The nighttime call of owls reverberated through the forest – a forest of 1,000 aluminium masts, like stands of pine trees stretching in all directions as far as you could see. Just looking at the vast rows of neatly organised boats induced a kind of vertigo as we arrived back at Cleopatra Marina on the west mainland coast of Greece.

Mega-boatyards like this one are becoming increasingly common and cruising Greece continues to swell in popularity each year. 

The sheer size of this dry-dock, combined with the factory-like efficiency of its staff launching vessels throughout the day – one every 20 minutes on average – was nipping at our backsides as we raced to tick off our spring, pre-launch checklist.

Non essential projects were quickly shuffled down the list while we focused on the most critical tasks, primarily replacing our old, underpowered 1980s anchor windlass.

For the last five years, my wife, Roxy, and I have been cruising aboard Sonder, our 1986 Cheoy Lee Pedrick 47, a cutter-rigged sloop. In 2020 we departed the Caribbean to cross the North Atlantic and eventually make our way into the Mediterranean.

Since then, we’ve explored some of the Med’s most remote gems, and also some of its charter hotspots – but perhaps none can match the popularity of the islands of Greece. The absolute flood of yachts departing on any given Saturday from ports like Lefkada and Piraeus had us a bit worried about our 2023 summer cruising season.

Could we still find ourselves quiet, remote anchorages, or be the lone yacht in an idyllic seaside harbour? Could we expect welcoming locals who don’t resent sailors’ overwhelming presence? Could we have an authentic travel experience? These questions lingered heavily in our minds as we launched Sonder in early May to begin our sailing season from Preveza on the Ionian Sea.

Late spring clouds pushed gentle easterly winds offshore as we sailed on a light starboard tack. Some 25 miles up the mainland coast we stopped overnight at an isolated bay just south-east of Parga, where the subtle movement of Sonder at anchor felt satisfying after the unnatural stillness of a long winter on the hard.

The next afternoon we arrived in Parga, a picture-perfect town directly opposite the very popular cruising destination of Paxos. Nestled on a saddle between a ruined Venetian hill fortress and steep foothills, Parga is vaguely reminiscent of the Amalfi coast.

The harbour, open to the occasional swell, lacks a large quay which discourages most charter boats from visiting, but by taking care not to foul your anchor on the commercial ferries’ anchor chains, two or three yachts can comfortably find space just off the small monastery with stunning views and easy town access.

Cruising Greece – Ionian adventures

This was how Sonder found herself the lone yacht in an idyllic Greek harbour right out of the gate. The waterfront of Parga is lined with alfresco restaurants, behind which lies a tangle of narrow alleyways and artist’s shops.

We stepped inside one and met a woodcarver named Stephanos, who skilfully shapes old felled olive wood and roots into bowls and sculptures. As we chatted and admired Stephanos’ work, the sky suddenly opened with a heavy downpour.

Being unforecast, we’d left some of Sonder’s hatches open, and were also slightly worried about our anchor dragging if this became a true squall. Stephanos quickly handed me his own jacket and I dashed back towards the dinghy through the narrow alleyways, dodging a calamity of al fresco diners also diving for shelter.

Once alongside, I could see Sonder’s anchor was holding well and, after I’d closed the hatches and mopped the floor, the squall abruptly subsided. When I returned ashore, Stephanos was already pouring shots of his homemade Tsipouro liquor for Roxy and I on the shop counter.

The next hours flew by as we shared stories about our shared love of the sea and carpentry – around 11pm we finally left, feeling warmly welcomed into the community in a way you rarely do as a tourist.

As May and June progressed and the Ionian became ever busier, we coalesced around the idea of sailing to the Cyclades in the Aegean Sea. While the busy Ionian islands have light afternoon breezes and many windless summer days, the Cyclades are known for the strong northerly Meltemi wind which can blow Force 7-8 for days at a time throughout the summer months.

Because of this we wanted to cruise the Cyclades islands from north to south, maximising our offwind sailing. This would mean taking the Corinth Canal route via the Gulf of Patras rather than sailing around the Peloponnese peninsula.

Besides this type of bigger-picture routing decision, we try to stay flexible about where we go and how long we stay. We find this leads to our most memorable cruising experiences.

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On a whim

An example was our decision to drop anchor on a whim at the small island of Atokos, en route to the Gulf of Patras. Atokos rises steeply out of the Ionian sea between Ithaca and the mainland.

On its south shore, surrounded by steep cliffs, is a tiny crescent cove almost out of sight from approaching boats. Inside is a sandy bottom anchorage just wide enough for three or four yachts to moor, stern tied to shore.

We arrived to find room beside an English-flagged yacht on our starboard and a Ukrainian one on our port.

