Adventure & Excitement, Greece

Sailing In Greece

I was standing outside the Spartakos Cafe at the port in Santorini, waiting to meet my tour group. I had signed up for a 7-day sailing cruise with the Intrepid tour group, with the plan being to spend a week bouncing around the Greek islands. But, with 8 minutes until our meeting time, I stood alone. I didn’t see anyone else loitering in that general area, nor did I see anyone advertising that they were with Intrepid.

I’d already double checked the departure date and meeting location to make sure that I was in the right place at the right time. I’ve missed flights before, much to my friends’ amusement. If I were to miss this boat, I’d never hear the end of it. I knew I was where I needed to be, so I resisted the urge to check the documents on my phone again.

Down the block, I saw a man standing with a clipboard with a sheet of white paper visible but at this distance, I couldn’t make out what it said. Possibly, he was the greeter for the intrepid group. I picked up my bag and walked in that direction. As I got closer, I could make out that he was a private driver who was waiting for his client, the sheet having the client’s name on it. I turned and went back to my post at the Spartakos Cafe. As I approached, a waiter from the cafe asked me if I was looking for the intrepid group.

Why yes, yes I am.

He motioned for me to follow him, and we went to the back of the cafe where I saw a group of eight people whose mannerisms suggested that they were just getting to know each other. I walked up to the group and asked, “Is this the intrepid group? “

A bunch of affirmative responses came back to me. I looked around the table and I didn’t see anyone who struck me as a captain. No confident slouch, no wise eyes that have experienced the world, no leathery tanned skin. I would have even settled for a T-shirt that said “Captain” on it. Finding no likely candidates, I asked, “Who’s in charge?“ Everyone looked at each other, and two people pointed at me and said, “You! ” and laughed. I grinned and said, “Then I think we’re in trouble!” I pulled up a chair and made myself comfortable. The nervous feeling in my stomach stepped down a notch now that I’d found my group.

Introductions were made all around, and I got eight names that I forgot just as fast as they were said. Miscellaneous small talk ensued, as I tried to gauge the vibe of my eight sailing companions.

A few minutes passed, and a well-tanned man in his late thirties walked into the cafe wearing a red Intrepid t-shirt. He was our greeter, at the very least, and clearly running on Greek time. With the captain’s appearance, the nervous feeling stepped down another notch or two, but didn’t entirely dissipate.

He introduced himself as Photis, the ship’s captain, and did a quick headcount at the table. He said, “Most of you are doing the 10-day trip, but who’s doing the 7-day trip?“. I raised my hand and looked around. No other hands went up. The captain said, “I’m not sure, but I think you may be the only one on that boat.“ I chuckled. He didn’t.

He went on to tell us the plan for the afternoon. We would hang out at the cafe for about an hour before boarding a ferry to Eos where the boats were docked. He looked at me and told me that I would meet my captain there. I nodded calmly even though my mind was racing. I knew that there were options to meet up with the boat later if your flight got in late or anything like that, so I assumed I’d meet the rest of my group later.

Getting off the ferry, we followed Photis down the ramp where he met a friend. They exchanged pleasantries in Greek and Photis pointed at me. The man introduced himself as Ilias and said he would be my captain. I waved goodbye to Photis and the rest of the group and I followed Ilias to our boat.

I asked him if anyone else would be joining us. He smiled and said no. I asked if he was serious. His smile grew wider as he said yes. I asked if this had ever happened before. He laughed and said no. Eventually we learned that another couple had signed up for the trip but they canceled just a few days prior. He had just found out that morning that I would be his only passenger. This scenario was so unusual that even the harbormaster, to whom he had to submit the passenger manifest, was confused.

As we walked, my head was spinning. I had signed up for a group sailing trip and somehow ended up with a private sailing charter around the Greek islands. When in my life would I ever have the opportunity to hire a private sailboat to cruise the Aegean around the Greek islands for a week? This was such an exceptional stroke of luck that I was still trying to make sense of it.

On the one hand, this was not what I expected nor was it what I signed up for. On the other hand, this was a very exciting twist. Now I just need to make the most of it, but what would that look like?