I didn’t need to look up, I knew they were watching us. Six people trying to maneuver a boat backwards into the open slip were bound to become a spectacle. They’d seen us coming. The giant logo running along our boom was a dead giveaway. And now, as the wind pushed us sideways towards their anchor lines, the crowd roared. They hurled insults, all in the local language, until one voice cut through the din – fucking amateurs! 

We’d been invited to sail the Greek islands about six months earlier. There would be seven of us. Three couples, and the east coast doctor who’d be our captain. He’d plan the route and we’d cook the meals, clean up and make sure there was wonder bread / cold cokes on hand at all times. It was a decent trade-off for the chance to see a country I’d had on my list for years. 

As the trip got closer, I reminisced. I’d sailed as a teenager, spending several weeks each summer on Blue Heaven. They were family trips and we were encouraged to learn from experience. I could read a nautical chart, secure the fenders and take the wheel. One year, we got caught in a storm. The wind was so strong, the anchor line snapped, and we spent the night trying to stay off the beach. I considered myself seasoned. 

These trips work as follows. Our captain books a boat through one of a few charters, usually Sunsail, or Moorings. I’m talking catamarans with four cabins, private or shared bathrooms and room for eight + one if you count the Hobbit Hole up front. They’re roomy. The route is typically seven to ten days, making it a perfect two-week vacation with some shore time on either end. Every person on board is assigned a job – in my case, opening and closing our waste valves, AKA the poo-pumper – and we all pitch in when it comes to cooking and general cleaning. It’s very civilized. 

Our first day on the water was short. We hit the grocery store, picked up our booze, packed everything into the holds and gathered for a somewhat serious safety meeting. Then, we were off. The motor to a secluded bay nearby was an easy introduction. I re-familiarized myself with the rigging, even tied a few knots. The ropes felt comfortable in my hands. It would all come back. I was sure of it. 

We didn’t actually raise the sails until we were out on the open water with some room to work. It takes timing and practice, of which we had neither. Instructions were called out as we crab-walked around the deck, sea legs yet to materialize. We weren’t fast, or particularly adept, but we got the gist. Enough that our captain figured we’d be able to navigate a marina without too much drama. He was wrong. 

At first sight, Hydra was the Greece we’d been imagining. Cream coloured buildings set into the hillside, culminating in a sawtooth façade at the water’s edge. Most were brick, squarely built with small windows and pops of red. In front, boats of every size jutted out from the boardwalk. Fishing vessels, small ferries and a mix of privately-owned yachts. There was only one open spot among them, and it looked snug. 

We circled. It was going to require a bit of finesse. Every boat docked nose out. We’d have to back in. The maneuver would happen like this – we’d pull forward, reverse the engines and drop the anchor. With fenders out, we’d keep backing up, tighten the rope and throw lines out to secure both the starboard and port sides. Theoretically sound. Dodgy when it comes to execution. 

The spot was narrow. A boat width, with a little wiggle room. Our issue was the wind. It would be pushing us sideways, requiring that we hit the ideal drift to engine ratio. The challenge was to sit light on the throttle until it pushed us almost into place, then loose the anchor and thread the needle. Too slow and we’d find ourselves pressing ham on the boat next door. 

I took my place at the bow, with the more experienced, and burly crew at the stern, ready to wedge a fender and possibly themselves between us a neighbour. The first run was little more than a test to see how fast we’d drift. The second, a serious try that resulted in some panicked running across the deck. Let’s not even talk about the third. And by the fourth attempt, the sailors around us were getting jittery. They leaned over the rails and catcalled. Sneering, pointing. I could feel my cheeks growing hotter. We took stock. Another attempt – or cut and run. I wanted to stay. We all did. But pride is a wily bitch. 

I’m sure they laughed. Raised glasses of ouzo to toast our departure. For us it was a case of nothing ventured, nothing gained. I’d like to believe that the experiences we chalked up over the rest of the trip were richer for it. At our next port of call, a restaurant owner jogged out to help us tie up, handing over a carafe of red wine as a gift. He set us a table under the stars that night, saganaki and squid at the ready. 

A day or two later, we walked through a deserted village, its inhabitants having already packed up and moved to the mainland for the winter months. I preferred it to the alternative. Throngs of visitors clogging the streets and taking selfies. A single coffee shop remained open, pink bougainvilleas overwhelming its tiny patio. We sat for a while and watched an old man put a final coat of blue paint on his shutters. He never looked up, obviously uninterested in the last of this year’s visitors. 

I celebrated a birthday that week. The start of a new decade. One that would see me embrace the label we got that day. As a writer, I’m a work in progress. Case in point, this last paragraph. I’ve been messing with it for three days. Ira Glass would tell me the truth — it’s trying to be good, it has potential, but it’s not there yet. I’m still crab-walking. And honestly, pretty fucking proud to be an amateur.