We’ll Probably Never Sail to Annapolis
Tuesday, October 12, 2021

Friday Morning - Picking up Jacob

9:00 a.m. on Friday. I’m driving to Ronald Reagan International Airport in Washington, D.C., to pick up Jacob, who is flying in from Cincinnati to spend the weekend with me on the water. It’s been almost three weeks since I’ve been on my boat. The last time I was on board, I was frantically packing all my cold and foul weather gear before my very sudden departure to Sweden to sail the Baltic and North Seas with the 59 North Crew. Upon returning from this extremely arduous trip (we sailed almost exclusively upwind in the roiling and freezing seas of Northern Europe for 10 days—and I was seasick for most of it), I was very, very happy that my good friends Lynn and Ingrid let me squat in their house, which is on SOLID LAND, for most of the week.

Jacob, one of my oldest friends from high school, also recently caught the sailing bug. He’s been there with me, either physically or digitally, for most of the big milestones in my nascent sailing journey. When I see him walking down the moving walkway towards me in Terminal C, I’m filled with gratitude and excitement that he’s flown in for the weekend. He’s pulling a little suitcase behind him that I know is probably filled not just with the clothes he needs for the weekend, but also with several tubes of sunscreen, seasickness medication, emergency radio gear, extra batteries, and who knows what other safety gear. Jacob is always the prepared one, and I love him for it.

Preparedness is a good thing out on the water, and Jacob’s attention to detail and what-could-go-wrong-and-how-do-we-deal-with-it mindset is especially welcome this weekend, as I’m feeling a little trepidatious after my trip from Stockholm to London. Sure, after sailing the North Sea, the Chesapeake Bay looks like one of those blow-up plastic pools, the Susquehanna river a garden hose draped over the side and filling it up. Perspectives scale, however, and my 31-foot Pearson looks kind of like a rubber duck when compared to ICEBEAR, the 59 Swan we sailed offshore. And being a part of a 9-person experienced crew is very different from being the skipper on your own boat. All this is to say, that despite my recent adventure abroad, and in fact, partially because of it, I have some nerves about returning to my home waters.

All the more so because the plan for the weekend is to hit a new milestone in our cruising careers: our first overnight outside of the marina. Until now, I’d been strictly a day sailor. Some of the days have been pretty long: I’d take the boat out of the slip early in the morning, tool around the bay all day, and bring her back just before nightfall. But until this point, the Pearson, under my ownership, has never spent a full night outside of slip E48 at Shipwright Marina. (Well, except for one night very early on that she slumbered while tied up to the end of the T-Dock because we ill-advisedly tried to go out in 30 knot winds and couldn’t safely get her back into the slip.) But this weekend, Jacob and I are planning to finally sail to Annapolis, the home of the U.S. Naval Academy and a sailing Mecca on the East Coast. Even though Annapolis is only about 25 nautical miles, an easy day trip, from Deale, Maryland, where my boat is docked, and even though I’ve attempted to sail there on several occasions, I’ve never quite managed it. The reasons for this continuously failed endeavor are many and varied, but the effect is the same: The simple trip to Annapolis has become something of my personal white whale, and this weekend, Jacob and I are going to finally change that.

Friday Afternoon - Pleasant Day on the Bay

We arrive at the boat around 10:00 a.m. on Friday morning, and I’m pleased to find that she’s still there, just as I left her, only with a bit more algal growth on the underside of the hull. We climb aboard and start dusting her off and preparing her for the weekend. Within minutes, we are more or less ready to set sail. We have all the food and supplies we need for this admittedly minor trip on board with us, and the sails are all rigged and ready to go. There is only one small thing stopping us from setting out this very minute and that is the wind. Namely, there is absolutely none of it. I’ve never seen “0 Kts” on the local weather station reading before, but there it is. Oh well, perfect day for a motorboat ride!

