Marblehead Meditations

Crew: Andrew, Lena, Sergey

Prologue

I call this blog entry a Meditation inspired by the book by Robert Pirsig “Zen and the Art of Motorcycle Maintenance” (recommended by Sergey on a gorgeous morning during our sailing adventure to Salem last year). The book describes the author’s motorcycle trip across the US. The narrative description is interspersed with what the author calls Chautauquas—for him, philosophical deliberations about the nature of “quality”. Which made me wonder—what would my Chautauquas be about? What do I focus on while sailing for hours uninterrupted except for a chart check or a sail trim here and there? And one word kept coming back: Communication. I realized a while back that of the many things that interest me in this world - underwater marine life, the immune system, writing, programming - communication is the common thread across all of them that interests me the most. So this time I decided, during the quiet time, to redirect my attention toward the true nature of Communication.

Five to ten knots with showers

The first overnight sail of the season was scheduled for the 16 and 17 of May: Sunday and Monday. That meant that I had all Saturday to prepare for the trip, which in turn meant that I was not going to have to prepare for it during the week. The result was that the weekend sprung up on me - it was not until Thursday the 14th that I realized that our overnight trip was coming up. I started getting excited - the sort of excitement that I had not felt since my previous overnight sail with this crew in September 2020.

Andrew had reserved the Eliza, one of the newest and nicest boats in the BSC’s “Cruising 35” fleet. The forecast was for 5-10 knot southwest winds with showers. The crew anticipated a slow day and prepared to make good use of the pre-packed rain gear.

The Eliza was waiting for us on her slip. Arriving at the BSC that Sunday morning and boarding our boat felt as natural as if our sailing streak had not been rudely interrupted by the Boston Winter for the previous 6 months.

Andrew undocked the Eliza smoothly, and pretty soon we were on our way to adventure. True to the forecast, the wind was no more than a breeze. It was actually blowing partially from behind us and partially from the Boston side of the inner harbor, which meant steady progress to the outer harbor with no heeling.

North or South

After passing Castle Island the wind decreased even more and with it, our speed. It also got warmer, which filled me with the desire to jump in the water. At the speed at which we were going, I could have easily jumped into the water, swam for a bit and gotten back on board. I didn’t though. The lull lasted only a few minutes but enough to have the crew earning for a lunch stop, possibly accompanied by some swimming. We first aimed for the public mooring balls next to Gallops Island, but they were missing their lines, which meant that we would have to anchor. The west side of Lovells Island had a good anchorage and the wind had slowed down again, which meant slow motion toward the island. I went down below to change into my swimsuit and told Andrew that I would swim to the island and meet him there. He agreed, but I chickened out. We were only a few meters away and yet with zero speed, not much was happening. In the distance, we could see what appeared to be rain falling at various locations across the harbor. After an uneventful anchoring, Sergey and I did swim for a bit. The water was very cold so for me it was less about swimming and more about jumping into the water and immediately getting out!


A small motor boat saw us and decided to follow our lead and anchor at the beach. Normally that would not bother us but instead of quietly enjoying their time on the island, the occupants decided to blast loud music from speakers on their boat and head over to the beach. Not very nice of them. Not very nice at all. As we enjoyed our lunch, the weather started changing around us. The sun disappeared behind the rain clouds. Waves rocked our boat and nearly spilled our drinks. And it started getting cold - cold enough, in fact, that it made Andrew and Sergey want to change into their foul weather gear. As we were putting the food away, it started to rain. The shower didn’t last long but it did make us want to go sail since the wind had definitely improved significantly!


We had planned to travel north for this overnight as the forecast had predicted SW winds for Sunday and NW winds for Monday, which meant that going north would not have us beating into the wind on either the trip north or the return. The reality that we observed, however, was a strong wind on Sunday blowing from the north. And if we couldn’t trust the forecast for Sunday, how much confidence should we have that the people at the National Weather Service had correctly forecasted the weather for the following Monday? None at all... We ended up travelling on a northeast heading to take advantage of the northerly winds and continued on to Nahant. The boat was heeling, we even had to shorten the jib to avoid heeling too much. In spite of the clear 10-15 knot wind which helped us make progress toward Nahant, the forecast continued to indicate southwest winds. We were of course loving the fact that we had good wind, but it was disturbing, to say the least, how wrong the forecast had been. Nahant came and went and it was still early so we kept going. After some deliberation, Sergey decided that Marblehead Harbor would likely be a much better / quieter anchorage for the night than Nahant given the northerly winds. We continued heading northeast, looking for our good old friend “red number four”. As for me, I kept looking out into the ocean hoping to spot a whale or two but it didn’t happen.

