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Our Cyclades (Note: Greeks pronounce it 'Kick-lah-thez'; none of this 'sick-le-dees' stuff) cruising region stretches from Cap Sounion to The Dodecanese.  This is exciting sailing, and summer winds may sometimes force you to hole up for a day or three. There is an enormous variety of harbours and anchorages, but no full service marinas. Places to visit include some of the great sights (and sites) of Europe, and many good circular cruises.  The effects of tourism are mostly smart. The region is not overcrowded, and most sailboats are over 34ft. Night trips are not needed. Your summer cruise plans will be dominated by the meltemi, a persistent strong northerly wind. It'll take at least 4 weeks to see the highlights; add another 4 weeks if you really want to do a thorough job. Even that leaves something for next year.

Greece, and Boat regulations


It's usually easiest to go east through the northern islands, and west (the more difficult direction) through the southern islands (returning north along the Peloponnese coast, or through Kithnos and Kea). There are several strategies for working north in a sailboat: go in spring or autumn; run before the east Peloponnese southerlies; beat up through the more sheltered Dodecanese; pick a weather window; do early morning departures. Even so, there's a risk that a 20 mile bash to windward may be needed to get a charter boat back on time.   

The Islands

Working left to right, and zig-zagging top to bottom:

Cyclades Charts

Kea is a sparsely populated and rather bare island, whose only decent quayside at Vourkaki, in Agios Nikolaos, is often busy with boats in high season. There's a pleasant Hora 2nm up the hill, which only really comes to life in the peak season. Quayside tavernas cater for visiting boats, though I prefer the beach taverna 400m to the east.

Kithnos  is a quiet island, but a very good landfall from mainland Greece. There are many well sheltered and pleasant anchorages, ideal for a lunch time swim, within an hour's sail of Merika, the main port.

Serifos  is another quiet island, popular with yachts, but very little affected by tourism. From Livadhi, the main harbour, it's worth a visit to the Hora, one of the least spoilt such villages in the Cyclades. Take the bus, or a 40 minute walk.

Sifnos. The south coast has several beaches, developing into quiet resorts, which offer anchorages sheltered form the meltemi. But the most pleasant anchorage is the excellently sheltered Vathi, in the SW corner. It's a small village of nicely converted cottages, good beaches, a surprisingly large number of small tavernas and a very upmarket small hotel.  Lie to the quay if there's space. If not, anchor off, but consider two anchors in the meltemi, which produces some very strong gusts through the anchorage. Kamares, the main port, is adequate, but lacks character.

Milos  is centre of a group of once volcanic islands. It's really a small cruising ground in its own right, and a good jumping off point for a westward 60 nm hop to the Peloponese. The sheltered sailing area within Kimolos, Poliegos and Milos has a number of quiet, sandy, turquoise blue anchorages.  

  • Adhamas, the capital of Milos, is a town visited mainly by Greeks. Inside the L shaped quay pontoons are used by local craft. Visitors are (usually) charged for moorings tailed to the south side of the L-shaped quay, with water and electricity. Ferry wash is occasionally a problem.
  • The Mining Museum is just under 1km east around the bay from Adhamas quay. Top up your geological knowledge, listen to interviews with those who worked the mines, find what perlite does for plants, bentonite does for cats and pozzolan does for . . . it's a great visit.
  • Visit old Plaka, on the hill top. Catch a bus (or taxi, €6) then climb further up to the 'Kastro' for magnificent views. Time your visit for sunset — take a drink, and if the visibility is good, watch for the green flash. Stroll back down to the bus stop, dine at Archontoula (αρχοντουλα)  (a couple of metres toward the tiny village alleys) for its draft beer, interesting traditional menu, and good, discreet sound system playing a modern style of Greek music.
  • Anchor one lunch time just east of the SW corner of Milos - (map). The place is a bit prone to swell, but the coast is drilled with caves, dotted with islets, and surrounded by a 5m deep shelf of sand giving a brilliant turquoise anchorage. Explore by dinghy. A couple of shallow rocks will keep the lookout alert.

Syros is the crowded (35,000 pop) capital of the Cyclades, and ferry centre for the islands. The island is predominantly Greek, has few tourists, is busy, quite classy and not too expensive. There are two ports, many anchorages, a major shipyard and several minor repair and fit-out yards with a wide range of skills and facilities.  Frequent ferries to Athens/Piraeus and other islands.