It was late afternoon, but the sun, which in June was still high overhead, was already blocked by the sheer height and proximity of the cliff face towering over our yachts.

As the shadows crept further out into the bay, the sound of goats echoed off the canyon walls, but as soon as the sun had set the goats fell silent and no hum of a generator or buzz of a beach bar broke the silence.

I rarely have the opportunity while cruising, but that evening I decided to set up my electric keyboard in the cockpit to quietly play some music. Meanwhile our Ukrainian neighbours, a group of five friends, were busy gathering driftwood and building a fire on the beach.

Soon, someone shouted over in a thick Eastern European accent, “Volume up!”. So I proceeded to play a short set of some of my favourite jazz. The music seemed to reverberate against the cliffs like a natural amphitheatre, periodically mixed with applause from the beach.

Afterwards, Roxy and I paddled to the beach to meet our neighbours, who immediately invited us to join them, pressing glasses of wine in our hands. Three were Ukrainian while the other two were Russian. Though they’ve been friends for many years, their lives had been utterly upended by the recent war.

Through great difficulty they’d all managed to meet in Greece for their shared tradition of an annual charter sailing trip. Roxy and I were humbled listening to their stories of nights spent in bomb shelters, escaping from Russia when the draft loomed, and still remaining friends through it all.

Later, one of the Russians took out his acoustic guitar and, with the fire casting shadows against the cliff walls, they sang for us a few songs from their shared cultural upbringing in the Soviet Union. We felt so fortunate.

Onwards we pressed to the Corinth canal. The entrance to the Gulf of Patras is marked by a large suspension bridge spanning north-south over the narrows between mainland Greece and the Peloponnese peninsula. As a result, the wind tends to funnel through the channel, either eastwards or westwards.

The day we transited, steady westerlies of 15 knots pushed Sonder east at 6 knots on a deep broad reach. After passing under the bridge, the channel opens up into the Gulf.

Here I expected the funnelling effect of the wind to dissipate, but instead, the breeze built and Sonder steadily quickened her pace to 7.5 knots and then hull speed.

The wind kept steadily building with darkly bruised clouds accumulating above, around us choppy waves were stacking up with peaks cresting over.

Incrementally we reefed deeper until we had just a second reefed mainsail and scrap of genoa out, surfing in 35-knots plus, Sonder’s 22 tons gracefully surging ahead on the strongest wind we’d sailed in quite some time.

Under poseidon’s gaze

The Corinth Canal and Athens well behind us, we approached the high rocky promontory near the town of Sounion that marks the boundary between the protected waters of the Saronic Gulf and the much wilder Aegean Sea.

Without doubt, the ancient Greeks knew the importance of this junction and built a stunning temple to Poseidon, their sea god, upon these cliffs. Roxy and I glanced back at its white marble columns in hopes of his blessing as Sonder sailed out into the Kea passage.

The full June sun beat down on Sonder’s deck with a cloudless sky overhead as we set course for the ruins of Cartheae on the south east coast of Kea. Its rugged terrain, accessible by boat or a long hike, means few people make the trip to the temples, amphitheatre and Roman baths.

We dropped anchor on a sloping gravel bottom to explore the ruins and snorkel over the submerged rubble of an ancient stone quay. From the vantage of the ancient Greek temple we gazed down at Sonder, bobbing alone in the bay below.

Another, even more impressive, ancient site lies just five miles south west of Mykonos. Delos island is a UNESCO World Heritage Site and the ruins of this large ancient city could easily take a full day to explore.

While yachts cannot anchor on Delos, you can tie up directly to the quay by the ticket booth during the day, or anchor at the other small islands adjacent, as we did. There were so few other tourists arriving by ferry that as we explored the marble streets, it felt almost like a private tour.

Cyclades sleigh ride

By contrast to the quiet wandering of Delos, sailing into Mykonos was a shock to the system. No fewer than three cruise ships were in port, their multi-storey decks towering over the once-quaint fishing town. Day charter boats caused incessant wakes on the water while the honking car horns on shore felt jarring.

We glided into a small bay known as ‘Little Venice’, where white houses with colourfully painted trim are built right on the edge of the breakwater, their balconies overhanging the sea. Five whitewashed windmills line a ridge on the opposite side of the bay.

People steadily flowed down the narrow alleyways to catch a glimpse of this postcard scene, although truthfully, it was best viewed from our vantage point on the water.

In contrast to the quiet sunsets of the previous week, the water around us buzzed with activity. Boats full of tourists flew past like paparazzi, everyone snapping pictures. On shore, masses of people lined the breakwater to watch the sun slide below the horizon.

Then the tourists and day boats suddenly dispersed, leaving us to watch the lingering light cast a beautiful purple hue onto the whitewashed homes while a full moon rose right above Mykonos’s iconic windmills.

