S2.3 - Sailing Through the Cyclades: April Adventures - Part 1
April 1: Departing for our Journey towards Syros – A Smooth Start
After a quick trash run in our dinghy, Ugh, Ryan and Charlie returned to find Emma and I prepping for our departure. The moment we untied the float lines from shore, we were surprised at how quickly Lucky Enough swung around—within minutes, we found ourselves on the other side of the inlet, thankfully still tethered to our 75 meters of chain! I guess there is a very good reason to have moored with lines astern.
We pulled up anchor and set sail for Syros, cruising along with 6-10 knots of wind.
The calm seas and stunning landscapes were a perfect start to the day!
April 3-5: Winds, Shakedown, Family Outing to Dilos
With winds shifting northerly, we set out in search of shelter, which gave us our first real shakedown of the season. We raised the Genoa, but as gusts hit 30 knots, we swapped it out for the Staysail and continued to rock our way to Rineia. What a bay!
Arriving early in the season meant we had the place practically to ourselves.
For a “family outing,” we took Ugh to explore the massive archaeological site of Dilos.
The island’s history and ruins were awe-inspiring—a reminder of just how ancient and incredible this part of the world is.
Ruins as far as the eye could see
Peek-a-boo Flowers
New life growing among ancient ruins
Timeless Columns
Through the Stone Walls
Ancient Temple Facade
Later, we made our way to Naxos Marina to refuel and spend (what we originally planned to be) one night. We pulled right into our mooring slip, met our Canadian neighbors, the Cousineaus", and their three daughters (soon to be four!) on their monohull “Jana”. After a bit of cleaning up, we headed out for a delicious meal at Taverna Naxos, where the server gave us excellent wine recommendations. Should you ever be in the area and would like to look them up, here is the list:
Peleponso (4 Fingers)AgiorgitikoXinomavroAssyrtiko
April 6-10: Waiting for Parts in Windy Naxos
Naxos is a beautiful town…
…but the marina (and it’s moored boats) certainly get rocked by the jet ferries coming and going.
Despite that, we loved it here—the friendly locals, scenic views, and amazing massages at Naxaki Massage were highlights. The therapist's intense, back-focused massages were much needed after our travels. I also got some solo time to explore the town, indulging in a quiet coffee and croissant.
With strong winds forecasted, we decided to stay put and wait for parts for our bow thruster to arrive via ferry. Naxos was the perfect spot to hunker down. One evening, we stumbled upon another amazing restaurant, Baco, where the food was simply divine, and the sunset views were unforgettable.
Sunset from Baco
We also started to truly understand the infamous Meltemi winds. Known locally as the ‘etesian’ winds, these strong, dry northern gusts blow through the Aegean all summer long, often arriving without warning. The winds hit 35-45 knots during our stay, reminding us just how unpredictable these particular winds can be.
Hang on to your hat!!
It was also time to say goodbye to Emma and Charlie, who had been a tremendous help onboard. While we enjoyed having the extra hands, Ryan and I were looking forward to sailing as a duo again, alternating between solo time and having crew for short stints.
Ryan returning to Lucky Enough on "Scoot"
April 10: A Sporty Departure and Tangled Prop
We left Naxos on a breezy, sporty morning, sailing downwind with ease until we suddenly felt a bad vibration under the boat. Ryan grabbed the GoPro, and sure enough, we’d snagged a line on the propeller. Unable to do anything at the moment, we shut off the port engine, hoisted the Genoa, and sailed our way to Paros Island.
Anchored at Faragas near the beach.
Ryan, ever the adventurer, donned his scuba gear and dove down to cut the line from the prop.
We then spent a sunny afternoon on the patio, enjoying beers and soaking up the Aegean breeze. That night, we treated ourselves to delicious lamb burgers stuffed with cheese and binge-watched “Baby Reindeer” on Netflix.
Cheers and Good Night
April 11: Changing Plans and Finding the Perfect Bay
Due to the great reviews on Navily, we originally planned to anchor at Saint George Beach between Antiparos and Despotiko, but strong winds forced us to rethink.
After scouting several potential spots, we found a beautiful, sheltered bay in the Despotiko Islet to drop anchor for lunch, but the winds were too strong to enjoy the scenery outside. After checking forecasts and discussing options, we decided to keep moving south.
Lunch Break
It was another “sporty” eight-mile sail, with swells and winds that made for an exciting ride. But our perseverance paid off when we discovered the quiet little fishing village of Faros on Sifnos Island.
Faros is a peaceful, untouched corner on the Island of Sifnos. It’s hard to believe it was once the main port of the island! Now, it’s a tranquil haven, far from the bustling ferry traffic that passes through Kamares. We’re thrilled to have found this gem and can’t wait to explore more!
April 12 - A Chilly Sail to Polyaigos
We enjoyed a nice downwind sail through Pyrgi Strait, heading toward the Island of Polyaigos. The anchorage at Polyaigos Paralia Kato Mirsini was beautiful, but the chilly winds made it hard to fully enjoy the outdoors. We took Ugh out briefly to check on the anchor, but that was the extent of our adventure for the day. Hopefully, warmer weather will arrive soon!
Red Skies at Night... Sailors Delight
April 13 - Magical Kleftiko Caves
The swells this morning were uncomfortable, so we decided to head to Milos. Passing Thiorichio Beach, we arrived at the magical Kleftiko Caves. We had the spot to ourselves for a while, until a French catamaran joined us. They anchored nearby but moved after realizing the wind was too much for the small space. We invited them for wine, but they didn’t join us. Instead, we swapped pictures and enjoyed the rest of the evening surrounded by stunning views.
April 14 - Relaxing Under the Sun
For the first time in a while, we were able to relax and enjoy the sun on our patio. Although still gusty, the winds weren’t as cold, so we took a couple of quick dips in the water to cool off. Later, we took Ugh out to get some close-ups of the caves, and I snapped tons of photos while Ryan captured some great drone footage. The scenery was absolutely magnificent—a perfect end to the day.
From the archaeological wonders of Dilos to the peaceful bays and majestic rock formations of the Greek Islands, these past 2 weeks have been a whirlwind of sailing, exploring, and unexpected surprises. The Meltemi winds are keeping us on our toes, but they’re also a part of what makes sailing in Greece so exhilarating.
We can’t wait to see what the next leg of our journey brings!