades Islands

Andros, Tinos
Mykonos, Delos
Paros, Antiparos
Milos, Kimolos
Naxos town on Naxos island
Sailing, cruising and yacht charters in Santorini

To thoroughly enjoy the richness of the Cycladic islands you need at least 20 to 25 sailing days. But already a 2-week itinerary opens up much more possibilities, thus enabling you to see three times more than in a single week. When sailing 14 days:

  • The most attractive islands of Amorgos, Sifnos, Folegandros, Santorini as well as the Little Cyclades below Naxos are well in reach;
  • More opportunities to explore the often very worthwhile inlands of the islands by scooters or bikes;
  • Less time spent near the concrete outskirts of Athens;
  • A better chance to avoid the loads of fellow yachtsmen who are often herded (in flotillas) along the easy milk runs near Athens, Kea, Kythnos and Syros.
paros parikia port Naxos: view from the cave-church of Theologaki and Paros can be seen in the background kea lion

The Cyclades

The following table gives the characteristics of the Cyclades islands and you might also want to compare all the Greek regions. More dark blue stars the better.

Characteristics Northern Cyclades Southern Cyclades
Easy access by plane or ferry
Unspoiled by tourism
Beautiful ports
Amenities and tavernas
Ancient Greek sites
Mediaeval sites
Secluded anchorages
Spectacular scenery
Easy sailing conditions
Fertile and lush vegetation

The sailing itineraries

The following routes are the result of our own travels and the vast amount of suggestions from my visitors. Similar to my Ionian or Saronic routes, these Cyclades itineraries have an “off the beaten track” character and are certainly biased towards natural beauty, sequestered anchorages and ancient archaeological sites, so perhaps not suitable for all yacht charters…

Route A
Route B

Itinerary A 1 week Athens-Athens Itinerary B 1 week Athens-Athens
Day Port NM Day Port NM
1 Alimos/Kalamaki 1 Alimos/Kalamaki
2 Sounion 22 2 Kythnos Mericha 44
3 Kythnos Mericha 23 3 Syros Ermoupolis 50
4 Kythnos Loutra 20 4 Mykonos Delos 27
5 Syros Finikas 20 5 Kea 60
6 Kea 35 6 Sounion 15
7 Alimos/Kalamaki 36 7 Alimos/Kalamaki 22
156 218

Route C
Route D

Itinerary C 1 week Lavrion-Lavrion Itinerary D 1 week Lavrion-Lavrion
Day Port NM Day Port NM
1 Lavrion 1 Lavrion
2 Kythnos Mericha 23 2 Kythnos Mericha 23
3 Syros Ermoupolis 50 3 Serifos Livadi 31
4 Mykonos Delos 27 4 Sifnos Kamares 9
5 Andros Gavrion 44 5 Syros Finikas 39
6 Kea 25 6 Kea 36
7 Lavrion 17 7 Lavrion 17
186 155

Route E
Route F

Itinerary E 1 week Paros-Paros Itinerary F 1 week Syros-Syros
Day Port NM Day Port NM
1 Paros Paroikia 1 Syros Finikas
2 Sifnos Kamaras 30 2 Mykonos Delos 30
3 Folegandros 28 3 Naxos 31
4 Santorini 30 4 Paros Naoussa 9
5 Amorgos 40 5 Sifnos Kamares 42
6 Paros Naoussa 41 6 Kythnos Loutra 26
7 Paros Paroikia 10 7 Syros Finikas 19
179 157

Route G
Route H

Itinerary G 2 weeks Athens-Athens Itinerary H 2 weeks Lavrion-Lavrion
Day Port NM Day Port NM
1 Alimos/Kalamaki 1 Lavrion
2 Sounion 22 2 Kythnos Loutra 39
3 Kea 15 3 Syros Finikas 19
4 Kythnos Mericha 19 4 Paros Naoussa 24
5 Serifos 31 5 Naxos 9
6 Sifnos Kameres 9 6 Amorgos 41
7 7
8 Milos 24 8 Little Cyclades 17
9 Polyaigos 4 9 Sifnos Kamares 44
10 Paros Paroikia 33 10
11 Paros Naoussa 10 11 Serifos 9
12 Syros Ermoupolis 24 12 Kythnos Mericha 31
13 Kythnos Loutra 27 13 Kea 19
14 Alimos/Kalamaki 48 14 Lavrion 17
266 269