The next day, the infamous Meltemi fully arrived, with 30-plus knots blowing as we prepared to depart for Naoussa on the island of Paros, about 20 miles to the south. Uncomfortable 3ft short swells were running in the channel between Delos and Mykonos.

We unfurled just Sonder’s headsail keeping her as close to dead downwind as she would sail. This was the start of our much anticipated ‘Cycladic sleigh ride’, riding the Meltemi wind to zigzag down the Aegean island chain.

Soon we were out into open water and both the wind and sea moderated enabling perfect broad reaching conditions under full sails. The relentless heat was tempered by the Meltemi blowing cool air from the surface of the water.

Few other yachts were in sight and those we could see were presumed to be other cruisers since Paros is a long way from the nearest charter boat basin.

Naousa, with its large protected sand anchorage and tranquil village, is the cruisers’ antidote to Mykonos. The fishing harbour only has room for a dozen or so visiting boats tied onto the quay, but with a good dinghy you can zip into town from the expansive northern anchorage.

One of the final stops along our Meltemi sleigh ride south was inimitable Santorini. A partially-submerged active volcano – where you can actually sail into the caldera – Santorini is a truly unique island among the Cyclades chain. It’s also very popular with tourists and cruise ships, so we curtailed our expectations.

Hundreds of vessels of all sizes, from huge cruise ships to small day boats dotted the inland sea that is created by the caldera. We approached the opening from the north, having spent a long morning sailing almost 40 miles from Paros.

The Meltemi can be very strong as it squeezes between islands, but then mysteriously fizzle out in open water, so we spent most of the morning up on deck – reefing, then shaking reefs out, and scanning the horizon with binoculars looking for the ever changing wind line.

Inside the caldera, the top of the surrounding rim, over 1,000 feet in elevation, is covered with sprawling white-washed Cycladic style towns that rumble in a low din of activity.

From our sea level perspective they almost look like snow on a mountaintop high above. We felt removed from the chaos of it all while motor-sailing past. We had an anchorage in mind – one of the few protected from the Meltemi – on the southern tip of Santorini.

However, on our way was an opportunity to stop briefly at the active volcanic island of Nea Kameni in the centre of the caldera for a quick swim in the sulphur hot springs.

With Roxy on the bow and me on the helm, we piloted Sonder slowly through the narrow channel between the Kameni islands to a cove filled with deep-water private moorings for tourist day boats and, according to our chart, a shelf with a depth of about 20ft where we might drop our anchor.

The water, no longer a clear Aegean blue, had turned a milky green due to the influence of the sulphur springs nearby. While searching for the shelf and motoring at about 2 knots, I suddenly heard Roxy call back “Wait, how deep is it?”.

I picked my head up from the chart to look at our depth sounder and saw it reading 10ft and shoaling. Glancing overboard I could see a pale rocky bottom emerging rapidly from the milky depths. I threw the engine in full reverse, but was already too late.

Sonder’s keel let out a dull thud and we lurched forward. We’d grounded ourselves, for the first time on this side of the Atlantic, in unmarked shallows off Santorini.

From the bow, Roxy helped direct me to reverse Sonder off the rock shelf back into deeper water, where we quickly decided to just tie onto a dayboat mooring so we could dive the keel to inspect the damage.

Sonder’s encapsulated iron keel runs most of the length of the boat with a cut away for a skeg hung rudder. In other words, she’s built to brush off a small disaster like this and thankfully only had a few shallow gouges in the paint and barrier coat.

Charts are not to be trusted in this area and keeping sharp visual navigation is key.

After reviving ourselves with a quick swim, we gingerly navigated Sonder the rest of the way through the caldera and around the southern tip to Akrotiri Bay. The gentle sloping black sand beach of this coastline stands in stark contrast to the immensely deep caldera.

In fact, the lack of crowds and relaxed pace made it feel like an entirely different island. The nearby taverna, The Dolphins, has a dinghy dock free to use for cruisers while Akrotiri itself, an ancient Minoan city buried by ash from the violent eruption of Santorini around 1600BC, is walking distance from the anchorage.

Room for all

In the end, we need not have worried about Greece being overcrowded; with more than 6,000 islands, there’s space enough for everyone. If you want to plan for quieter waters, then cruising during the shoulder season can be helpful, but the area you choose will make a much bigger difference.

In the Aegean and Peloponnese, far from the mega charter basins (and where a week-long charter would require a long beat back) there were relatively fewer yachts. We found secluded anchorages and challenging sailing conditions that brought more rewards than we found on the Ionian side.

However, if tying up to town quays for lively nights out is more your style, that can be found in spades in the Ionian and Saronic Gulf. But our most memorable experiences came from moments of pure spontaneity… and shouldn’t all cruising feel like an adventure?

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