We are joined by my friend Rebekah and spend a beautiful, sunny, warm October day on the unusually placid bay. We put the sails up, just to show Rebekah, who has not been on a sailboat before, what they look like and how they, in theory, work. Without even bothering to setting an anchor, we just let the boat float on the perfectly calm waters and dive in and swim around her. This is my first time actually swimming in the bay all season—the thousands of jellyfish that normally plague the warm waters in the summer have finally receded and you can swim without fear of getting continuously stung by the so-called “sea nettles.” I swim continuous laps around the boat, seeing her for the first time from the perspective of the water. I’m struck by how good she looks, all 50 vertical feet of her, main sail still uselessly hoisted, floating there quietly. It occurs to me that this is the first time I’m seeing the boat in “third person,” if that makes any sense to you, and I’m filled with a sense of pride and joy in ownership. This feeling only increases later as I work in the galley, preparing lunch on the propane stove, and occasionally peek out the porthole at Jacob and Rebekah, who are both reclining in the inflatable kayak that is being dragged through the water behind the boat.

Me and Rebekah

Sun. Fun. Friends. Food. Water. Swimming. Boat. I watch, smiling, as some of my best friends in the world run and jump off the deck, swinging from the main halyard until they let go and splash into the water. I look down at my empty hands and am struck by a strange desire to be holding a refreshing Mexican beer. Suddenly, it clicks. “Oh my god, this is what it’s all about. This is why I bought a boat!”

The sunset

Sun-kissed and wrapped in towels, we motor back to the marina just as the sun is starting to set. Intensely satisfied with the afternoon, I find myself not even too nervous about docking, a very complicated process at my marina because of its insanely narrow fairways, tight slips, and stern-in-first policy. It only takes me two tries, an improvement on my usual… more than two.

Friday Evening - Planning the Trip

Jacob and I wave good-bye to Rebekah, hop in the kayak and paddle across the harbor to the waterfront restaurant where we plan our Annapolis trip over seafood and beer. According to our various weather apps, the wind will be coming out of the east all weekend, making it a fairly simple, and hopefully quick, affair to sail north on Saturday and then back south on Sunday. (For those of you reading who might not be as familiar with sailing, this might seem counter-intuitive, but sailing at 90 degrees to the wind, a “beam reach” in sailing terms, is usually the fastest point of sail.) We pick out a spot to moor once we arrive in Annapolis, check the Instagram of the Annapolis-based singer/songwriter that we both are in love with to see if she is playing any shows (she is not), finish our beers, and make our way back to our kayak, which we had tied up to the dinghy dock of the restaurant.

Now, Jacob has politely asked me not to include the following detail in this blog post, but out of a combined twinge of Schadenfreude and a narrative interest in the foreshadowing this anecdote represents for the rest of the weekend, I feel it must be told. We begin untying our kayak from the dinghy dock, in full view of the many bar and restaurant patrons, who, no doubt in our minds, had simply driven there in their cars that night (how boring) and were surely filled with envy and admiration at the sight of these two cool young men and their impressive means of muscle-powered water transport. Jacob, having just secured all of his valuables in a dry-bag that he brought along (always the prepared one), says to me: “They’re talking about us! Haha, how bad would it be if I slipped off the dock and fell in the water right now.” And before I’m even able to process, let alone reprimand him, for how bad of an idea it is to so obviously tempt the fates with such a statement, I watch as Jacob takes one awkward step into the unstable floating PVC plastic and, well, you can imagine the rest.

The Kayak docked at the restaurant

Minutes later, we’re silently paddling back across the pitch black harbor, trying to ignore the laughter emanating from the dockside restaurant behind us. Jacob, soaking wet in his jeans and sweater, is in the front of the kayak, and I, trying to keep my shoes out of the water beginning to pool in the cockpit, am in the back. We pull up to our dock and carefully (very carefully, this time) dismount, awkwardly climb up the ladder, and struggle to pull the kayak up onto the dock. It’s late now, and the marina dock is deserted. “At least nobody we knew saw that,” I say to Jacob, trying to cheer him up as he stands there, shivering, an extra 30 pounds of water-logged wool and denim clinging to his body. And just then, because it was my turn to tempt the fates with my statement, we hear footsteps and voices coming down the dock. We quickly move the kayak out of the way, and turn our headlamps off so as to not blind whoever is approaching. Before our eyes can even adjust to the dark and fully make out the approaching forms, I know who it has to be. My suspicion is unfortunately confirmed moments later when I hear a familiar voice that, even though it is dark, must be accompanied by a smile: “Well, well, well… are you guys finally sailing to Annapolis tomorrow?”

