Sailing itineraries Cyclades

1-weeks Athens: A, B, C, D
2-weeks Athens: E, F
3-weeks Athens: G
3-weeks AthensParos: H
1-weeks Paros: I, J, K, L
2-weeks Paros: M, N
3-weeks Paros: O, P

The optimised routes on the right are the result of our own sailing trips plus numerous suggestions from my visitors. Crucially, these sailing itineraries prioritise historic & authentic ports and tranquil anchorages with a focus on culture and archaeology, above popular tourist destinations like Mykonos.

The cornucopia of Cycladic islands includes many must-see ports and anchorages; below you find a (personal) selection divided into “truly must-see” and “highly recommended” categories.
Anchorage.
Mooring buoy(s) available.
Marina, port, or at least a quay to take a line to.
Note that in the main yacht charter season there is a shortage of berths, which can be critical when the Meltemi wreaks havoc. Since reserving berths is mostly not possible, it is best to arrive early (before 14:00) or you will have to anchor nearby.

Truly must-see

Kea: Poleis
Kythnos: Merichas
Kythnos: Flampouria
Syros: Ermoupoli
Syros: Grammata
Andros: Achla
Andros port (Chora or Kastro)
Tinos port
Tinos: Koumelas
Rineia: Skinos
Rineia: Miso / Ampelia
Delos
Serifos: Livadi / Chora
Serifos: Platis Gialos
Serifos: Psili Ammos
Sifnos: Kastro
Sifnos: Faros / Apokofto / Chrisopigi
Sifnos: Fikiada
Paros: Naousa
Paros: Parikia
Andiparos port
Despotiko: Gamma cove
Despotiko: Livadi
Naxos town
Naxos: Kalantos
Glaros / Glaronisi
Drima Antikeros
Schinoussa: Myrsini
Irakleia: Alimia
Milos port (Adamas)
Milos: Kleftiko
Polyaigos: Ammoura
Polyaigos: Manolonisi
Folegandros: Karavostasi
Sikinos: Alopronia
Ios: Tris Klises
Ios port
Amorgos: Katapola
Amorgos: Katapola Xilokeratidi
Amorgos: Aegiali
Amorgos: Megali Vlichada
Santorini: Vlychada marina
Santorini: Akrotiri
Thirasia: Ag Nikolaos
Anafi port Skala

Highly recommended

Kea: Ag Nikolaos (Ioulis)
Kea: Otzias
Kea: Pisses
Kythnos: Ag Ioannis & Stefanos
Kythnos: Kanala
Kythnos: Mavrianou
Syros: Didyma / Gaidaros
Syros: Mega Gialos & Ampelas
Syros: Galissas
Andros: Gavrio
Andros: Fellos
Tinos: Ag Romanou
Tinos: Isternion
Mykonos port
Rineia: Karmou Ammos
Serifos: Sikamia
Sifnos: Kamares
Sifnos: Platis Gialos
Sifnos: South-East Bay
Sifnos: Vathi
Paros: Piso Livadi
Despotiko channel
Strongyli
Naxos: Azala
Naxos: Moutsouna
Donousa port
Donousa: Kedro / Dendro
Donousa: Roussa
Pano Koufonisi: Pori
Pano Koufonisi marina
Kato Koufonisi: Kato “South bay”
Irakleia: Ag Georgios
Milos: Dimitrios Cove
Milos: Tsigrado
Kimolos: Prasonisi
Kimolos: Psathi
Polyaigos: South coast
Folegandros: vathy
Sikinos: Ag Georgios
Ios: Agia Theodotis
Ios: Manganari
Ios: Trypiti
Amorgos: Gramvousa
Amorgos: Kalotiri
Santorini: Skala • Fira
Thirasia: Riva
Anafi: Megas Potamos
Anafi: Livoskopos

Starting ports Northern or Southern Cyclades

The majority of sailing holidays start from Athens which has several yacht charter bases: Alimos / Lavrion / Olympic marina…

Starting here allows the vital alternative of sailing the Argolic / Saronic Gulfs in case the weather forecast for the Cyclades is grim.

The major downside is that you can only reach the Northern Cyclades in a single week from Athens. In fact, even in two weeks the southernmost islands are remote.