Marblehead Mooring

Arriving in Marblehead Harbor was uneventful. The wind continued to stubbornly blow from the north while the forecast stubbornly predicted southwest winds. I was puzzled by the lack of change in the forecast - isn’t that what weather stations are good for? Even windy.com, which is supposed to provide live weather station readings, was indicating SW winds. I stopped stressing about it and just enjoyed being on a sailboat with enough wind to get us to Marblehead Harbor. The inner harbor in Marblehead was somewhat protected from the north wind but not entirely, making the boat difficult to steer. There were also no anchorage spots, which meant that we would need to find ourselves a free mooring ball. The cruising guide suggested 3 yacht clubs renting mooring balls for transients. Two out of three didn’t answer the phone and the third told us that they were not taking transients due to COVID. Finally, we reached out to the Marblehead harbormaster, who told us to use our smartphones to pay for a mooring ball via dockwa.com and gave us a mooring ball number after that. As soon as we were moored, the rain caught up to us again. Perfect timing, it seemed.


After the rain softened, we decided to inflate the dinghy and row to shore. It was still raining slightly but the sun was making a re-appearance, which resulted in a stunning double rainbow over the harbor. The town of Marblehead was nice but it did not seem very large, with a park overlooking the harbor—an ideal place for panoramic pictures—and lots of cute, well taken care of stores that were still “closed for the winter”.


Dinner was served in the galley—Sergey’s specialty of spaghetti, tomato sauce and kosher sausages was delicious—accompanied by a bottle of the Pessimist wine that Andrew had brought. Even though it was cold, we did enjoy the night air for some time before tiredness took over, and we retreated to our sleeping bags.

Communication

I woke up at around 5.15. The sunrise was at 5.30. The sunrise is absolutely my favorite part of these overnights on the boat and I try very hard not to miss it! I pulled an arm out of the sleeping bag and damn, it was cold! I pulled myself out anyway, there was a sunrise to experience! With my shoes and jacket on, I opened the companionway and stepped onto the cockpit wrapped in my blue blanket, which I bring on board for these exact situations. The water was quiet. A few birds here and there. And a gorgeous orange-yellow-pink reflection on the water as the sun emerged above the horizon.

Meditation Interlude: The Sunday before had been too intense to think about communication so Monday was going to be the day. The first event that got me thinking about it was the distant sound of a bell coming from the town, which rang 6 times at 6AM. In this case, the communication was made up of a message—that at that moment it was 6AM—a communicator (not sure if a person or a computer nowadays) and an audience (i.e. the people who receive the communication). This was different from a 1:1 communication such as when I say “good morning” to Sergey because the bell’s audience is not specific: whereas I would probably not try to say “good morning” to Sergey if he was still asleep, the bell will (probably) still try to convey its message even if 100% of the people and animals within its hearing range were asleep. So that begs the question: if there’s no audience, is a message still a communication? I decided that no, if there’s no receiver of a message, communication does not happen.

The water was still too cold for swimming, so the crew prepared coffee/tea and oatmeal for breakfast, and just as we were getting ready for a second cup of coffee we ran out of propane. Our mooring neighbors had left and we needed to be on our way back to Boston as well since the wind forecast called for very weak 5 knot winds, which meant it would take us a while to get there. Nevertheless, we did have enough wind to cast off from the mooring ball at 7AM. We had failed to pump-out (again) much to Andrew’s dismay.

Leaving Marblehead Harbor

The Eliza made very good progress from Marblehead Harbor to Nahant - the wind was behind us, the sun was beaming and we were moving. And then, the wind died and our speed over ground was 0 knots. This was another excellent opportunity to think about communication.

Meditation Interlude: The topic this time was the communication of the marine animals swimming under our hull. What was on my mind was the question: when a whale sings, is it trying to communicate in the same way that I communicate “good morning” to Sergey and Andrew? Or is it communicating like the church bell? The whale’s language would be different and the message may be heard but not understood by us, which adds another element to the communication equation: language. If the message sender and receiver don’t use a language that is understood by both, the message is lost, so is it really a communication? Like us, whales don’t just use sound to communicate - body language is also key to the way they communicate. But of course, when they go about their business of fishing to feed themselves or to go to the surface to breathe, they need to move their body without any intent of communicating. So body motion may or may not constitute communication, which begs the question: does there have to be an intent to communicate in order for communication to occur? When a bigger fish is hunting a smaller fish, they try to be as still as they can until they can attack without being detected. When they approach their prey, they obviously don’t intend to communicate to the prey “I’m going to eat you”. And yet they do since the prey receives the message loud and clear and as a result will swim away. I decide that communication may or may not have an intent.

