I realized I had been on the boat for a few days and hadn’t actually sailed yet. As we pulled out of NYC at dusk, I thought maybe now is the time; it would be cool sailing out of Manhattan. Great idea! Sailing for the first time in a decade, out of one of the busiest ports on the east coast at sunset. What could possibly go wrong?

We passed underneath the Verrazzano-Narrows Bridge, turned into the wind and got the sails up, before heading out of the channel to the open ocean. Initially I could easily see the channel markers, and track out our path on the radar screen as the light faded. No problem.
Luke and Capt’n immediately went down below to investigate and try to resolve the numerous mysteries of Sailboat Liberty. I was up on deck sailing alone; albeit nervously. I got this, I thought to myself reassuringly.
An enormous cargo ship passed to starboard. As I marveled at how big it was, an even bigger one passed to port. I didn’t even see that one until it was coming up right behind us. How did I miss something so massive?! It was full-on dark now.
My initial thought was to follow that container ship out. But I second-guessed myself and so tried to follow what I thought was the channel. I was having a hard time following it in the dark and felt I was drifting to the wrong side. The Captain came up as we passed a channel buoy to starboard, “You are a little close to that.” I probably had a sheepish look as I thought “Hell yes! I am close because I only just saw it!
The Captain cocked his head, contemplating that something wasn’t quite right here. At the same time we came to the same conclusion- I’ve sailed us totally out of the channel to port. I was outside of the channel buoys, on the completely wrong side of the channel. Basically It’s like I am driving on the breakdown lane on the wrong side of the highway, going against traffic. Thankfully no boats were around. Cap’t calmly walked over to the helm…”Let’s get us back on course.”
That was the last time I was behind the wheel, which was fair enough. I’m not sure ‘fake it til you make it’ applies to sailing. Whatever. I haven’t sunk us…yet, and I was loving it…. when someone else was sailing.

We sailed down Long Island Sound, passing Rikers Prison at noon, the whole island encircled with barbed wire, and then sailed onto the East River. Down past the UN, under the Roosevelt Island tram and both Manhattan and Brooklyn bridges.

It was quiet – only us and passenger ferries from the boroughs buzzing about on the water. Manhattan seemed almost calm from the water even though I knew there was a mass of humanity just beyond the shoreline. I imagined an office worker, high up in a skyscraper looking down on us, muttering to himself, “Wish I was on that boat”.

We hooked below Manhattan and refueled in New Jersey. I ran and grabbed a few more supplies, as we heard a storm was heading up the coast and we had to make it across Chesapeake Bay before it hit. We weren’t planning on stopping again, to achieve that goal.

We relaunched as the winter sunset turned the sky behind NYC orange, and posed for photos as we sailed past Statue of Liberty on Sailboat Liberty.

After 24 hours on the water, I got off the boat to go to the store for more supplies; most importantly, more Dramamine. I stopped by the marina bathroom on the way. It wasn’t long after I sat down that everything started rolling like I was still on the boat. I lost equilibrium and almost fell off the toilet. It felt like the ground was undulating. like an earthquake; Mal de Debarquement syndrome! You feel like you’re swaying and rocking even though you’re not, you can’t shake the feeling that you’re still on the boat.

I braced myself with my arms on the walls of the stall but It only got worse, I started to feel like I was now going to be sick. Not good! It would be a tough, unpleasant maneuver in this small toilet stall with multiple biological expulsions going on simultaneously. I did the math, the geometry just didn’t work.

Luckily things calmed down and the floor stopped moving enough for me to start to slowly walk to the store. It was fine when I was moving, but when I stopped things got weird.

I started wobbling around gathering supplies. It was early morning and the few people around kept their distance. Funnily enough, I don’t think it was because of the pandemic – I was definitely not looking my best after spending the night barfing off the deck of the boat. I had six layers of clothing on and with MDD syndrome I was stumbling down the aisles. It was only a matter of time before someone called the local authorities.

The night before I couldn’t wait to get off the boat. Now I couldn’t wait to get back to sailboat Liberty.

I took a preventative Dramamine before we launched out of Portsmouth, Maine. I haven’t been seasick for decades but my stomach over the years has gotten a bit more sensitive so I definitely haven’t been jumping on any roller coasters recently.

We got offshore and the wind was off the beam at almost 20 knots and the boat was bucking in the swell. It wasn’t too bad, a walk in the park for Luke and the Cap’n. But I seemed fine and didn’t want to show any weakness. I played it cool but I took a few ginger tablets over the afternoon and felt good all day.

I was getting ready for bed and was going to sleep in the front cabin. Luke warned that “The front cabin can be rough, the couch in the middle of the boat might be calmer.” I confidently responded “I’m fine, if I start to feel crap I’ll move.“

I laid down in the cabin and it was definitely bumpy but I fell asleep for a bit before the wind starting blowing harder and I woke up startled, bouncing around the bed. I spread out like a starfish to stay on top of the bed. But I still felt fine….until I suddenly wasn’t.

I scrambled out of bed and tried to get up on deck, fast. The floor was rocking haphazardly and I was pinballing around the cabin and not quickly getting anywhere near topside. It was like being in a tumble dryer. Time was ticking dangerously and my stomach was about to detonate. I lurched up the ladder and leaned over the deck rail and puked, just in the nick of time. Although if I’m completely honest, I basically leaned out as far as possible from the cockpit and puked on the deck; It was way too rough to go out on the deck and have the possibility of falling overboard!

I felt better, so went back down to grab a few more layers, a blanket and sleeping bag. I went back up to the cockpit and tucked in under the canopy to protect me from the cold, wind and spray. I wrapped the blanket around myself and stuffed myself into the sleeping bag.

Luke came up at one point to ask if I planned to sleep up there- Affirmative! No way am I going back down there.

I was the only one topside except for an occasional visit from the Captain. I faded off to sleep. Albeit a fitful sleep. I kept waking up slightly dazed at an ocean bleak and angry; a strong, blinding cold wind. The lights of Boston were barely visible as a glow on the horizon.

The boat was on autopilot, basically sailing itself. The large rudder wheel would spin as the autopilot constantly corrected course. Like some invisible entity was sailing the boat. Ghost ship.

I woke at dawn; with the sun rising above the dark ocean and below the gray sky. The sea and wind had finally calmed, slightly. I felt good, my stomach has also calmed and considering I had slept outside all night, I was warm, dry and rested. Mind you, first thing up that morning was a big glass of water and a large dose of Dramamine.