DODECANESE ISLANDS SAILING FROM KOS, GREECE | 2025

A detailed route within a custom layer on Google Maps

-1- [May 10th]
Kos

We visited this place back in 2019. It was fun and enjoyable — we traveled with four boats back then — here’s the article.
This time, we did a similar route, and it felt like everything was new again — the same places, but completely different emotions.
We used the charter company Istion — the same one we used in 2019. This time, we rented a catamaran Elba 45 (45 feet) instead of the Lagoon 39 (39 feet) we had last time.
The boat was relatively new — less than 5 years old (built in 2020).
All the sailing systems worked fine, but on the last day, a section of the interior paneling came loose on the screws due to the waves. It’s clear that this is a charter fleet — things aren’t built to last forever.
Istion clearly feels the competition and provides good service with lots of nice touches — like a complimentary bottle of olive oil and a bunch of colorful brochures about the company and other destinations — hoping we’ll come back again.
Over the past five years, there’s also been more competition — Archon is catching up fast in the same marina, with the first two piers now filled with their boats.

-2 - [May 11th]
Kalymnos (Vlychadia)

We decided to head north right away — even though there was a north wind (blowing against us).
The idea was to sail as far upwind as possible during the first two days, and then spend the remaining days sailing downwind quickly.

Our first stop and swim were at Vlychadia Bay.

It’s located slightly away from the main port (Kalymnos Port) — there were only four mooring buoys, which made the experience feel unique. It felt like we were there all by ourselves.

We listened to music from our DJ Alena and drank Aperol — the vacation had begun.
Soon after, the remaining free buoys were taken. We even tried to help another boat pick up a buoy (they only had 2–3 people on board), but then we had to rescue ourselves when our engine stalled.

Eventually, we managed to get the engine running again and went ashore to a restaurant — many ordered Greek salad, and we tried wild fried fish (very tasty, though not cheap).

- 3- [May 12]
Leros (Lakki marina)

The next day we sailed even farther north along the western coast of Kalymnos toward the port of Leros. On the way, we stopped for a swim near Emporios Beach. The island sheltered us from the wind, so the conditions were perfect — crystal-clear blue water and almost no breeze.

We quickly made a light Greek salad and opened a bottle of cold white wine. Everyone’s faces lit up — this was what a real holiday felt like.

As midday approached, it was time to cover everyone in sunscreen so no one would get burned. Although we had regular sunscreen, Vera’s bright-colored surfer creams stole everyone’s attention. Ilya even started painting on his face and torso with it, as if it weren’t real sunscreen at all. Later he spent a long time trying to wash it off =)
Vera explored the bay on the SUP — definitely worth bringing it along. You can cover quite a lot of distance that way without getting tired.

Later we made our way to Lakki Bay, took a short walk around the area, and spent the evening aboard the catamaran over dinner. At dawn we would set off back again — the journey ahead was a long one.

-4- [May 13]
Nisyros

We quickly reached our northernmost point, Lakki, and from there our route turned south — we were determined to sail to one of the most unique places in Greece: the island of Symi.

In a single day, we planned to leave our starting point on Kos and make our way to the beautiful island of Nisyros.

We set off at dawn, while it was still dark. There’s a special kind of magic in those early hours — when everything is still asleep, and we quietly slip out of the marina, already anticipating a beautiful day ahead. After our morning coffee, we captured a sunrise photoshoot.

Along the way, we considered stopping at the thermal springs of Kos and even managed to drop anchor. But gusts of wind were coming from every direction. The crew tested the SUP board, and some still made it to the baths. Dania bravely ferried two girls to shore and back from the anchorage.

After a short stop, we continued south toward Nisyros.

The island itself is almost perfectly round, with a circular road and several volcanoes that are still gently smoking. But the best part? Renting a buggy and racing around the island with the wind in your face. It turned out to be the perfect decision — we rented three vehicles and set off early the next morning.
Even the fact that two out of three cars had manual transmission didn’t slow us down — we adapted quickly, and soon dust was flying from beneath our wheels as we sped along the narrow mountain roads.

-5- [May 14]
Tilos

We spent the entire morning riding around in our buggies, in no hurry at all to continue the journey.

Meanwhile, the wind kept picking up, and we had to leave the bay sooner than planned to make our way to the next island — Tilos.

After a quick lunch and returning the vehicles, we finally decided to head back out to sea. The charter company from Kos managed to get us in touch with the harbor master on Tilos and confirmed we could sail there.

We practically “flew” across in under two hours, with the wind still pushing us from behind. But a surprise was waiting for us at the marina — there were no available spots.
We were only allowed to moor at the outer pontoon, where the ferry usually docks, and it was quite deep. We had to drop anchor three times before it finally held, but in the end, we managed.

The dock itself was concrete and not very convenient. At one point, we dropped a mooring line and it got tangled in the propeller. A diver came to check everything, even though we were sure we had cleared it ourselves. Honestly, that was reassuring — the company really looks after their boats and doesn’t take risks.

The funny part is that the harbor master himself helped us moor, but our boat wasn’t exactly designed for that kind of outer pontoon, so it wasn’t easy. We also had to stretch the anchor line properly to avoid being pushed into the dock by the wind.
I didn’t even go ashore, although the others managed to go for a walk and even a run.
Early the next morning, we set off for the final — and most beautiful — destination of our journey: Symi.

-6- [May 15]
Symi - anchorage

St. George Bay on Symi is one of those places that doesn’t feel entirely real until you’re actually there. Towering cliffs rise almost vertically from the water, enclosing a small, perfectly blue bay that you can only reach by boat. There’s no road, no beach bars, no signs of everyday life — just rock, sea, and silence.

We dropped anchor for a couple of hours, which turned out to be exactly the right amount of time. The water was impossibly clear, shifting between deep blue and bright turquoise, and the scale of the cliffs made everything feel small and still. It’s the kind of place where you don’t rush — you just float, look around, and take it in.
There’s not much to do here, and that’s the whole point. St. George Bay isn’t a destination you visit for activities — it’s one you remember for the feeling.

-7- [May 15 - night]
Symi

This was the most anticipated stop of the entire journey. I had sailed in this archipelago six years ago, but never made it to the island back then. This time, bad weather was approaching the next day — but with a favorable wind for the return — so we decided to go for it anyway. And it was absolutely the right call.

The island turned out to be невероятно beautiful and surprisingly quiet — just like the bay we had visited an hour earlier. It had everything: a harbor right in the heart of the town, easy mooring on buoys, very few tourists, and houses climbing along the cliffs all around.

We definitely had to work for the views — the climb up was steep and sweaty — but the photos were worth it.

Back on board, we settled onto the roof of the catamaran and talked late into the night. It felt like we had the whole place to ourselves, and no one wanted the trip to end — especially knowing we’d be heading back to the marina the next day.

At some point, someone suggested taking a group photo in our matching t-shirts with the catamaran in the background — and everyone happily went along with it.

-8- [May 16]
Coming back to Kos

The journey back started very early — calm, quiet, and almost windless. But as soon as we cleared the island, the wind began to build, steadily growing into a strong breeze. At some point, we realized there wasn’t a single boat around us, and it was a clear sign we should head straight back to the marina. The wind was no longer behind us — it was hitting from the side, howling, and people kept coming up to the helm asking if everything was under control.

By the time we arrived, the marina staff were already waiting for us — at least six people helping with the docking. It wasn’t easy in those conditions, with strong winds and the catamaran’s large windage, but we managed it.

And just like that, we had made it back — after visiting a truly incredible place.
There aren’t any photos from the final day, so I’ll share a few from the days before instead.