  • Ermoupolis.  Ermoupolis has wonderful tavernas cluttered around the back alleys just east of the town square. Also search out 'Vlachos' ('BΛAΞOΣ') 50m west of the square off the market street. The quaysides are a great place for people watching, either from your boat or a quayside café. Good shopping and markets. Climb up to the monastery on top of the hill, wander round the tiny alleyways of the old city. In the main ferry port, ferry wash is a problem — moor well off the town quay
  • The well sheltered "marina" in the south of Ermoupolis harbour is physically complete but not operational. It's suitable for laying up afloat, about 4km from town centre, and a free shuttle bus runs between the nearby supermarket and town.
  • Two yards next to the industrial shipyard can haul out by wheeled sled or lift. With good chandlers nearby, layup ashore is possible, but strong local security arrangements make sleeping on the boat impossible.
  • Finikas.  Finikas is a favourite yacht stop, and has several resident yachts as well. There are many quiet day anchorages within an hour's sail. Barbalinas is a good restaurant here — it has a big takeaway trade with the locals. Try either the octopus or the (spicier!) kalamari stews.
  • Other Anchorages. There are many other bays around the island suitable for anchoring, some completely deserted - just turquoise water and a small stretch of sand.

Mykonos  is an international resort with simple architecture, very beautiful people (and they know it), expensive bars, wonderful sunset views and some very posh restaurants. Also, some more simple spots. Get lost in the beautiful maze which is the town, ignore the tourist tat for sale, balk at the prices in the art galleries, marvel at the polished turnout of the visitors, sit and recover with a cheap draught beer (takes a bit of searching). Yachts go to the "marina" quaysides 2nm north of the town (frequent buses). Lines tailed to the quay have been laid leading from a heavy ground chain. Lines are frequently chopped; and if using your own anchor, you're likely to snag the chains. Town harbour is reserved for ferries. Recover from sensory overload by anchoring in the quiet shelter of Rinia island another night, and visit the magnificent ruins of Delos.

Paros is well established as a tourist island even though it has no international airport. Between Paros and Andi-Paros there are a number of quiet anchorages.

  • Naoussa has a small harbour, often crowded, and is rather overwhelmed by tourist facilities. But there are many delightful anchorages around Naoussa bay and in coves just east facing Naxos.
  • Parikia is the main harbour and ferry port, with some typical Cyclades architecture. Go inside the harbour here if there's room, but at weekends it's full of charter boats. Mooring on the outside harbour wall is feasible, but leaves you exposed to the wash of some of the more careless ferries, so have plenty of chain out. Decent chandlers.

Naxos is a big island, with a lovely old main town (well sheltered harbour) which richly rewards some exploring. There are many tourists, who mainly live in the dense southern suburbs of the town, which have good sandy beaches. Places worth seeking out are:

  • Classic Greek food - try Lucullus, 'The Oldest Restaurant in Naxos — 1908'. Run by a pair of identical twins, it has a pretty street setting, and spotless kitchens. You'll find it by heading slightly left from the root of the quay and looking out for an archway labelled 'The Old Market'. Go in, turn left and search. You will be misled by a sign 'The Oldest Family Restaurant in Naxos — 1951' - ignore.
  • Mexican food, if you're dying for a change, try 'Café Picasso', Mexican. Serves tasty filet steak (or even an expensive buffalo filet steak!) as rare as you wish. It's just south of 'Plateia'. OK, to find Plateia go right from the yacht quay for about 400m, then turn left inland along 'Papavassilou', then first right after about 100m. 'Plateia' is a round-about,150m up the hill. Café Picasso is just beyond. Don't rush up to Picasso, or you'll miss two gems.
  • The Spice and Cheese Shop (on Papavassilou, about 100m beyond your right turn to Plateia) — an Aladdin's cave of spices, cheeses, olive oil and other local products. Wonderful smells.
  • The Beer House on Plateia — more types of draft beer than you can shake a mug at, and quite a good spot for a bit of people watching.  

