East coast sailing – November 2021

Fake it til you make it.

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?

Verrazano-Narrows Bridge

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.

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Liberty x2

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.

Roosevelt Island Tram
Brooklyn and Manhattan Bridges
UN and Chrysler buildings
Ferries and Empire State Building

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.

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Mal de Debarquement syndrome


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.

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I was fine…..until suddenly I wasn’t

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.

Morning Sunshine

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.

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Working out the kinks


Got to the Marina just before dark. I had only seen a picture of Luke’s boat, Liberty. It was a beautiful 47ft sailboat from the late 80’s with wood trim and nice lines. We had some beers on the boat and crashed early.
The Captain showed up around nine the next morning. Luke had lashed the dinghy to the metal frame on the back of the boat trying to get it as high up off the water as possible for the trip south. I’m no expert, but it looked a little janky. The first thing Capt’n did was study this rig, silently, and for a long time. A really long time. “This is not going to work.” So we spent about half an hour securing it higher off the water with some limited success. But it looked good for now and we had to get going, so we fueled up and started heading south.
Out of the harbor we set sail and Liberty heeled over. Almost immediately the edge of the dinghy was hitting the water. Not too much, but clearly it would have to be addressed at some point, probably sooner rather than later. Not long after that the bilge alarm went off and didn’t shut up. Luke went below to investigate; pulling up floor boards to reveal a combination of diesel fuel and water. The bilge pump got it under control but we decided to pull into a harbor to fix the dinghy and investigate the leaks further. We had only been on the water about five hours. An inauspicious start.
We got the dinghy up almost another foot higher. It wasn’t going anywhere, but looked a little crazy with ropes like a spider web lashing it down. As I manually pumped the bilge free of the diesel mix, Capt’n was calm, “it is a nice boat just have to work out the issues. No surprise being it hasn’t been used much in the past five years. Plus it goes.” Luke seemed confident, although a little dismayed. I personally love boat Liberty; it is fun, fast and reeks of diesel. And as Captain says, it goes.

Diesel in the bilge
Dinghy after a lashing

We were off again. Set sail and blasted out of Portsmouth harbor, Maine as the sun set. The dinghy was now well out of the water. Got offshore and pointed south. The wind was westerly at 15 to 20 off the beam and in no time we were doing almost 9 knots. Then the manual bilge pump failed. Should I be worried? Wait! No! No!… I’m not worried about sh*t! I’m all in. Let’s go! Let’s go! It’s November in Maine and I’m freezing my butt off. North Carolina or Bust! It was on!

Portsmouth Harbor Lighthouse
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The Call

Tuesday Oct 26; Luke, one of my oldest friends called. “Buying a sail boat and need help sailing it from Maine to North Carolina. The sale isn’t final and I need to get insurance and an experienced Captain to help. That should happen in the next few days. I have to sail south before it starts to snow in Maine.” I started weighing the chance of this actually happening. Sounded like a lot of things needed to fall into place in a short time, so I was figuring maybe a 30% chance. Too low a possibility to concern Helen with it. She already has a lot on her plate, no need to unnecessarily have her think I might have to fly to Maine and sail down the Eastern Seaboard, at a moment’s notice.

Wednesday; Luke called back, “it’s on and we have leave to leave in a week.” Unfortunately that wasn’t going to work for me. We had long ago booked to stay in a cabin on the water that we wouldn’t be able to cancel. The timeline didn’t line up. I did mention the scheme to Helen, just in case, but she agreed there was no way it could work.

Another day, another call from Luke on Thursday. Change of plans. There was a good weather window in a few days. “We can get you back in time for your trip but you have to get here soon, so we can launch Monday at first light.”

We have a travel philosophy that if a unique opportunity comes up; just say yes. It has almost always worked out. This definitely fell into that category. I ran the new plan by Helen and I got the “are you kidding me?” look. But after some quick processing she also realized the potential of this endeavor; “you should go – it sounds like an amazing adventure, BUT – you better not miss our plan to go away.” I then told her I might have to fly at 6 am that Sunday. A sideways glance and a long pause, “Too early, take a Uber, I am not driving you.” She is not much of a morning person. I immediately texted Luke and his wife, Vanessa,”it’s on! but if I’m not back in time SHE WILL KILL US ALL!”

One other minor wrinkle. We were staying with friends for the next two nights, which meant I would get back home with only about 12 hours before my flight. In that time I still had to finish up some work, pack, tie up some other random things AND try to get some sleep before the alarm at 3 am.

Panic packing

Got the work done and started to pack. You would think by now I would be good at packing and getting ready for a trip quickly. I am not. Must be hereditary, my parents were terrible at packing for a trip. Finished at 11pm so my list of other things went by the wayside. The alarm went off but I still didn’t really have it together! Thankfully my lovely wife got up, got me on track and got me out the door.

Made it in plenty of time to the airport and once on the flight, I started to get my head around what I had signed up for. I was a little apprehensive. Me, Luke, H and Vanessa had taken the first two certifications of the American Sailing Association in the Bahamas almost fifteen years ago. Basically we learned how to sail a 30ft boat. Luke’s new boat is 47ft. And of course, I haven’t retained much of those courses from long ago; (nothing to do with the beautiful Bahamian rum of all shades that I imbibed during that trip,) and I haven’t sailed a boat since.

Now I’ve signed up to sail down the Atlantic Coast in November and I don’t really know what I am doing. Which side is port again? I didn’t want to be a liability, and this wasn’t going to be a leisurely cruise. We would be going non-stop day and night. It was going to be an all-out race to beat the weather.  

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