An Aside - Chris

Standing before me and cold, dripping Jacob is the family that lives on the boat across the dock from mine. The father, Chris, is one of the first people I made friends with at the marina. I met him one time when Jacob was visiting and Chris commented on Jacob’s “Ohio” shirt. It turned out that he and his family also lived in the Cleveland area before moving onto the boat, and Chris even went to the same middle school as me and Jacob. He and his wife, son, and daughter are getting ready to embark on a period of extended live-aboard cruising and are spending this season getting the boat ready at the marina before they head south in the winter. Apart from being friendly neighbors, Chris has been an immense and generous source of knowledge and support for this novice boat-owner. He’s loaned me tools, taught me knots, given me docking advice, invited me over for dinner with his family, and one time, when I was about to have a date come visit the boat and suddenly realized that I had not yet actually emptied the “black water” tank from the previous owner, he and his ten year old son helped me motor my boat to the pump-out station and clean it out. In short, without Chris, I would have been having a much rougher go of it during my first few months on board. I am extremely lucky to have him and his family around, and I do my best to show them how I’m learning and growing and making good on their advice and generosity.

But the one problem with Chris is that he always seems to show up at exactly the moment when I am fucking up the most. I’m happy that he helped me bleed out my fuel lines after I replaced the filters, but did he have to show up at exactly the moment I had spilled several cups of diesel all over the engine compartment? Or the time I thought I had killed my starter battery and was just sitting there, pressing the ignition over and over again and just listening to the click. Did Chris have to be running an errand right then? It really never fails. If I’m having a rough time getting my boat back in the slip, you’d better believe that Chris just happens to be standing on the dock at that moment, talking to somebody or hauling something to his boat, wryly smiling and giving a friendly wave to my incompetence. The time that my boat slept on the T-Dock overnight because we stupidly thought we could go out but couldn’t get back in? Guess who passed by with a wheelbarrow and a toothy, knowing grin right as we emerged from the bathroom, still pale from the experience of the emergency landing. “Where’s your boat, guys?”

So I am hardly surprised when it is Chris and his family who are themselves returning from a late dinner and happen across us standing there on Friday night, Jacob sopping wet, our kayak blocking the dock. Chris knows about all my failed attempts to sail to Annapolis and I’m sure that the image of the two of us standing there, wet and awkward, inspired confidence in my eventual completion of the endeavor.

Saturday Morning - Shifting Plans

We wake up early on Saturday, eager to put our plan into action. The first thing I hear when I open my eyes is the distinctive sound of halyards banging against masts. That means wind! I emerge from the companionway of the boat and step into the cockpit, my view slightly obscured by the half-suitcase worth of clothes that Jacob had hung out to dry after I had gone to sleep. It’s cloudy and slightly chilly, but the wind is definitely blowing from the east—a perfect day for sailing.

I’m making a coffee and Jacob is trying in vain to scrub the saltwater out of his jeans when I see a familiar face peeking into the cabin from the dock. It’s Chris’s ten-year-old son, Quinn, carrying a crab net and a bunch of string.

“Permission to come aboard? I want to show you guys something!”

Fifteen minutes later, and Jacob is fishing ten dollars out of his wallet to purchase a macramé knot contraption that Quinn had made for him. Quinn was only asking $5 for the custom knot, which he assured us would be a very useful tool to have aboard, but upon examining it myself, I remarked that it was of superior build quality, and, since Jacob was paying, clearly worth at least $10. Delighted at my brokerage assistance, Quinn decides to throw in a second knot so that I could have one too, free of charge. I thank him for his generosity, compliment his style of doing business, and send him on his way.

Quinn's Macramé

We start the Pearson’s engine and let it run for a few minutes to warm up the oil, check the batteries, and are about ready to set sail when Quinn comes back to the boat. “My friend and I caught a blue-shelled crab!” he yells to us, beckoning for us to come take a look. Jacob and I shrug to one another, admit that we haven’t actually seen a famous Maryland blue-shelled crab in person yet, and shut down the engine. We follow Quinn up the dock to a blue bucket, sitting at the foot of another boat, a Pearson 33—very similar to mine, but a little bigger and clearly much more equipped for cruising. “Do you know these people?” I ask hesitantly, unsure if I am about to trespass in some way by looking in the bucket. “Yeah,” he replies, “they are my friends. We’re going to St. Michaels with them today!” Satisfied enough, but still a little wary (Quinn is “friends” with every single person at the marina, but I don’t know what bucket- and crab-sharing agreements have been reached), I look in the bucket and marvel at the crab.