Naxos-Paros Surrounds. The channel between Naxos and Paros creates a powerful funnel when the meltemi blows, with 35kt winds quite common — windsurfer's paradise, of course. Yottie's will have to reef their gin and tonics. Many islands, bays and anchorages surround the area, especially among the Minor Cyclades — a string of small, quiet islands just south, and it's quite possible to spend a week poking around and exploring afloat. , though working back north is a bit of a slog. This 44 minute video gives a fine picture of the dependence of small islands on their ferry services. It'll bring back many fond memories to those who have cruised the Cyclades. Jump through it if you're impatient!

Koufonisi (one of the Minor Cyclades), is a rather busy with tourism, but has many anchorages well sheltered from notherlies. In the main harbour, moor end on to the ferry quay (use laid lines if they've survived propeller attacks - otherwise, use an anchor trip line to escape the ground chain). Alternatively, squeeze through the narrow entrance to the tiny "marina" just SE of the main harbour.

Thyra (Santorini)  If you go here, you're going to have to beat northward again. It's worth it. But the hilltop towns of Thyra and Ia offer some of the most stunning views in the world outside the great mountain ranges. Moor in Vlikhada harbour off the southern coast; it's much easier to enter than some pilot books imply, though rather crammed with excursion catamarans. Winter storms often reduce the entrance draft to 1.5m, but this is regularly dredged to 2.5m for summer.  A glamorous restaurant/hotel down at harbour level usually accepts bookings for up-market evening meals. Two yacht friendly tavernas up the hill will arrange car hire. Tour the island vineyards and sample the wines (some very good). See the nautical museum, watch a sunset from Ia and allow yourself to be stunned by the quality of the villas with swimming pools and the apartments to rent along the crest of the crater. Ignore the tourists who'll clutter your path, and try not to trip over the honeymooners.

Ios.  Although a useful first stop when returning northward from Thyra, this is a tourist dense island whose otherwise charming Hora is now hidden by a thick veneer of shops, bars, kiosks, noise, booze and everything else people want tourists to buy. Since you're stuck with a visit to Ios, two recommendations should help. First, walk up the path to the Hora from the harbour (20 minutes) a little before sunset. Look out on your right before the top for the 'Ios Club', a civilised sunset bar. It's reached by turning right when you reach the road, and almost immediately turning right again past an 'Irish' pub. Lovely views, a quiet setting. Afterwards, seek out the 'Lord Byron Mezedhopolion' on the way to the Hora, which has interesting Greek food and, often, live rembetika music.

Levitha.  Right out to the east, this tiny island provides a very useful staging post traveling to or from the Dodecanese. The only resident family has laid about 10 moorings for visitors in their very well sheltered inlet, and mum will provide dinners for the crew.  If there's no moon, take a torch for the walk back from their house. There's nothing else!

Amorgos  is a popular yacht stop, with three or four tavernas ranked along the quay at Katapola to serve crews with a good profit margin. Much nicer is to take a half mile walk around to the head of the bay on the left, where "Karamel" serves better food at better prices. Take time to explore the Hora, one of the best preserved of such villages in the Cyclades. Monks welcome visitors to the monastery on the south coast. Both are accessible by bus or scooter, with a stiff path to climb to the monastery from the parking spot.

Anafi  is a place to pause in transit in settled weather en route from Astipalea in the Dodecanese, or to see the Hora. Perched just below the meltemi blasted ridge, the classic Cyclades buildings are authentically scruffy, with only thin evidence of tourism. Some pleasant tavernas and cafés look out from terraces to the south, and they're rather better than those on the sea front. The quay provides relatively little shelter except from the regular winds, so this is only a safe visit in settled weather.


  • Attractions: Many circular cruises; widely differing variety of islands; Cyclades architecture - visit each island's hora; not too crowded; un-intrusive port police.
  • Snags. Strong northerlies may interrupt your progress for a day or three. No full service marinas.
  • Ports of Entry.  Ermoupolis on Syros.
  • Layup or Wintering. Ermoupolis, Syros; on hards, or afloat in the (incomplete) marina. Otherwise, use Saronic and Athens area.
  • Transport. Seasonal charter flights connect UK to Mykonos, Ios and Thyra. Daily scheduled flights to Athens for these islands, as well as from Milos, Naxos, Paros and Syros. All islands regularly served by ferries to Piraeus and Syros
  • Boat Charter. Bareboat from Paros, Naxos, but best served from Athens and the Saronic


Reviewed May 2015


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