Route I
Route J

Itinerary I 2 weeks Paros-Paros Itinerary J 2 weeks Syros-Syros
Day Port NM Day Port NM
1 Paros Paroikia 1 Syros Finikas
2 Sifnos Kamares 30 2 Kythnos Loutra 19
3 Milos 24 3 Serifos 18
4 Polyaigos 4 4 Sifnos Kamares 9
5 Folegandros 20 5
6 Santorini 29 6 Little Cyclades 44
7 7 Amorgos 17
8 Astypalea 52 8
9 Amorgos 50 9 Donoussa 19
10 10 Naxos 28
11 Little Cyclades 17 11 Paros Naoussa 9
12 Naxos 19 12 Mykonos Delos 28
13 Paros Naoussa 9 13 Tinos 12
14 Paros Paroikia 10 14 Syros Finikas 18
264 221

Route K
Route L

Itinerary K 3 weeks Lavrion-Lavrion Itinerary L 3 weeks Athens-Athens
Day Port NM Day Port NM
1 Lavrion 1 Alimos/Kalamaki
2 Nea Marmari 25 2 Kea 36
3 Andros Gavrion 27 3 Syros Ermoupolis 39
4 Andros Kastro 31 4 Paros Naoussa 24
5 Tinos 20 5 Paros Paroikia 10
6 Mykonos Delos 12 6 Andiparos 4
7 Ikaria Evdilos 41 7 Little Cyclades 21
8 Donoussa 39 8
9 Amorgos 18 9 Ios 18
10 10 Santorini 28
11 Astypalea 49 11
12 Anafi 35 12 Sikinos 26
13 Santorini 16 13 Folegandros 8
14 14 Polyaigos 20
15 Little Cyclades 51 15 Milos 4
16 Naxos 17 16 Sifnos Kamares 24
17 Paros Naoussa 9 17
18 Paros Paroikia 10 18 Serifos 9
19 Kythnos Loutra 39 19 Kythnos Mericha 31
20 Kea Poleis Bay 10 20 Sounion 23
21 Lavrion 20 21 Alimos/Kalamaki 22
469 347

Unsorted tips

  • When particularly aiming for the Cyclades only – instead of a combination with the Saronic Gulf – the port of Lavrion is more suitable than the Alimos Marina. Starting at Lavrion, which is situated further south on Attica and much closer to Kea, means steering clear of the unsightly outskirts of Athens.
  • In the 2 or 3-weeks itineraries it is possible to have one or more rest days/stopovers/onshore excursions. Various islands like Santorini, Amorgos, Kythnos and Sifnos simply must be explored, preferably by bike or scooter.
  • How to avoid the crowds:
    • Get as far away from Athens;
    • Most yacht charters are from Saturday to Saturday, so mid week it is relatively quiet near the bases, while relatively crowded further away;
    • Medio July till end of August is main holiday season;
    • In the weekends the native Atheneans sail to Kea and Kythnos and join the tourists.
  • Overrated islands are Ios, Serifos and Mykonos. Though Serifos has a nice Chora (Livadi) and Mykonos is a handy port to visit Delos from.
Ios church amorgos katapola church tinos port

My favourite anchorages

  • Fjord bay on Amorgos island;
  • St John or Ay. Ioannis bay on Naxos island;
  • Kastro, Platis Gialos and Faros bays on Sifnos island;
  • Poleis bay on Kea island;
  • Manolonisi bay on Polyaigos island;
  • Sand bar bay on Kythnos island;
  • Naoussa bay on Paros island;
  • The anchorages in the Little Cyclades: Karos, Schinoussa, Koufonisia;
  • For the geology: south bays and coast of Milos island;
  • The flooded caldera of Santorini island: Thira, Thirasia and Kammeni.

Aegean itineraries

By popular demand an itinerary for one to three months in the whole Aegean of luxurious yacht charters, hence including the Dodecanese and Sporades.
First of all, yacht charters of more than 3 weeks render a one-way unnecessary. Furthermore, starting (and hence also ending) in Athens is easiest with flights, etc.