So, in order to visit the Southern Cyclades in “just” seven days, you will need to start within the Cyclades. In which case Paros is the obvious yacht charter base. However, also consider minor bases such as Mykonos Tourlos, Syros, or even Santorini and Milos.

One week or longer…

In 2 weeks you will see 3 times as much as in 1 week which allows you:

to set sail from Athens while still having the islands within reach. Starting from Athens means more safety, flexibility and choice in yachts & catamarans.
to circumnavigate Andros and Tinos, or – even more off the beating track – continuing east, crossing into the Eastern Sporades and visiting Ikaria, Patmos, Chios, etc…
the time to explore the island's interior – wildlife, Chora, scenery and the archaeological sites – see my extensive list of shore excursions.
to comfortably reach the Lesser Cyclades, or Milos, Sifnos, Ios from the mainland, as well as from Paros reach Anafi, Thira / Thirasia, Astypalaia and Amorgos, or to cross to the Argolic Gulf, visiting Monemvasia, Kyparissi and Ierakas.
more opportunities to steer clear of the slacking charters fleets (and a few flotillas) that sail milk runs: evidently you should avoid the milk runs

The following tables give the characteristics of the Northern and Southern Cyclades, and you might also want to compare the other Greek regions with the Cycladic yacht charter areas. More stars mean that a statement is more true.

Northern Cyclades

Characteristics
Easy access by plane / ferry
Unspoiled by tourism
Picturesque ports
Tavernas & facilities
Ancient Greek sites
Medieval sites
Secluded anchorages
Sublime scenery
Easy sailing conditions
Fertile & lush vegetation
Wildlife

Northern Cyclades

Southern Cyclades

Southern Cyclades

A	1 week Athens – Athens	View
Day	Port	NM
1	Athens
2	Sounion	24
3	Ag Nikolaos on Kea	15
4	Ermoupoli on Syros	40
5	Loutra on Kythnos	31
6	Mericha on Kythnos	12
7	Athens	47
		169

Yacht charters: Route A Athens simple — **A – First time bareboat in the Cyclades** • one night at anchor in Sounion • short legs, although this “shortest” Cycladic route still has twice the mileage of a regular Ionian route; compare **Corfu route A** and **Lefkas routes G**, H and I • sail clockwise or counterclockwise according to the **weather forecast**, but in order to reach Mericha before dusk the handover of your yacht should be in the early afternoon, otherwise sail from Athens to Pisses anchorage, 38 NM.
In the bay of Ag Nikolaos on Kea you will find Korissia (Livadi) & Vourkari ports from where you can expore Ioulis aka Chora.
Lunch anchorages at Pisses, Poleis and Otzias on Kea; Grammata, Mega Gialos & Ampelas and Megali Agkali on Syros; all around Kythnos; Sounion • in the charter season you are urged to arrive before 14:00 to secure an appropriate berth • optionally go south of Kythnos and visit one of the many striking anchorages: Ag Ioannis, Kanala, Mavrianou and in particular Flampouria for lunch and swimming: via the southern Cape of Ag Dimitris, the distance Loutra to Mericha increases by 9 NM to 21 NM.

B	1 week Athens – Athens	View
Day	Port	NM
1	Athens
2	Ag Nikolaos on Kea	40
3	Loutra on Kythnos	23
4	Livadi on Serifos	24
5	Faros on Sifnos	19
6	Mericha on Kythnos	42
7	Athens	46
		194

Yacht charters: Route B Athens South or East with every night in port — **B – Southbound or eastbound with every night in port** • no nightly anchorages • medium distances with some proper sailing legs • the **navy** coloured route is the southbound option • lunch-stops at Poleis on Kea; Ag Ioannis, Kanala, Flampouria and Sandbar bay (near Mericha) on Kythnos; Sikamia, Platis Gialos and Psili Ammos on Serifos; Kastro, South-East Bay, Fikiada, Vathi and Chrisopigi / Apokofto on Sifnos; Sounion on the last leg to Alimos.
The **fuchsia** coloured route is the eastbound option:
Ag Nikolaos Gavrio on Andros 25 NM,
Gavrio on Andros Tinos port 30 NM,
Tinos port Ermoupoli 12 NM,
Ermoupoli Mericha 41 NM, **Tot. 194 NM**, precisely as long as the southbound itinerary.
Appropriate lunch stop anchorages specific for the eastbound route section: Batsi on Andros; Koumelas, Ag Romanos etc., Isternion on Tinos; Megali Agkali and Mega Gialos & Ampelas on Syros.

