Sailing the Cyclades

Our crew of nine slowly coalesced over the course of a few days at a rented house in a suburb of southern Athens. On Saturday, we were leaving from a nearby port, where our boat was moored, waiting for the trip ahead. The days leading up to our departure were mostly taken up with gathering up the necessities for such a trip, which mostly consisted of a lot of alcohol, and a lot of food. At about 2pm on Saturday, all the members of our party were on the boat, and we pulled out from the port, heading southeast along the coast.

The boat.
Stocking up.
At least we didn’t run out.
The mess hall.

Our boat was a 45-foot Bavaria Yachts sloop, rented to the captains of our journey by an outfit in Greece that does such things. The captains we knew from our time on Utila; not only are they accomplished divers, but they are experienced yachtsmen too! In addition to piloting the vessel and teaching the rest of us on board how to sail, they handled a number of logistical tasks like composing a passenger manifest and handling several tomes of paperwork required for renting and sailing a boat in Greece. The rest of us ranged in sailing experience from essentially zero to having sailed a few times and knowing the basics, so the only two on board who could be trusted with the whole task were the captains.

Our itinerary was quite flexible, and nothing had really been planned more than a day or so in advance. Our only solid requirement was being on Santorini two weeks later. So, the Cyclades were our oyster, and we were free to take whichever path we chose, winds permitting. Citing our relatively late departure that afternoon, we settled on a spot some 20 nautical miles down the coast from Athens, still on the Greek mainland. We dropped anchor in a secluded little bay among several other sailboats, had some dinner on the boat, talked about our plans for the following day, and went to bed relatively early.

The bay at Apokrisi.

We decided to head straight to Kithnos the following morning, some 30 nautical miles southeast of our first anchorage. From the charts, the sand bar at Fikiada on the west coast of Kithnos looked like a nice place to anchor. Once we cleared the spit of land at the southeastern end of the Attic Peninsula, the meltemi picked up considerably, with gusts up to 40 knots. This made for a quick crossing, with some pretty serious heeling and lots of water splashing up on deck. The winds died down once we cleared the strait and got behind the cover of Kithnos a bit, so we fired up the engine and pulled into the secluded bay. It seems quite a few other boats had similar ideas, so there was not much space to drop anchor at a reasonable depth. We gave it a few tries before thinking better of the plan and heading east several hundred meters to the beach at Apokrisi. We found a lovely, secluded spot there with only a few other boats, within easy sight of the clamoring anchorage we had just left.

Fikiada sand bar.
A typical Aegean sunset.

After getting settled in, we headed to shore. Some of us swam, while others hopped in the dinghy. The sun was beating down with incredible intensity, but a few of us decided to go for a short hike out to the point southwest of Apokrisi. The views were beautiful, and the winds battered the barren, rocky terrain, no longer behind the protection of the island’s hilly northern tip. After a short while we headed back down to town, stopped at a taverna with some of the other crew to enjoy some appetizers and cold beers. It was here that we had our initial foray into the world of Greek fried eggplant, with which we were pretty taken. We prepared a similar dish on board virtually every night following. After a spell at the taverna, we headed back to the boat for dinner.

From a little hike we did near Apokrisi.
The boat at Kanala.

Our anchorage the next day was just on the other side of Kithnos, at the small town of Kanala. A direct sail from Apokrisi to Kanala is just about 17 nautical miles (and as the crow flies, over the center of the island, only about 8km), but our trip was quite a bit longer. The southbound sail from Apokrisi to the south end of Kithnos was rather uneventful, with a robust tailwind and sturdy swell rocking the boat, there was no need to jibe for the whole segment, and we were under power of the headsail only. Once we cleared the southern tip of Kithnos we bore northeast into the meltemi and brought up the mainsail. The wind was extremely strong, with gusts up to 60 knots, and the whole crew was on deck to help out. Some trouble with the mainsail led us out a bit farther than we’d like, and we ended up approaching the tiny island of Piperi before tacking to head back towards Kithnos. We tacked a few more times before the wind became legitimately dangerous, at which point we brought down the sails and motored the final several miles to our destination. Kanala proved to be a lovely town, and there was a nice bit of secluded bay that we could anchor in with only one other boat nearby.

The harbor at Kanala.
Kanala basketball court.

