For the past week I managed to work from a sailboat, mostly when not actually sailing. Both sailing for that long and working while on the move where two unique challenges for me. This work- trip wouldn’t become true if Automattic ( the company I work for ) didn’t have such a flexible work policy that allows employees to work remotely and async. While many companies are now allowing remote work ( Automattic is working fully remote since 2017 ), the key ingredient here is async. Async means that I can schedule my day in a way that fits both my personal and company goals. I notified my colleagues that I will be working with an intermittent connection and I will be splitting my day; working 4h before 09:00 ( the time we use to sail ) and 4h after 16:00 (the time we used to moor to a port). This way I managed to:

• work enough time to push the team sprint goals
• join most of zoom calls (all except 1)
• sail daily from one island to another and have a great time
• sadly the last day returning home was a little bit rough and I didn’t manage to work enough; I declared it AFK

The backstory

Back in December 2021 I did some courses to gain a Skipper diploma. I had been sailing while scouting but neither had I sailed big boats nor had an official diploma. After getting the required training I felt very comfortable with the bigger size and wanted to explore the possibilities; sailing longer and faster.

The trip

In May 2022, a friend of mine suggested that we rent a sailboat for 7 days and roam in the greek islands. So we, a crew of five, gathered and sailed from Lavrio to the western Cyclades ( Aegean Sea ). Our itinerary wasn’t set in stone as we had to take into account the weather and most importantly the wind. Eventually we managed to hop on – hop off in five different islands; Kythnos, Sifnos, Polyaigos, Kimolos, Serifos. Our covered distance was almost 180nm ( 1nm = 1852m).

Day 1 – Lavrio -> Kythnos

This was the worst day, not tough at all but three of us got sea sick. There were some strong sea currents and wind from our back which made the boat move in an irregular manner. We managed to moor in Kythnos port and swim. We visited Chora, Kythnos in the evening.

Day 2 – Staying to Kythnos

We decided to stay to Kythnos for one more day due to the bad weather as 6-7 beaufort would really put our skills to test. We visited Apokrousi beach in the morning and Dryopida village for dinner and then again to Chora for some drinks.

Day 3 – Kythnos -> Sifnos

The weather was a little bit calmer and enough for us to sail for a bigger leg. We decided to go to Sifnos, skipping Serifos. We reached Vathi in the afternoon. We visited Chora, Sifnos in the evening.

Day 4 – Sifnos -> Polyaigos -> Kimolos

Weather wasn’t great for sailing so most of our legs where motorboating. Distances where short enough for us to reach a beach in Polyaigos and then moor in Kimolos port. As always, we visited Chora, Kimolos.

Day 5 – Kimolos -> Serifos

Before sailing to Serifos, we visited Prassa, Kimolos; my favorite beach of the whole trip. Again, we visited Chora, Sifnos for dinner and then back to port for some drinks.

Day 6 – Serifos -> Kythnos

Before sailing to Kythnos, two crew members ( divers ) wanted to explore a ship wreck. Unfortunately there weren’t any signs of the diving spot. Nevertheless they got some great time diving and me doing SUP ( stand up padding ). We reached Kythnos by the evening ( my missed zoom call ) and off to Chora for dinner and drinks.

Day 7 – Kythnos -> Lavrio

Before sailing back to Lavrio, we went to Kolona a wonderful two-sided beach where the part of the land resembles a column ( kolona in greek ). After having some fun, we sailed to Lavrio. We got strong winds from a 30° angle making the inclination of the boat very challenging to handle. But this what I have signed up for and I totally enjoyed it!

The crew: Me, Kostis, Marios, Panos, Giannis