C	1 week Athens – Athens	View
Day	Port	NM
1	Athens
2	Sounion	24
3	Flampouria on Kythnos	25
4	Apokofto / Chrisopigi on Sifnos	41
5	Platis Gialos on Serifos	22
6	Poleis on Kea	25
7	Athens	43
		180

Yacht charters: Route C Athens southbound, all anchorages — **C – Southbound, all anchorages** • medium distances, possibly advanced sailing • if the weather forecast is grim, you can easily adjust the itinerary to nearby ports: Loutra, Mericha, Faros, Kamares, Livadi.
The **fuchsia** coloured legs are extra venturous yet, also because of the **archaeological significance of Despotiko**, very worthwhile:
Flampouria Manolonisi 41 NM,
Manolonisi Livadi / Gamma on Despotiko 25 NM,
Livadi / Gamma on Despotiko Poleis 50 NM, **Tot. 208 NM**.
You can use Spathi on Kimolos as a safe port near Manolonisi on Polyaigos.
Lunch-stops: all around Polyaigos, Kastro, South-East Bay, Fikiada and Vathi on Sifnos; Ag Ioannis, Kanala and Sandbar bay on Kythnos; Sounion on the way back to Alimos; Sikamia and Psili Ammos on Serifos; Pisses on Kea.

D	1 week Athens – Athens	View
Day	Port	NM
1	Athens
2	Sounion	24
3	Ermoupoli on Syros	55
4	Skinos on Rinea • Delos	17
5	Loutra on Kythnos	40
6	Poleis on Kea	10
7	Athens	43
		189

Yacht charters: Route D ESE, Delos & top anchorages — **D – Delos • Rineia & finest anchorages** • medium to long distances, allowing real sailing • 3 or 4 nights at anchor • key is provisioning at Ermoupoli, followed by a short leg in order to have maximum time exploring the Delos archaeological sites • the leg around the *north* cape of Kea when sailing from Sounion to Syros is also 55 NM and allows you to have a swim + lunch at Otzias • optionally swap Poleis for Pisses on Kea.
The **fuchsia** coloured route brings you around the *south* cape of Kythnos, with anchoring in Sandbar bay instead of going to Loutra port:
Rinea • Delos Sandbar bay 50 NM,
Sandbar bay Poleis 10 NM, **Tot. 199 NM**.
Lunch anchorages: Prison bay on Yiaros; Isternion and Ag Romanou on Tinos; Grammata and Didyma / Gaidaros and Mega Gialos & Ampelas on Syros; Ag Ioannis & Stefanos, Kanala, Mavrianou and Flampouria on Kythnos; Kavia, Pisses and Vroskopos on Kea.

E	2 weeks Athens – Athens	View
Day	Port	NM
1	Athens
2	Sounion	24
3	Ag Nikolaos on Kea	15
4	Andros port	48
5	"	–
6	Tinos port	27
7	Skinos on Rineia • Delos	13
8	Andiparos port	23
9	Despotiko	14
10	Fikiada on Sifnos	17
11	"	–
12	Livadi on Serifos	18
13	Mericha on Kythnos	26
14	Athens	47
		272

Yacht charters: Route E Eastbound archaeology + Delos, Andiparos and Despotiko — **E – Eastbound archaeology + Delos, Andiparos and Despotiko** • 3 nights at anchor • short distances except for 2 legs with medium distances • 2 rest/excursion days • the Antiparos Strait is for calm weather and without any swell only • Fikiada can be swapped with Vathi or Kamares • on Despotiko you can either choose Gamma cove or Livadi.
The **fuchsia** leg means one extra shore day (to explore Tinos island):
Ag Nikolaos Tinos port 44 NM, **Tot. 241 NM**.
Lunch and swimming bays: Ateni; Rozou, Achla on Andros; Koumelas, Isternion and Ag Romanou on Tinos; Kastro on Sifnos; Sikamia on Serifos; Mavrianou and Flampouria on Kythnos.
Specific to the fuchsia leg: Prison bay on Yiaros; Koumelas and Isternion on Tinos; Grammata on Syros.