Therefore, starting in Athens and after spending about 10-14 days in the Saronic and Argolic gulfs cross via Hydra to Kea or Kythnos en start exploring the Aegean.
Highlights in the Cyclades are Sifnos, Paros, Naxos & the little Cyclades, Amorgos, Santorini, Milos and Folegandros. This will be a further 2 weeks: for instance Sifnos, Santorini and Amorgos are worth more than one day!!!

Cross towards the Dodecanese from Astypalea via Kasos, Karpathos to Rhodes, Symi, and continue north to the islands of Tilos, Nisyros & Kos plus Leros & Kalymnos, Patmos, Fourni, arki & Lipso and Samos.

Sailing north means beating the prevailing winds – yet the trick of this anticlockwise route is that particularly here the winds are weakest, especially on the east (the more interesting) coasts of the dodecanese and southern sporades which are sheltered by the the myriad of Aegean islands as well as the Turkish promontories.

From the Southern Sporades of Ikaria or Chios cross back into the Cyclades to Tinos & Andros, via Mykonos & Delos, Syros, Kea and Sounion and finally the Alimos/Kalamaki marina in Athens.

You can extend this basic circle easily with extra loops:

  1. South coast of the Peloponnese around the notorious Cape Maleas, worth an extra week at least;
  2. Include Crete from Thira;
  3. From Chios to Lesbos into the Northern Sporades, Limnos and Thassos;
  4. Through the Corinth Canal via the Corinth Gulf and Patras Gulf into the Ionian Sea;
  5. Cross the border and explore the Carian, Ionian and West Lycian coasts of Turkey.

One-way itineraries

There are several one-way routes possible in the Cyclades since Lavrion and Athens are upwind from the Cycladic main charter bases of Syros and Paros. Furthermore, the ports of Mykonos, Milosand Santorini increasingly serve as useful secundary bases for yacht charters as well.
Frequent domestic flights, ferries and hydrofoils connect these islands with Athens Airport and Pireaus Port.

Athens/Lavrion to Syros – 7 days

Day 0 Sat Athens or Lavrion
Day 1 Sun Kea, Main port as well as Polis bay, delightful anchorage
Day 2 Mon Andros/Tinos, Andros Port is lee-shore and involves distance, Tinos port is recommended. These islands are really off the beaten track and Gavrion and Kastro are very beautiful
Day 3 Tue Denoussa – delightful islet east of Naxos
Day 4 Wed Amorgos, Fjord bay lunch, night in Aegiali, visit northeast cliffs-800 metres sheer drop, Katapola for night (after santorini the best island in the Cyclades)
Day 5 Thu Iraklia + bays around the islets there – mini cruise area :-)
Day 6 Fri Sifnos, Kamares port; anchorages: Platis Gialos, Faros and Kastro
Day 7 Sat Syros, Ermoupolis approach even more breathtaking than the Poros approach

Athens/Lavrion to Paros – 7 days

Day 0 Sat Kea, port and anchorages (Poleis bay)
Day 1 Sun Kythnos, both Mericha and Loutra are worthwhile
Day 2 Mon Sifnos, Kamares and anchorages; Platis Gialos, Faros or Kastro
Day 3 Tue Folegandros, Karavostasi and the chora
Day 4 Wed Sikinos, Alopronia port, delightfully off the beaten track and lots of ancient ruins
Day 5 Thu Santorini, Vlichadi marina (rent scooters) and thirasia or oia, best to visit the Kameni islands by tripper boat from Skala
Day 6 Fri Naoussa on Paros, very pretty both the bay (anchorages!) as the harbour
Day 7 Sat Parikia port on Paros, charter base and ferry port

Athens/Lavrion to Syros – 10 days

Day 0 Athens or Lavrion
Day 1 Kea, main port and Poleis bay in the south east of the island
Day 2 Andros/Tinos, though usually not Andros Port (lee-shore and more distance) but likely Tinos port
Day 3 Denoussa, – delightful
Day 4 Amorgos, Fjord bay lunch, visit northeast cliffs-800 metres sheer drop, katapola for night or Aegiali
Day 5 Iraklia, Mirsini, Karos, Parianos
Day 6 Naxos, Ay Ioannis bay, Panormou or Apollonia
Day 7 Paros Naoussa,
Day 8 Sifnos, Kamares port and lunch at either Platis Gialos, Faros or Kastro (blue turquoise)
Day 9 Syros, Ermoupolis, Finikas and Delfino Bay