After a while the wind returned and we were moving again. It was quite early and we had made good progress toward Boston Harbor so we decided to stop for lunch somewhere. The wind had shifted and it was now blowing from the East - Great Brewster would protect us.

Swinging

Between the two Great Brewter’s drumlins we could see Boston Light. We dropped the mainsail and motored slowly toward the island. Every single time we do this, I always have the impression that we’re going to run aground because the island feels too close, but of course we never do. In these moments, whoever is steering the boat is paying close attention to the depth sounder to make sure that we’re not anchoring too far or too close.


We all went down to the galley to have our lunch, since the wind was making it very uncomfortable up in the cockpit. Normally, a good steady wind makes the boat point in the direction of the wind while anchored. But this time, an interesting phenomena was happening: we were swinging. Through the open companionway we could see our stern pointing in one direction for a while, then swinging and pointing in another direction for a while and then coming back to point at the original direction. It was making me a little seasick, to be honest.

Later, I understood why that was: to get to us, the wind had to go around the island’s northern drumlin - sometimes it was blowing stronger in between the two drumlins and our boat would point in that direction, other times it was stronger at the edge of the island, and so our boat would turn in that direction. We didn’t stay long in the swinging anchorage. Nobody swam this time, as far as I know (it was quite cold), but both Andrew and I did manage to take a short nap.

Soon enough we were on our way back to Boston. My last meditation was on the lighthouses and buoys in the harbor with which I had become very familiarized. Like the bell in Marblehead, they convey their message, whether or not someone is there to see and hear it. The first people who decided to mark certain locations such as “Sculpin Ledge” as dangerous—perhaps ancient mariners hoping they would return home safely—were communicating with other mariners with intent. Nowadays, the buoys that mark Sculpin Ledge are maintained by the coast guard, but the intent of the message they convey is the same even if the message sender changed. This begs the question—if the message stays the same but the sender and the receiver change, is it an instance of the same communication? I believe that it is. This belief helps me feel a special connection between us and all those other mariners who sailed these water, some of whom might have even lived hundreds of years ago.

Outer Brewster

Crew: Andrew, Lena, Sergey

The week had been long—particularly long because I had been working 11 hour days and putting in several hours over the previous weekend to get ready for a presentation on Wednesday. So a day sail on Saturday was very welcome as a way to recover my strength.

Our boat was the Camilla, a Beneteau 36.7—the same boat with the giant steering wheel that we had sailed earlier in the year to Provincetown. Andrew asked me to steer her out of the slip. “OK,” I said, “let’s do this”. With the wind directly ahead at us at this point, I did not face any issues getting out of the slip and turning her to starboard. Before raising the sails, Andrew asked me to build some intuition for driving her in reverse and taught me how to rotate her 180 degrees in place with the motor (if I remember correctly, the trick is wheel to starboard, a jolt of the motor in reverse, then wheel to port, followed by a jolt of the motor forward). In reality, the Camilla did not really like the reverse jolt but we did manage to rotate her in place. Kind of…


Then it was time to sail! There wasn’t a lot of wind, but we were going to try to sail anyway. With the mainsail raised, she sailed a bit but not a lot, so we unfurled the jib. The inner harbor had some spots with wind, but it was very spotty. We made slow progress toward Castle Island. Andrew wanted to visit an island. I looked at the chart and both Middle Brewster and Outer Brewster seemed to be able to provide protection from the south wind—not that the wind mattered much for anchoring at that point as there wasn’t any! The Brewsters and neighbouring islands are always fun places to visit—this same crew had visited Calf Island earlier in the year and we enjoyed it. Sergey really wanted to go to Outer Brewster, where he and Andrew had been before—Sergey’s favorite island in the harbor.


We would need to turn the motor on if we wanted to have time to do some island exploration. Sergey turned on the engine—which was fortunately not very noisy—and steered us toward South Channel. Andrew and I were navigating.