F	2 weeks Athens – Athens	View
Day	Port	NM
1	Athens
2	Flampouria on Kythnos	49
3	Kamares on Sifnos	32
4	"	–
5	Psathi port on Kimolos	14
6	Manolonisi on Polyaigos	2
7	Karavostasi on Folegandros	23
8	"	–
9	Ios port	18
10	"	–
11	Despotiko	20
12	Ermoupoli on Syros	33
13	Pisses on Kea	45
14	Athens	38
		274

Yacht charters: Route F Athens southbound counterclockwise — **F – Southbound** • short distances except 3 medium legs, quite advanced due to the typically stronger winds and higher waves in the southern Cyclades • 3 rest/excusion days • 3 nights at anchor • usually diving down to Milos is done counterclockwise • if the pontoon is present at Alopronia be sure to explore Sikinos • the penultimate leg to Pisses is 45 NM sailing south of Syros, or 43 NM via north Syros.
Suggested swimming + lunch bays: Sikamia, Megalo Livadi on Serifos; Vathy, Fikiada and SE bay on Sifnos; Vathi on Folegandros; Alopronia and Ag Georgios on Sikinos; Mega Gialos & Ampelas on Syros; Poleis on Kea.
The **red** section uses one rest day to circumnavigate Milos:
Psathi Adamas 14 NM,
Adamas Kleftiko 16 NM,
kleftiko Karavostasi 33 NM, **Tot. 312 NM**, which is 38 NM longer than the main navy coloured itinerary. Lunch-stop at Tsigrado on Milos.
The **fuchsia** leg also takes one rest day in order to visit Tris Klises on Ios:
Karavostasi Tris Klises 23 NM,
Tris Klises Ios port 11 NM, **Tot. 280 NM**, an extra 6 NM. Suggested lunch-stops at Tsigrado on Milos; Manganari and Trypiti on Ios.

G	3 weeks Athens – Athens	View
Day	Port	NM
1	Athens
2	Sounion	24
3	Poleis on Kea	20
4	Tinos port	40
5	"	–
6	Skinos on Rineia • Delos	13
7	Stavros on Donousa	32
8	Aegiali on Amorgos	15
9	Katapola on Amorgos	11
10	"	–
11	Myrsini on Schinoussa	19
12	Anafi port	41
13	Vlichada on Santorini	17
14	"	–
15	Tris Klises on Ios	30
16	Ios port	11
17	"	–
18	Faros on Sifnos	29
19	Livadi on Serifos	22
20	Flampouria on Kythnos	25
21	Athens	49
		398

Yacht charters: Route G Athens three weeks into the Cyclades — **G – Proper sailing: Amorgos, Santorini, Delos** • 4 rest/excursion days • 4 nights at anchor • only 3 longer legs, yet sailing in the southern Aegean (Santorini, Anafi) can be very challenging.
Selected lunch-stop anchorages: Grammata on Syros; Isternion and Ag Romanou on Tinos; Dendro and Roussa on Donousa; “Fjord bay”, Kalotiri and Gramvousa on Amorgos; Drima-Antikeros and Alimia in the Lesser Cyclades; Megas Potamos on Anafi; Akrotiri and Kameni on Santorini; Manganari and Trypiti on Ios; Despotiko; Sikamia on Serifos; Pisses on Kea.

H	3 weeks Athens – Paros oneway	View
Day	Port	NM
1	Athens
2	Poleis on Kea	44
3	Ag Ioannis on Kythnos	15
4	Livadi on Serifos	19
5	"	–
6	Adamas on Milos	28
7	Kleftiko on Milos	15
8	Karavostasi on Folegandros	32
9	Nikolaos on Thirasia	24
10	"	–
11	Vlichada on Thira	10
12	Skala on Anafi	17
13	"	–
14	Aegiali on Amorgos	51
15	Katapola on Amorgos	11
16	"	–
17	Koufonisi marina	14
18	Kalantos on Naxos	6
19	"	–
20	Naoussa port on Paros	24
21	Parikia on Paros	11
		321

