Sailing the Cyclades on S/Y Serenissima

May 10, 2025

From 3rd-7th May I was lucky enough to spend 4 nights on board S/Y Serenissima travelling from the tiny island of Poros to the Cyclades. The trip comprised one long sailing day of 5-6 hours and the remaining island hops were only a couple of hours each. This is a great itinerary for outside of the summer holidays, away from the crowds and in May and June typically avoids the strong Meltemi winds more consistently seen in July and August.

I was one of eight brokers on board this 10 berth Fountaine Pajoy 67. We were taken care of by three crew.


Captain Jordan – always greeted me with his famous smile and kept us up to speed with the day’s plans.

Chef Dimitris – an excellent chef and sommelier who would go the extra mile, even preparing food for us when we were not dining aboard; we each received a wrap to take with us to the airport.

Deck/Stew Vaios – quietly attentive is how I would describe Vaios and as skilled making cocktails as he was securing lines and detailing cabins.


Day 1

Poros to Serifos

We set sail from Poros and headed south towards Serifos. We were grateful that the wind had died down enough to go to the Cyclades. There was some residual swell which slowed our journey and meant that the red wine pairing at lunch was more of a red wine wearing. The pulled pork tacos were absolutely stand out though.

That evening we moored up in Serifos and headed ashore to Mpakakaki upon Jordan’s recommendation; a taverna with some more local style dishes such as beef cheeks.

Day 2

Serifos to Kythnos

Thankfully the waves had subsided by day 2 so we had a leisurely sail to Kolona Bay on Kythnos which has a rare sand spit dividing the bay into two halves. I took a quick dip in the very cold water before we headed to the beach for a picnic. Catered by all the chefs across the 7 boats in the Fam Trip Flotilla, Dimitris had prepared some slow cooked lamb which I was lucky to get. my hands on as it had all but gone by the time I arrived at the beach. The beach was also home to a hot spring which is about 30 degrees, a welcome change from the freezing sea I had experienced not long before.

Jordan informed us the higgledy piggledy walls that serve as land boundaries are not perfectly aligned as landowner’s historically tried to claim extra land by inching the stone walls slightly into their neighbouring pastures. This was met by the exact same retaliation from their neighbours.

That evening we headed into Kythnos port where a bus tour had been arranged to take us around the island and see all the picturesque villages. When we returned Dimitris had prepared a delicious dinner inspired by his mother, I think he was also trying to please me when he learned I was studying nutrition. It was hearty and soulful and unpretentious; we all loved it.

Finally feeling like we could let our hair down, there was a cocktail competition so we had to go and sample the other boat’s creations. We ventured as far as our neighbour Crazy Horse  before heading to Ad Astra  for a mysterious blue cocktail, music and dancing; I have a strong feeling we’ll be seeing a karaoke machine on board next year.

Day 3

Kythnos to Kea

We had an early departure from Kythnos and headed over to Kea where we had a brief wonder around the shops in the port before taking the bus up into the main town. Always one to follow the path 200m further than everybody else, we explored the quiet streets of Kea, climbing the cobbled, uneven stairs under a derelict house and a school that looks like it hasn’t been touched since COVID. Further curiosity led us out of the abandoned basketball court to enjoy an uninterrupted 270 degree view of the terraced hill sides of Kea. We were most struck that every inch of land had been worked at some point, reflective of the island’s agricultural past.

Buzzing from our discovery, we then trekked the opposite direction to find Kea’s infamous smiling lion sharing our recommended lookout to every broker we passed along the way.

We wended our way to the lion which we touched for good luck. Carved into stone in approximately 6BC it felt like we were following the path of many who had come before us. We stopped and soaked it all up, the sounds of the birds, the rustling of the wind. It felt like we could have been at any moment in time, remote from the hustle and bustle of every day life. We obviously snapped some photos on our smart phones though!

Whilst waiting for our bus to depart we witnessed a local brawl between two Greek men.

That evening was another cocktail competition, although we did think that Vaios’ were best, selfishly we kept that our little secret! There was a Greek night aboard Aether and music and dancing on Genny‘s flybridge.

Day 4

Kea to Lavrio via Sounion

There was an unsurprisingly slow start to our final day and a sense of sadness that we would be departing Serenissima and parting ways the next morning.

The day was spent in the bay of Sounion which is situated by the temple of Poseidon which sits high on the peninsula clifftop looking out to sea. It was enjoyable to have a slow afternoon, reading, swimming and soaking up the atmosphere before heading back to Lavrio for our final dinner.

Day 5

Homeward and so grateful that I got to participate in the Fam Trip again this year, it gives a total different perspective on the crews when seeing them in charter mode vs boat show mode.