We again headed to shore and found ourselves at a beachside taverna to recharge some of our devices and fill up on water for washing. Several of us headed up the hill a short while later to collect some ice from the market in town. After dinner back on board the boat, we decided that we quite liked Kanala, and considering the relaxed time frame we were working with, we decided to spend the following day there as well. The following day was very laid back, and we spent our time variably hiking up in the hills around Kanala, relaxing on the boat, or running errands in town. As a few of us were taking care of some things around the boat, Oona noticed that the dinghy was no longer anywhere to be seen, and called our attention to that fact. We fixed our eyes towards the horizon in a panic and saw it drifting in the distance; apparently we hadn’t tied it up properly when we came back. The captain hurriedly threw on some fins and a mask and jumped in after it. It was a good several hundred meters from the boat at that point, but he was fortunately able to catch up to it before it hit the current in the blue and brought it back safe and sound.

Bro’in’ out in Kanala.
The dinghy in the distance.

We decided to leave for Siros early the following morning, and we set sails for the island at a little after 5am, bearing east southeast for the 25 mile crossing. We were witness to a stunning sunrise, with the glowing orb ascending through the mist as we heeled through the surf at an impressive clip. The winds were strong for the whole trip, so we arrived several hours earlier than we expected, well before noon. We pulled into the bay at Poseidonia and dropped anchor. Several of us went to shore to pick up supplies while a few others stayed on board to tend to some things on the boat. With the required provisions in hand, we were all back aboard the boat by mid afternoon. We concluded that we weren’t super into the place we were anchored at, and spotted a nice looking island called Didimi off the east coast of Siros on the charts. With quite a bit of daylight left on the clock, we decided to head there, a shortish trip of about 12 miles. We arrived to a fairytale of an island, with a beautiful and secluded bay of brilliant blue water with a small collection of huts and hammocks on the sandy beach several hundred meters away. Nobody lived there, so we supposed that people from neighboring Siros used it as a weekend getaway from time to time. There was not another boat in sight, so we dropped anchor in a wonderful spot, perfectly secluded from the northern winds. We had dinner and called it a night.


The next morning we concluded that this place was basically the best ever. We headed to shore to explore the island a bit, and made our way over to the lighthouse facing Ermoupoli, the main town on Siros across the channel. The lighthouse is abandoned, but wide open, so we climbed the steep spiral staircase all the way to the lookout on top, which afforded brilliant views of the waterways and islands all around us. With such a lovely spot all to ourselves we decided to spend another night here, and headed to Ermoupoli to get some food for a barbecue on the beach that night.

Looking at Siros from the lighthouse on Didimi.
From the top of the lighthouse on Didimi.
Didimi lighthouse.

After mooring in the bustling metropolis of Ermoupoli, we set out into the lovely old town in search of supplies. Things were pretty dead, as it was squarely within the hours of Mediterranean afternoon nap time, but we asked around for a butcher. A restaurant worker told us to head to the market and find a guy named Babi Salibaşi. We eventually came upon a butcher in the market and asked if he was our man, a quick nod confirmed our theory, and we stocked up on several kilos of various meats. After gathering the various necessities, including a bag of charcoal, a refill on our gas can for the dinghy and several dozen 5 liter water bottles for the onboard washing tanks, we set off towards Didimi again. Only this time, when we arrived to our previous digs, there were three (!) other boats where our anchorage was before, much to our displeasure. Nevertheless, we headed to shore to fire up the grill. We had a lovely night on the beach, and headed back to the boat for some sleep before the long trip southward the following day.

Our beach on Didimi.

Our next destination was a small cove between the islands of Despotiko and Antiparos, nearly 40 miles south of Didimi. The winds were pleasant, and typical for this time of year, coming from the north, so we cruised wing-on-wing for a portion of our trip. About a kilometer northwest of Despotiko the charts showed a small shoal at about 6 meters depth, so we decided to check it out. Sure enough, as we motored towards the spot marked on the map, a deep blue seafloor where there was open sea before lunged up at us. We dropped anchor at the edge of the small shoal, no more than 20 or 30 meters across, and jumped in to snorkel around a bit. The swell rocked us around a bit, but it was quite cool to see the ridge underneath the boat abruptly dropping off to the unimaginable depths on all sides. After a few minutes hanging out at the shoal we continued to our anchorage that night, among dozens of other boats in the cove between the two islands.

Oh yeah, we bought an inflatable unicorn too.