Yacht charters: Route H Athens to Paros oneway — **H – Athens to Paros** • practically all the gems of the Cyclades • some proper sailing • 5 rest/excursion days • just 3 nights at anchor • southern part can possibly be very daunting due to higher prevailing winds and waves, mind the **Etesians**.
Handpicked lunch-stop anchorages: Ag Ioannis and Kanala on Kythnos; Platis Gialos and Psili Ammos on Serifos; Dimitrios and Tsigrado on Milos; Akrotiri on Santorini; Megas Potamos on Anafi; “Fjord bay” and Kalotiri on Amorgos; Glaros and Kato South bay in the Lesser Cyclades; Piso Livadi and Naoussa bay (Ag Ioannou) on Paros;
The **fuchsia** coloured section brings you to Sikinos and Ios instead of Milos:
Livadi Karavostasi 39 NM,
Karavostasi Alopronia 11 NM,
Alopronia Ios port 7 NM,
Ios port Thirasia 19 NM, **Tot. 298 NM**, which is 23 NM shorter than the main navy coloured itinerary. Lunch, swimming and snorkeling: Vathi, Fikiada and South-East Bay on Sifnos; Chryssospilia on Folegandros; Ag Georgios on Sikinos; Trypiti on Ios.
If you don't find Alopronia's pontoon installed, proceed to Ios port.
The **red** section uses one rest day to include the archaeological site of Despotiko and Andiparos port instead of Naoussa:
Kalantos Despotiko 24 NM,
Despotiko Antiparos 14 NM,
Antiparos Parikia 5 NM, **Tot. 329 NM**, which is just 8 NM longer than the main navy coloured itinerary.

Sailing routes Paros island

Parikia port is the largest base, but there are often also a few yacht charters offered from Naousa port ("marina") or from the mini-port of Piso Livadi.
The routes below use Parikia as start / end, yet can easily be adapted when starting from Naousa or Piso Livadi.

I	1 week Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Andiparos port	5
3	Livadi on Despotiko	14
4	Ios port	20
5	Tris Klises on Ios	11
6	Myrsini on Schinoussa	14
7	Parikia on Paros	35
		99

Yacht charters: Route I Paros 1 week easy (not through andiparos strait) family sailing, easy. — **I – Easy sailing to Ios** • all very short legs, family cruising • 2 nights at anchor, yet in adverse weather you can substitute Tris Klises & Livadi for Kalantos & Naoussa ports, which also shortens the last leg.
Avoid the Antiparos Strait.
Preferred lunch and swimming anchorages: Ag Georgios on Sikinos; Trypiti and Agia Theodotis on Ios; Alimia on Irakleia, Naoussa bay.
See **Routes J** & K for similar carefree itineraries!

J	1 week Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Naoussa on Paros	11
3	Alimia on Irakleia	26
4	Myrsini on Schinoussa	7
5	Koufonisi marina	11
6	Kalantos on Naxos	7
7	Parikia on Paros	32
		94

Yacht charters: Route J Short distances and easy family sailing to the Lesser Cyclades — **J – Easy / moderate sailing to the Lesser Cyclades** • very short distances, easy sailing, suitable for small children • only one night at anchor (Alimia), which can be circumvented by opting for e.g. Ag Georgios port on Irakleia.
The **fuchsia** coloured route suggests Alimia as a lunch anchorage and continues on to the Drima-Antikeros anchorage for the night, and allows you to reach Katapola on Amorgos the next day!
Naoussa Drima-Antikeros 39 NM,
Drima-Antikeros Katapola 9 NM,
Katapola Koufonisi Marina 14 NM, **Tot. 112 NM**, 18 NM longer than the main navy coloured itinerary.
Swimming / snorkeling options: Agia Theodotis on Ios; Gramvousa on Amorgos; Kato Koufonisi south, Glaros, Pori on Pano Koufonisi in the Lesser Cyclades.