I was still thinking about how to guide Sergey through Hypocrite Channel when Andrew asked “where are we going to anchor”. He’s always 4 or 5 steps ahead of me. I immediately said, “we need the cruising guide!” (I remembered how I had tried to google for anchorage in Nahant and failed!), to which Andrew responded “we don’t have a cruising guide” (because this is a blog and not a vlog, you’re going to have to imagine me making the “epic fail sound” here).


I glanced at the chart, and there were a few places where we could anchor. I was looking for depths of 15-20 ft that didn’t get too shallow too fast. What I didn’t consider though was the wind direction. There was a little bit of wind inside the arrowhead-shaped body of water between Calf Island on one side, and Middle Brewster and Outer Brewster on the other. The wind was blowing from the east, strangely enough. We aimed for the region just right of Flying Place, i.e. the channel between Middle Brewster and Outer Brewster, in the hopes that we would be able to row to Outer Brewster, the island that Sergey really wanted to visit.

Just like last time when we had been here, the profusion of lobster traps made for a high anxiety inducing anchoring attempt. I understand that the fishermen have to make a living, but it’s a big ocean, they could drop their lobster traps further away from anchorage sites (and give the lobster a little bit of space to roam free without having to worry about a trap!). Anyway, we aborted the anchoring because we were too close to Middle Brewster, and the wind was not blowing us away from the island as we expected it would. There were really no good anchorage sites along the north coast of Outer Brewster so Andrew made the decision of going around the island and trying the anchorage by the south coast.


Here again there was a profusion of lobster traps. After a careful anchoring maneuver while not getting our propeller caught in lobster traps, we were able to drop the anchor and verify that it was secure. I looked over the life lines and saw dozens of tiny jellyfish in the water—I think they were Mnemiopsis—they looked very cool! They don’t sting and they glow blue-green when disturbed. It might’ve been fun to swim among them but neither of us was very sure about whether the jellyfishes were the stinging kind or not.

Jellyfish

After waiting a few minutes to make sure that the anchor was holding the boat, we opened up the lunch buffet! Homemade bread and hummus, compliments of captain Andrew, complemented with smoked salmon and cream cheese, compliments of helmsman Sergey and navigator Lena. Andrew brought some of that nice rosé wine with grapefruit juice that he often brings, which had the double advantage of being a delicious wine and not staining the deck like red wine tends to do.

Then, it was time to go explore Outer Brewster—we inflated the dinghy and off we went. Sergey had seen a gravel beach on the way over that would be a good place to beach our dinghy, so he guided us there. There was indeed a gravel beach next to an abandoned fortification—the only problem was that there didn’t seem to be a way into the rest of the island from here. After looking around we found some rocks to climb and a path forward.

The gravel beach that Sergey had seen

During World War II, Outer Brewster was part of a military reservation (thus the fortifications). Probably because of the low availability of freshwater (mostly from rainfall), the greatest biodiversity in the island is along the intertidal pools. As a side note—during my marine biology days, I learned that the reason why these pools are so diverse is because of the high availability of oxygen, which is very attractive for several underwater and bottom dwelling creatures, but it comes with the disadvantage that the pool can dry off or freeze, leading to a fierce struggle for survival that accelerates the emergence of biodiversity. The rock formation and the pools on the island reminded me of days spent collecting sea urchins from intertidal pools while the waves crashed on my cold and numb legs.

After going around the rocky shore, we found a way to climb to a trail. I was glad that I had decided to wear my jeans that day because the thorny plants were plenty (not sure what led the thorny plants on this island to thrive… or maybe they had been brought here for a purpose, perhaps related to its use by the military).

The Camilla and Boston Light

Sergey found a way into the barracks, which were pretty cool, and then he found the “dungeon” he was looking for—a T-shaped set of corridors that was long enough to be in complete darkness in certain places. We ended our Outer Brewster adventure by climbing to the roof of one of the barracks to admire the awesome view of the Boston Harbor Islands—we could see all of the Brewsters, plus Calf Island and Little Calf, Green Island and Roaring Bulls. We could also see Boston Light, the Graves Light and the city of Boston.