The next day we had a short trip up the east side of Antiparos to an anchorage just north of the village of Pounta on the island of Paros. There’s a dive shop in town, so we headed that way and booked a couple dives for the following day. After that, we headed back across the strait to the village of Antiparos to pick up some supplies and relax in town. Antiparos was a lovely little town, with ample cozy alleyways and some nice bars and restaurants.

A graveyard on Antiparos.

Those of us diving the next day took off early in the morning and hopped on the ferry across the short gap between Antiparos and Paros. We met up with the dive masters at the shop and headed down to the boat. The first dive was the wreck of the MS Express Samina a bit north of Paros. The ship went down in 2000, so it’s relatively new, and many of the things on board are still in decent condition. It’s beginning to cave in in some parts, and cars and trucks in the vehicle bay are visible, which is kind of a trip. We had a fairly long surface interval at the Spiridioni Rocks, and did some snorkeling and a short climb to the church atop the hill. The second dive was at “The Gates”, which are a series of underwater arches not far from the wreck, which was a pleasant dive, if fairly uninteresting.

A car in the MS Express Samina.
Swimming at Spiridioni Rocks.
Product placement.

After we returned from the dives, we headed back south to a peaceful little cove near the southern tip of Antiparos. There wasn’t a ton of space, so we dropped anchor and tethered the back end of the boat to some nearby rocks on the shore. The spot was lovely, but as we learned the next day it was quite a popular beach spot. We ended up spending two nights there as well, citing our somewhat late arrival after our dives.

Our next destination was the small island of Iraklia, a little over 20nmi east southeast. The sailing was quite pleasant that day, with a steady but entirely manageable 25 or so knots of wind for most of the day. After several hours in the blue, we rounded the northern tip of Iraklia in search of safe anchorage. Our first stop was Agios Georgios, a small town in a narrow bay just south of the cape at the north end of the island. There was a small petroleum carrier moored at the tiny dock, and not very much room for anchorage. We tried a few times, but couldn’t get lined up properly, and the town didn’t look that spectacular, so we decided to check out the next spot to the south, at Livadi beach. There was no shortage of space at Livadi, with only one or two other boats in the whole bay. We dropped anchor just as another boat was leaving, which happened to have its dinghy wedged against the bow as it was powering out of the bay. We called over to the captain to let him know what was going on. He was having trouble hearing so he pulled just a few meters from our stern, prompting a bit of sweat and readying of the controls. He was completely naked as we explained the situation with his dinghy.

Driving the boat.

After a few hours on shore for some of our crew, and some swimming around the boat for the rest, we headed off in hopes of finding a better anchorage at the next island, Schinousa. The twin masts of a huge schooner in the anchorage we were heading for were visible over the small islet just south of Schinousa, and as we made our way into the cove, all 53 meters of the beautiful ketch came into view. It turned out to be the Nirvana, belonging to Isak Andic, owner of the clothing chain Mango. We concluded that such a boat would be pretty cool to own. Instead, we conceded to anchor somewhat near it, in a secluded portion of the cove, but they set off an hour or so later. Our spot served as a decent place to sleep, but we didn’t visit the shore as there wasn’t much to be visited there, it seemed.


We set sail for the island of Amorgos early the next morning. We had our sights set on a nice-looking and quite remote inlet on the northeast coast of Amorgos, but had lingering doubts about its suitability as an anchorage due to its depth. Nevertheless, we thought we’d check it out in person, and headed that way at about 6am. The winds were very favorable, and we cruised at around 6 knots the whole morning until the mist-shrouded cliff faces of Amorgos came into view. The views of the island were quite spectacular, but the inlet we spotted on the charts proved to be too deep and too narrow for safe anchorage, not to mention a pretty serious swell being pushed in by the meltemi. Feeling slightly defeated, we turned around and headed for Ormos Egialis, a small town in a protected bay not too far down the coast from where we were. We dropped anchor in front of the sandy beach in town and everybody went to shore. Oona and Ian headed for a nearby cafe overlooking the beautiful, azure bay and had some beverages. Ian split off awhile later to wander up to Potamos, a small settlement several hundred meters up the hill, while Oona joined some of the other crew to run some errands in town, and generally soak up the vibe of the place. The town proved to be pretty amazing, with wonderful scenery but just enough of a tourist scene to maintain some great little cafes and bars. Most of the tourists we met were from Athens though, so it appears to be slightly off the general European tourist beat, for now at least.

The rocky cove on the north end of Amorgos.
A little beachside restaurant on Amorgos.