K	1 week Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Myrsini on Schinoussa	36
3	Drima-Antikeros	11
4	Katapola on Amorgos	9
5	Aegiali on Amorgos	11
6	Stavros on Donousa	15
7	Parikia on Paros	38
		120

Yacht charters: Route K easy sailing east to Amorgos and Lesser Cyclades — **K – East: Amorgos & carefree** • 1 night at anchor easily dodged by continuing to Katapola • mostly short legs and easy sailing, safe with (small) children • Amorgos and lesser Cyclades as main focus • clockwise or counterclockwise depending on **weather forecast**, also see **VHF, OLYMPIA, NAVTEX**. Suggested lunch and snorkeling anchorages: Despotiko; Kato and Pano Koufonisi, Glaronisi in the Lesser Cyclades; Alimia on Irakleia; Gramvousa and “Fjord bay” and Kalotiri on Amorgos; Dendro and Roussa on Donousa.

L	1 week Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Karavostasi on Folegandros	33
3	Vlichada on Santorini	29
4	Anafi port	17
5	Katapola on Amorgos	40
6	Ios port	35
7	Parikia on Paros	42
		196

Yacht charters: Route L South Ionian route of Anchorages — **L – Highlights of the (SE) Cyclades proper sailing** • advanced even for the Cyclades • getting the most out of 1 week sailing • no nights at anchor, yet incentive to go night sailing.
The passage in **red** through the shallow <3.5m and very narrow Antiparos Strait is an adventure for a calm day motoring and without any swell.
The **fuchsia** coloured route means night sailing from Karavostasi to Thirasia, and circumnavigating Amorgos; the vertical cliffs of NE Amorgos are truly spectacular, another must-see is the **Monastery** from the water.
Karavostasi Thirasia 24 NM,
Skala on Anafi Around Amorgos to Katapola 58 NM.
Lunch and snorkeling options: Stroggili + Despotiko; Agia Theodotis and Trypiti on Ios; Drima-Antikeros; Gramvousa on Amorgos; Piso Livadi + Marmara and Naoussa bay on Paros, furthermore if circumnavigating Amorgos also “Fjord bay”.

M	2 weeks Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Livadi on Despotiko	14
3	Karavostasi on Folegandros	21
4	"	–
5	Vlichada on Santorini	29
6	"	–
7	Tris Klises on Ios	24
8	Ios port	11
9	"	–
10	Myrsini on Schinoussa	21
11	Kalantos on Naxos	5
12	Naxos port	17
13	Naoussa on Paros	9
14	Parikia on Paros	11
		162

Yacht charters: Route M Central and South Cyclades: Santorini 2 weeks — **M – Central and South Cyclades: Santorini** • 3 rest/excursion days • focus on Naxos island, Santorini, and the other top ports, with just 2 nights at anchor (Despotiko and Tris Klises), which are easily omitted in case of bad weather for nearby ports (e.g. Antiparos and Ios port).
The **fuchsia** coloured legs use 2 rest/excursion days to cover Alopronia (if pontoon is installed) and Anafi.
Karavostasi Alopronia 11 NM,
Alopronia Vlichada 26 NM,
Vlichada Skala on Anafi 17 NM,
Skala on Anafi Tris Klises 27 NM.
Suggested lunch + swimming anchorages: Chryssospilia on Folegandros; Akrotiri on Santorini; Trypiti and Agia Theodotis on Ios; Alimia on Irakleia; Pisa livadi / Marmara and Naoussa (Ag Ioannis) on Paros;

N	2 weeks Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Ermoupoli on Syros	25
3	Tinos port	12
4	"	–
5	Skinos on Rineia • Delos	13
6	Stavros on Donousa	32
7	“Fjord bay” on Amorgos	15
8	Katapola on Amorgos	13
9	"	–
10	Drima-Antikeros	9
11	Myrsini on Schinoussa	11
12	Ios port	21
13	"	–
14	Parikia on Paros	34
		185

Yacht charters: Route N East Cyclades 2 weeks — **N – East Cyclades (including Anafi)** • 4 of the best anchorages to spend the night in the south Aegean • each port is a major highlight, with 3 rest/excursion days to explore the interiors of the islands.
The **fuchsia** coloured legs include Anafi; sailing “under” the immense cliffs of NE Amorgos is spectacular, and so is rounding Cape Kalamos of Anafi.
“Fjord bay” Skala on Anafi 45 NM,
Skala on Anafi Ios port 35 NM.
The best lunch anchorages: Ag Georgios on Sikinos; Stroggili + Despotiko; Azala or Moutsouna on Naxos; Dendro and Roussa on Donousa; Kalotiri and Gramvousa on Amorgos; Livoskopos and Mega Potamos on Anafi; Alimia on Irakleia; Kato Koufonisia South Bay;