Our return to the Camilla was uneventful, and soon we were on our way back to Boston—contrary to what the forecast had predicted, the wind was coming from the west, not the south. Sergey was once again a helmsman, and I was a navigator—once we cleared Shag Rocks, the wind died, leaving me to wonder whether we should turn the engine on. Fortunately we didn’t have to, as the wind soon picked up again and we were flying toward the Narrows. With the east wind, I calculated, we would have to tack our way up President Roads. When we got there, however, Sergey noticed that he could steer close to the wind and point toward the line of red buoys marking the right side of the channel, which probably meant that the wind had shifted to a south south west direction. Hey, looked like we were going to make it without tacking after all. And we did! After a successful docking maneuver performed by Sergey, the crew lingered in the boat for a while and toasted to another successful day on the water.

It’s easy to get used to this life—knowing that sooner or later Andrew is going to ping me about an upcoming sail, and I’m going to do everything in my power to join him. However, as I witness the weather changing around me and the trees dressing up for Fall, and the inevitable “last day of the season” rapidly approaching, that feeling of “Mono no aware” or the transience of things becomes stronger and stronger. This time of year I often catch myself dreaming about travelling and settling in a place with warmer weather where I can sail year round. But I think I would not easily find anywhere else like Boston Harbor and Massachusetts Bay. In a way, it is the transience of the sailing weather in these parts that makes this a very special place to sail.

Salem Sailing

Crew: Andrew, Koby, Lena, Sergey

The Eliza

The Boston Sailing Center (BSC) had heard us and had felt our pain. Back when we were on the Anne on Martha’s Vineyard we had had significant “head” problems and left them several messages and emails asking for help. They were not able to help us at the time and as a result we lost a whole day of vacation doing work that none of us was equipped or motivated to do. So, to compensate us for our troubles, the BSC gave us a free 3 day cruise on one of their newest boats—the Eliza, a Jeanneau 349, a little sister of the Pura Vida, the Jeanneau 440 that we had sailed in the Spanish Virgin Islands back in January.


The original plan had been to cast off Friday morning, September 11th, and return on Sunday. However, we heard some bad news on Thursday: Sergey would not be able to make it on Friday and would have to join us on Saturday. That, combined with the forecast of NE winds of 15 to 20 kt with gusts up to 25 kt and seas 4 to 5 ft, made me wonder whether we should cancel the Friday sail and take off on Saturday morning. A quick call with the crew and we settled it—we would have the Shabbat dinner on the boat on Friday night (and potentially sleep there) but not cast off until Saturday morning.

You will do everything today

It was almost 6AM, and I could not sleep. The waves under the hull of the Eliza made for an uncomfortable night. “I’ll just get up,” I thought, “and wait for the sunrise.” One arm out of the sleeping bag and I lost all of my resolve—it was cold! I allowed myself to stay cozy inside the sleeping bag for another few minutes. Panic of missing the sunrise got me jumping out of the bed at 6.20AM and onto the bow to watch the sunrise over the airport.

It was better than I could have imagined—this was only my second time waking up on a boat in the sailing club, and the previous time the weather had been overcast so I had not seen the sunrise. Multiple cormorants perching on the pillings around the sailing center made for an entertaining show while the sun came up over East Boston. I wondered for a minute whether I might be happy living in a building by the seaport but as soon as I heard the roar of the first airplane lifting off at the airport I quickly realized—nope, not for me.


When Andrew arrived at around 8.45 I was in the cockpit reading my book when he said “Today I am just a passenger, you guys will do everything”. OK, this was new. First things first—we had to undock safely, so Sergey, Koby and I deliberated and decided that we would let the wind push us away from the dock. That worked well, and soon we were making our way to the middle of the inner harbor.

Then, it was time to raise the mainsail and unfurl the jib, which we did easily and without any drama after Sergey turned her into the wind (the perks of a newer boat are that her lines and sails are still new and glide up easily). We had good speed, perhaps 5 knots, and Koby was at the helm. We started feeling the 3-4ft waves upon passing Deer Island Light and venturing away from Boston Harbor and into Massachusetts Bay. At this point we had to make a decision about our route—with Andrew acting as a passenger only, Sergey and I had to put our heads together, look at the chart, consider the current wind and the wind forecast and make a decision. Since the wind was coming from the east, we could either go north or south. The forecast indicated that the wind would shift to the southeast, which would still work for either a return to Boston from the north (we would return on a beam reach) or the south (we would return on a run). Sergey made an executive decision to go north and attempt to make it to Gloucester before nightfall.