Soon, the owners of the boat come out and introduce themselves. They are another cruising family with Cleveland connections, have a school-aged daughter, and are clearly friendly with Chris’s family. Always eager to meet new people at the marina, Jacob and I tacitly agree to postpone our departure a few more minutes and hang out with Quinn and the Pearson 33 family for a while, playing with the crab and arguing over whether or not it’s large enough to keep. “Well I think you have to throw all the female ones back,” the woman says. “Did you check yet what kind of crab it is?”

“Not yet,” Quinn responds, slightly embarrassed, “but I’ve named him Jeffrey!”

“I’ll check it,” Chris says by way of greeting, as he walks up the dock and joins the party.

A few minutes later, the female crab is returned to the water, per Maryland state regulations, and the topic of conversation shifts to the plans for the day. The two families are planning to sail to St. Michaels, a popular cruising destination on the east side of the bay. I had heard it mentioned in conversation many times before and knew it to be a popular destination, but knew nothing else about it.

“I actually think we should sail south and then enter up through Broad Creek. There’s a a creek on the back side of town that we can anchor at,” Chris ventures, apparently proposing a change to the previously agreed upon plan. He unexpectedly looks at me and says “Jackson, you actually made me rethink our original plan last night when you mentioned the strong easterly wind and your plans for Annapolis today.” I felt my stomach flutter. Had Chris really made a sailing decision based on something that I had said? Even something as basic as “The wind is coming from the east tomorrow.” And had he really mentioned it publicly in a conversation with another sailing family? I nod sheepishly and quickly look over to Jacob, to see if he had also registered what just happened. I catch in his wide-eyed return look that he had. Wow.

St. Michaels

“You guys should come to St. Michaels!” Quinn yells, suddenly.

“Quinn, leave them alone,” his dad says. “Then they’ll really never make it to Annapolis!” he adds, but with a smile that seems to me to contain something else. Perhaps an invitation?

But the conversation shifts back to their trip and Jacob and I realize with a little embarrassment how long we’ve been standing there with the two families and that it’s time for us to leave, so we say goodbye to everyone, nice-to-meet-you to the Pearson family and begin to head back to our boat. Quinn follows us the whole way, practically walking on the backs of our feet, repeating one phrase over and over again in that way that only ten-year-old boys can:

“Come to St. Michaels, come to St. Michaels, come to St. Michaels!”

We tell him that we would like to, but we already have plans. We need to go to Annapolis. We don’t want to crash their trip. We are going to see a friend in Annapolis. We don’t even know the Pearson family that well. It’s too far for us. Jacob has a flight on Monday. We’ve never slept on an anchor before. We have to take baby steps. Sorry, but we can’t. We have to go to Annapolis. We already have picked out a mooring spot.

We tell him, and ourselves, all of these things as we are starting the engine, untying the docking lines, and begin motoring away from the dock. During this entire process, Quinn doesn’t relent. As we are moving away, Quinn is running along the dock parallel to us, until he comes to the end of the T-Dock, the very spot where we had an emergency landing only a few months prior.

“COME TO St. Michaels!!!” he yells with hands cupped around his mouth, in one final attempt to change our minds. We smile and turn around and wave good-bye. I steer the boat out of the harbor and we begin motoring out of the channel, heading east. We have about 20 minutes of motoring ahead of us before we are actually out on the Chesapeake. We are both standing there, not saying anything to one another, thinking.

“Well, we’re finally on our way to Annapolis,” I say. “Yep,” Jacob responds. More silence. Quinn’s pleas and Chris’s smile are clearly on both of our minds. A few minutes pass and I have Jacob take the helm while I look at the chart on my phone. It’s 10:00 a.m. I find the chart for St. Michaels and see Broad Creek and the back entrance to the town. It’s definitely further than Annapolis, and since it’s across the bay to the east, we’d be beating into the wind for most of the trip, but it looks like we should be able to get there by nightfall…

“Well, it’s not like Annapolis is going to go anywhere…”, I say.

“I think we should do it,” Jacob confirms.

We motor to the end of the channel, enter the bay, and since our bow is already pointing into the wind, immediately hoist the sails and set a course for St. Michaels.

Leaving the dock