O	3 weeks Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Skinos on Rineia • Delos	20
3	Tinos port	13
4	"	–
5	Andros port	32
6	Ermoupoli on Syros	28
7	Kalantos on Naxos	45
8	"	–
9	Ag Georgios on Irakleia	5
10	Myrsini on Schinoussa	2
11	Katapola on Amorgos	19
12	"	–
13	Aegiali on Amorgos	11
14	“Fjord bay” on Amorgos	5
15	Anafi port	47
16	"	–
17	Tris Klises on Ios	27
18	Ios port	11
19	Alimia on Irakleia	14
20	Despotiko	22
21	Parikia on Paros	14
		315

Yacht charters: Route O All the highlights of the east Cyclades — **O – East Cyclades** with three options:

The main **navy blue** coloured route encompasses Andros in the very north and Anafi in the very south plus the circumnavigating of Amorgos.
In **red** an alluring extension to remote **Astypalaia**; worth 2+ days.
The **fuchsia** coloured route features Santorini, Thirasia, Sikinos, Donousa • note that Amorgos *in full* is still possibly by trading in some rest days • the pontoon in Alopronia port is installed only in the main charter season.
Tinos Stavros on Donousa 44,
Stavros Kalantos 19,
Katapola Anafi port 40,
Anafi Vlichada 17,
Vlichada Thirasia 10,
Thirasia Alopronia 19,
Alopronia Despotiko 21 NM.
These routes feature at least 3 superb nightly anchorages • up to 4 rest/excursion days • lunch (or night) anchorages: Drima-Antikeros; all around Irakleia; Glaronisi; Pori on Pano Koufonisi; Dendro and Roussa on Donousa; Kalotiri and Gramvousa on Amorgos; Azala or Moutsouna on Naxos.

P	3 weeks Paros – Paros	View
Day	Port	NM
1	Parikia on Paros
2	Faros on Sifnos	22
3	Livadi on Serifos	19
4	"	–
5	Kamares on Sifnos	12
6	Psathi on Kimolos	14
7	Manolonisi on Polyaigos	2
8	Adamas on Milos	15
9	"	–
10	Kleftiko on Milos	16
11	Karavostasi on Folegandros	33
12	Vlichada on Santorini	29
13	"	–
14	Nikolaos on Thirasia	10
15	Alopronia on Sikinos	19
16	Ios port	7
17	"	–
18	Fikiada on Sifnos	31
19	Despotiko	16
20	Naoussa on Paros	28
21	Parikia on Paros	11
		284

Yacht charters: Route P South West Cyclades 3 weeks sailing itinerary — **P – South West Cyclades** with three options:

In **navy blue** the main & ideal route to reach Santorini (Thira + Thirasia) • 4 nightly anchorages • 4 rest/excursion days
The **red** legs bring you to some gems of the **Argolic Gulf**.
You can cross from Sifnos (or Serifos) to **Kyparissi** 81 NM, preferably plan a stop at **Ierakas**, to **⛬ Monemvasia** and then back to the Cyclades to Adamas 69 NM • 3 – 4 nightly anchorages • 3 – 4 rest/excursion days • **dolphins** almost guaranteed.
The **fuchsia** route proposes an easier second half that includes the Lesser Cyclades:
Day 11 Karavostasi
Day 12 "
Day 13 Alopronia 11
Day 14 Tris Klises 14
Day 15 Koufonisi 19
Day 16 Myrsini 8
Day 17 Naxos port 20
Day 18 "
Day 19 Naoussa 9
Day 20 "
Day 21 Parikia on Paros 11
**Total 225 NM** • 3 nightly anchorages • 5 rest/excursion days.
These routes, so far from Athens, are mostly off the beaten track • upon learning that the Alopronia pontoon isn't installed you can relocate to Ios port • the **Meltemi** can wreck havoc in these waters.
Anchorages to consider: Vathy on Folegandros; Ag Georgios on Sikinos; Ammoura on Polyaigos; Akrotiri and Kameni on Santorini; Vathi and Kastro on Sifnos; Strongyli islet west of Despotiko; and along the **fuchsia** route aim for Kato Koufonisi, Glaronisi, Drima-Antikeros, Alimia, which are all in the Lesser Cyclades.

