Sailing the Cyclades

August 22, 2016 - 5:06 am No Comments

We arrived at Santorini’s tiny port of Vlychada to meet our group for the sailing trip. Aside from me and Conrad, the group is entirely Australian. Four women in their 50’s traveling together and a couple in their 20’s. Our captain is Daisy, who is English and on her first sailing adventure with the company.

There are 2 cabins on board. The couple is taking one, Conrad and I have the other. Sleeping quarters are cramped, with Conrad and I sharing a thin mattress about the size of a double bed. The moment I first saw it reminded me of this scene from Planes, Trains & Automobiles. Conrad and I will sleeping head to toe, back to back to reduce the odds. This is in fact the opposite of a 69. It’s a 96.

Small Bed for Two

Our first afternoon, instead of sailing to another island, we annoyingly anchored just off the coast of Santorini. Everyone seemed to enjoy my geology lesson about volcanic Santorini, but it seemed like a wasted day to me and Conrad given that we had already spent a few days there.

Sunset in Akrotiri

The next day, we were off to explore the rest of the Cyclades, the name for the group of islands in the area. Instead of properly sailing, we had to motor through winds and pound into waves as we made our way north. On deck, we were constantly sprayed with cold water as we smashed into waves, and below deck, seasickness set in quickly. It was not a pleasant ride.

Buildings of Oia

Our first stop was Ios (EE-oss), a popular party destination and one of the most famous island stops on this trip. Conrad and I had wobbly legs for our first few hours off the boat, as if the whole island of Ios was rocking with us. We took a bus up to the old town of Chora and found it almost completely deserted. It seems that Greeks take the afternoon off, much like the Spanish do with their siestas. Then we plopped down on nearby Mylopotas beach for the rest of the day.

Cathedral of Ios

Blue Door, Orange Cat

Mylopotas Beach

Sunset on Mylopotas Beach

Back to the port for dinner with the group, where the friendly waiter treated us after the meal with a shot of rakomelo, Greece’s traditional brandy flavored with honey and cinnamon. Good stuff.


Conrad and I went back to the old town and found that it came alive with tourists and locals drinking and dancing. Seems that the nightlife out here doesn’t get going until about 1am. We did our own little bar crawl, including a stop at my first silent disco. Cool concept, but it’s all a bit weird. Taking off the headphones, the ambient singing and grunting from the crowd sounds like the worst party ever. At the end of the night, we walked back down to the boat, drunk and exhausted.

Jeff at Shush Bar

Next day, it was off to the tiny island of Irakleia (ee-RACK-lee-ah). As we arrived, a pair of dolphins frolicked around the boat.

Dolphin Spashes Around

Not a whole lot going on at Irakleia aside from a little cove beach and swimming. After a walk in the stifling heat and stagnant air through the tiny, sleepy port town of Agios Georgios, we collapsed at a semi-shaded outdoor cafe for a quick bite. I never liked canned iced tea, but when you’re hot and thirsty enough, Lipton Peach Iced Tea is amazing. We returned to the boat and killed the rest of the afternoon playing Hearts with Dan and Amy, the Australian couple on the boat with us.

Three Boats

In the evening, we found a bit of life at one of the rooftop bars. The waitresses fed us shots and danced with us.

Dancing in Iraklia

Then back to sea, where we determined that a watermelon does indeed float in the ocean (I won the bet).

Jeff Cranks

We’ve just arrived at Koufonisia (which seems to be pronounced koo-fuh-NEE-see). So far it’s beautiful, with a white sand beach filled with people and waters of impossible blue. I’m sitting at a cafe next to the marina, hot and sweaty and tired, with a can of Lipton Peach Iced Tea at my side. The heat really sucks it out of you.

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