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Sailing the Greek Cyclades

For the first leg of our Mediterranean vacation, we sailed a catamaran around the Cyclades islands in Greece. We started on Syros, scrapped our original route to Mykonos due to weather, and instead headed south. We sailed a few hours each day, dropped anchor at a new island each night, and poked around on shore or in kayaks.

This part of the trip was my dad‘s dream birthday vacation, and he earned it by doing most of the planning and legwork. We also celebrated my grandmother’s 90th birthday, which the crew loved. They proudly announced that she was the oldest person they’d ever sailed with.

Here are a few pictures and thoughts.


Our catamaran Anassa was 62 feet long and only a few years old. It was awesome, as was the crew. They knew their stuff, but they were still flexible and relaxed and lots of fun to hang out with. They knew interesting people and places everywhere we went, even when we quickly dropped off the beaten path.

Evidently Anassa was originally ordered by Roberto Cavalli, the designer, who turned it down at the last minute because he wanted something bigger. That explained a few surprising touches like the Italian tile in the bathrooms, luxurious if wholly unsuited to sailing.

The one odd part was being waited on. I know it’s the norm with this kind of sailing, but it just felt awkward. We made friends and spent time with the crew while they also served us food and drinks, wrangled our gear, and cleaned up after us. They were great, but next time I’d ask them to just sail the boat, and we’d all share in the chores.


We started with a ferry from Athens to Syros, which was our first glimpse of classic Greek island architecture: whitewashed stone, blue trim, built into the sides of cliffs, dotted with tiny patios, and steps everywhere. Cats everywhere too. Aww…

When we boarded the boat, our captain Jiorgos christened the voyage with his friend’s homemade dakos (?), a liqueur made with olives and juniper that tasted like a sweet gin. He pointed out a few of the other boats in the marina, including a big yacht owned by a friend of a friend who ran a shipping company. Then we were off!


Our first sail ended at Sifnos, where we docked next to another big yacht. We watched a crowd gather to wait for the ferry, and the commotion reminded me of old frontier towns. The stagecoach or train whistle stop was the big event of the day. Everyone stopped what they were doing and came to hear the news, get and send mail, restock with fresh goods, and see people off or welcome them back. Same with the ferry here.

After dinner, we wandered into the little harbor town to watch Greece play Germany in the Euro Cup. Jiorgos asked for a couple hours off to watch, and we said of course, but only if we can tag along! As expected, everything had stopped and the whole town packed into cafes and bars to cheer for Greece.


Appolonia is the main town in Sifnos.


Kimolos was the first island that felt truly secluded. We anchored at a quiet beach, and the water was turquoise, crystal clear, and mesmerizing.

During our sail, we asked Jiorgos a bit about his sailing experience. Among other things, he noted that catamarans were more stable and comfortable for passengers, of course, but they were less maneuverable and clumsier to sail than monohulls. We sympathized, but we appreciated the cat. We hadn’t gotten seasick yet!

Later, we eavesdropped on a Mayday call over the radio: man overboard. Jiorgos doubted anyone was close enough to help, and the boat would handle it themselves, but they were required to make the call. Someone did respond after a while, but by then they were in the clear.


Milos marked the high point of Jimmy Buffet style island sailing: self-sufficient, carefree, and idyllic.

We anchored near a catamaran captained by Jiorgos’s friend, who hopped in a skiff to greet us with a gift of fresh fish. Jiorgos and Vanessa immediately took it out to the beach to clean and fillet. No sooner had they arrived than Jiorgos looked down, darted his hand into the water, and came up with a little octopus! Vanessa proceeded to bash its brains out against a rock, grinning all the while, and a couple hours later we had grilled fish and braised octopus in an amazing tomato and herb sauce.

The next day, we kayaked and swam through some amazing sea caves. The only sign of humanity was a few scattered iron stakes, pounded into the rocks half a millenia ago by Aegean pirates.


Folegandros was yet another damn beautiful island with yet another damn beautiful cliffside town. We anchored underneath a restaurant carved into the hillside half a mile from the harbor town. They’d strung an extension cord the whole way for electricity, and brought in most of their supplies via dinghy. They grilled us octopus, calamari, fava beans, and vegetables, and we loved it all. The panoramic picture we took there is my favorite of the trip.


After so much blissful seclusion, Santorini was culture shock, since the tourists outnumber the residents as much as two or three to one at any given time.

The main towns of Oia and Fira have kept the classic cliffside Greek architecture, but inside they’re all hotels, restaurants, and boutiques. The contrast was striking.

The geography was striking too. Santorini used to be a nicely round island, but thousands of years ago a volcanic eruption sank much of the inland area, leaving only a C-shaped rim, a desolate caldera in the middle, and a bay whose ocean floor is riddled with unpredictable spikes and bottomless chasms. We literally don’t know how deep many of them are.

Santorini is also home to Akrotiri, the famously preserved ancient city known as the Pompeii of Greece. It’s cool for archaeologists, but as a tourist, it was a bit underwhelming. My mom claims it doesn’t hold a candle to Pompeii.


We bid farewell to our wonderful boat and crew in Santorini and ferried back to Athens. Beyond the expected sights, one notable feature was the ubiquitous graffiti. Locals claimed it’s exploded recently due to the protests over austerity and uncertainty about the country’s future.

Vanessa hung out in the city square one night, getting to know the local kids and drinking beer through a straw. When she asked if the police would care, she heard, “Don’t worry, there are no police in Greece.” Touché.


13 thoughts on “Sailing the Greek Cyclades

  1. Fast posting, Ryan! It was a great trip, and Dad was glad to have all of you celebrate his 60th year afloat with him….

  2. i heard something interesting on 99% Invisible this week: the blue and green doors (and windows) in greek and eastern european architecture weren’t just a nice aesthetic or tradition. they originally came about because they were thought to help keep away evil spirits. cool!

  3. It’s on our future list of vacations (I’m a huge planner) I’m curious if you’d share details on your planning with me. We are knee deep planning our bvi catamaran trip now. If its a hit. Then Greek will be next.

  4. Cool. I was going to ask about the sailing conditions, then I noticed you hired a crew. :-) What was the process of deciding where to sail and the time of year?

  5. good question! we didn’t try to optimize time of year much. i didn’t actually do a lot of the itinerary planning, but that didn’t matter, since we scrapped our original plan at the beginning due to weather and made a new one with an entirely different set of island.

  6. Excellent travel Logue. Another area someone can discover and relatively untouched from crowds is the small Cyclades. Perfect reviews from a company in the area is Greek water yachts

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