Winds

Depths

Shore excursions

Ioulis, Polais (Kea)
Kastri (Syros)
Zagora (Andros)
Villages and dovecotes (Tinos)
Delos
Chora (Serifos)
Apollonia, Kastro, Ag Andreas Akropolis (Sifnos)
Marmara, Parikia museum (Paros)
Kastro, cave (Antiparos)
Sanctuary (Despotiko)
Demeter temple, Flerio, Cave of Zas (Naxos)
Trypiti, Chora (Milos)
Chora (Folegandros)
Palaiokastro, Skarkos, Chora (Ios)
Hozoviotissa, Aegiali villages (Amorgos)
Chora, Monastery Panagia Kalamiotissa (Anafi)
Akrotiri, Thirasia, Oia, Fira museum (Santorini)

Aegean itineraries 1 – 3 months

By popular demand an itinerary for one to three months in the whole of the 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, and most options in charter fleets.

Therefore, starting in Athens – likely Alimos marina – and after spending about 10 – 14 days in the Saronic and Argolic gulfs cross via Hydra to Kea or Kythnos en start exploring the open waters of the Aegean Sea.

Highlights in the Cyclades are Sifnos, Paros, Naxos & the Lesser Cyclades, Amorgos, Santorini, Milos and Folegandros. This will be a further 2 weeks: for instance Sifnos, Anafi, Santorini and Amorgos are worth more than one day.

Cross towards the Dodecanese from Astypalea via Kasos, Karpathos to Rhodes, Chalki, 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 Eastern 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:

South coast of the Peloponnese around the notorious Cape Maleas, worth an extra week at least;
Include Crete from Thira;
From Chios to Lesbos into the Northern Sporades, Limnos, Chalkidiki and Thasos;
Through the Corinth Canal via the Corinth Gulf and Patras Gulf into the Ionian Sea;
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 base of Paros. Furthermore, the ports of Syros, Mykonos, Milos and Santorini increasingly serve as useful secondary bases for yacht charters as well.
Frequent domestic flights, ferries and hydrofoils connect these islands with Athens Airport and Pireaus Port.

Unsorted tips

Athens (Alimos) Paros (Paroikia) is the most sensible oneway within the Cyclades, see one-way routes A, B, C and D. Note that this direction is greatly preferred, otherwise you would be sailing against the prevailing northerlies. In a 3-week scenario consider ending in Kos, see one-way route E, or Rhodes.
During the Meltemi season you should count on high seas and high winds (for a few days); it is therefore preferential to sail early or late in the charter season, see when to sail in Greece.
The island of Mykonos is now an overpriced magnet to the vulgarians, only useful to start / end your yacht charter holidays, or for the excellent guided excursions to Delos. Interestingly, Mykonos was previously known as the gay destination, since the 1960s, and well throughout the 1970s and 1980s.
Besides the main charter bases of Alimos Kalamaki Athens and Lavrion / Olympic marina, there are charter catamarans / sailing boats out of Paros: Parikia, Piso Livadi, Naoussa and to a lesser degree out of Ermoupoli or Tourlos.
My top 10 anchorages:
- Tris Klises on Ios island
- “Fjord bay” on Amorgos
- Kastro on Sifnos
- Poleis on Kea
- Manolonisi on Polyaigos
- “Sandbar bay” on Kythnos
- Chryssospilia on Folegandros
- Tsigrado on Milos
- Gamma cove on Despotiko
- Kameni volcano in Santorini caldera
In the 2 or 3-weeks scenarios it is possible to have 2 – 5 rest days / stopovers.
Plenty of the islands merit inland excursions, see the list above.
Moreover, most islands, notably Santorini, Tinos, Naxos, Paros, Ios, Amorgos, Anafi, Andros, Sifnos… have multiple worthwhile harbours and anchorages each.

Read more articles in my yachting guide.