Meanwhile, Ian’s trip into the hills become longer and longer, civilization receding into the mists below. He followed a well-maintained stone path up into the mountains until he reached a ridge atop the island. Several centuries-old windmills sat in barely-recognizable disrepair among the evidence of a town that once flourished in the spot. The path led all the way to the chora, or the main settlement of the island, but given his unwise choice of footwear (flip flops), that goal sounded somewhat unattainable at another 15km south. Eventually, after 7 or so kilometers, he made it back down to the main road and hitchhiked with an older Polish couple back to Ormos Egialis where the crew again was complete at a beachside bar. The bar was hosting a fairly wild Greek party complete with dancing on tables and spraying people with a garden hose. The music kept up until 6am the next morning, when some of us were on deck preparing for the long journey to Santorini that day.

The whole crew on shore leave at Amorgos.

Our longest sail yet lay ahead, at more than 50nmi. We started our trip cruising down the north coast of Amorgos and rounding the cape towards the south, where we bore towards Anydros, a barren and uninhabited rock island in the blue between Amorgos and Santorini. There were a few attractive looking potential anchorages at Anydros where we thought we might drop anchor for a swim and some lunch, but there is virtually no information online or in print about this particular island, so it was a matter of checking it out ourselves. We had a powerful tailwind, so made quick work of the strait between Amorgos and Anydros. We tacked towards one of our identified spots just south of the northern cape on Anydros when something went terribly wrong with our mainsail; the furler sheared clean off the shaft attachment below, so we had no means of dropping the mainsail anymore. At this point we gathered that we would not be able to safely anchor at Anydros and instead continued towards Santorini, in hopes of being able to completely detach and drop the mainsail on the way. For what it’s worth, the island of Anydros did look like a suitable place to stop, with a reasonably secluded southern side, but it’s hard to tell if the depths would allow a medium sized yacht to anchor.

Having breakfast.
They didn’t catch anything.
Washing dishes off the back of the boat at night.

We made it to the southern coast of Santorini by afternoon, and were able to detach the mainsail, relying solely on the headsail for power. We ended up anchoring near the Red Beach for the night, and had a relaxed time swimming and basking in the sun, in spite of the hundreds of catamarans ferrying daytrippers to and fro. The following day we were set up with a buoy moorage just off the coast of Thirasia, opposite the maw of Santorini, by the owner of the rental company. As we approached the small settlement at the head of the bay, the depth meter still read 120 meters (!), and the deep blue below the ship confirmed that the bottom was a very long way down. We tied off with the buoy with the stern nearly touching the shore, the seafloor quickly dropping to invisible depths within just a few meters of the pathway running along the shore. It turned out to be a wonderful place to moor, as the whole crew jumped in to swim and free dive the moderate depths just below the ship and in front of the vertigo-inducing submarine cliff. The town was lovely as well, with a steep switchback pathway leading up the cliff face from the modest port settlement to the town proper above. It was mostly devoid of tourists as well, aside from the occasional daytripper from Santorini, so after sundown the place was mostly ours.

The bay in Thirasia.
The little town at the port of Thirasia.

It was here that the first crew rotation would be departing, and the second would pick up, with the captains and the second crew returning to Athens over the course of the next two weeks. So, we spent the day with the second crew as well, and had a big dinner at a beachside restaurant in the port with everybody, celebrating the birthday of one of the captains as well.

The following morning we bade farewell to our boatmates from the trip and headed to our hotel on Santorini. We had one night on the island before heading back to Athens and ultimately to Sri Lanka. We’re glad we didn’t book much more, as Santorini is a far cry from the isolated islands we had become accustomed to. Either way, we enjoyed our last night in Greece, and were settling back into the rhythm of being just the two of us again.

Leaving Thirasia by ferry.

All in all we had a fantastic time. It was amazing to have the level of freedom that a sailboat gives you, and we were able to visit some lovely islands. Learning how to sail better was a definite plus as well, and we feel a lot more comfortable manning the sails and controls of a decent-sized boat now. Our top spots from the trip were definitely Didimi (the small island just east of Siros/Ermoupoli) and Amorgos. We could certainly see ourselves spending some more time on Amorgos, visiting more of the towns, and maybe doing the whole length of the cross-island path.

Next up is a trip to Sri Lanka and India for a bit of business and holiday, so you can look forward to a short summary of that in the coming weeks.


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