But before we ventured too far into North Channel that would take us there, we decided to reef the jib and the mainsail. The Eliza had the lines for the first and second main reef on the port and starboard sides of the mast, respectively. Without confirming which one we should be trimming, Koby and I started trimming the starboard reef line (second reef) before Sergey asked “are you sure you’re trimming the first reef?”. We weren’t. After clumsily fixing our mistake we were back in action and sailing at about 4 to 5 knots. It was my turn to navigate and plan our course to Nahant first, then Marblehead and finally—if we had enough light and wind—Gloucester!

Saying goodbye to Boston. For now...

Sea Sick

Maybe it was because I spent too much time staring at the chart, maybe it was because I had gone into the salon to grab my gloves, but at some point I started feeling sea-sick before we had even reached Nahant. Koby was also not feeling 100%, so the crew decided to stop in Nahant for lunch. Sergey asked if Nahant would be protected enough from the winds and the waves. A quick glance at the chart was all it took to realize that Nahant (bay) was too exposed to the east to make for a relaxed lunch. I had given up on Nahant at this point and was ready to keep going when Andrew had to intervene (the first time he did that day, he had been very disciplined so far letting me make navigation mistakes) and point out that there was another side to Nahant—Nahant Harbor.

Making good progress toward Nahant.

Aiming for Nahant Harbor was a no-brainer for Sergey and I after Andrew pointed that out—it was open to the west but since the winds and waves were coming from the east that day, it should be well protected. The next thing we would have to decide was whether to moor or anchor and where. My first instinct was to use my phone for a google search. Wrong instinct and unsuccessful search. Sergey went to the salon and came back with the cruising guide that Andrew always brings—aha! He learned that it was possible to anchor but that in order to do so we would need to call the harbormaster. As we were approaching the anchorage area, we saw a sailing boat drifting toward and getting tangled with a fishing vessel that was moored in the harbor. The fishing vessel had two outriggers sticking out of the sides which had caught their mainsail. Not a great position to be in. We briefly wondered if we should help them but it was unlikely that we could do a better job than their motor could, and we did NOT want to end up in the same situation. After some time they managed to untangle themselves and be on their way but, for me, it was a good reminder of the need to pay attention to the details but still be aware of the bigger picture when sailing in a confined space.

Andrew was at the helm, going around in circles while Sergey and I figured out how to operate the windlass since pushing the “down” button on the control didn’t do what it was supposed to do which was locking the chain and slowly letting it out. When we figured it out I shouted back “we can anchor”—I think I naively assumed that Andrew was going to take that as a hint to decide where to anchor but he just looked at me and reinforced his resolve: “You guys tell me what to do, I am not making any decisions today”. And we did.

Lunch was nice and relaxed. When it was over, there was some deliberation about inflating the dinghy and visiting Nahant. We ended up not doing it—which was a good thing too because we would not make it to Salem before the nightfall otherwise.

Winging it in Salem Sound

Either Sergey or Andrew (I can’t remember who) asked me to take the helm for cast off. Since the windlass would not work while the engine was off, we did not cast off under sail (although it would have been a good opportunity to do so otherwise). I asked the crew to raise the sails but something was off still. I could not sail very close to the wind—which was coming directly from where we needed to go—and tacked a couple of times to try to get out of Nahant Harbor and yet we were still stuck and tacking at 180 degree angles. Andrew said nothing, but I’m sure he was burning up inside. Still drowsy from seasickness, I handed the helm over to Sergey, and he quickly diagnosed the problem: both of our sails were still reefed even though the wind had slowed down! Which was a problem—what little wind that we had, we were not using. After shaking the reefs, we were able to travel much closer to the wind!


Our next milestone was the red buoy number 4 which marked the end of a shallow area by Marblehead neck. There was not a lot of navigation to be done between Nahant and our next milestone. Andrew showed me how to use parallel rulers to precisely determine our heading. Once we got to the red buoy number 4 which, as usual, magically appeared in the horizon exactly where it was supposed to be, we would have to make a decision about how to actually enter Salem Harbor.




We had two options: we could either take Marblehead Channel, which was clearly marked with lighted buoys or we could take the “shortcut” South Channel, which was more exciting (i.e. more narrow) and marked only with unlit buoys. Andrew, upon witnessing our deliberations, said “South Channel is tricky… like Woods Hole tricky”... Oops… that definitely raised all sorts of flags in my mind before he added “minus the currents”—I remembered all the planning that had gone into planning that woods hole crossing back in July and Sergey and I had done no planning whatsoever.

Andrew’s note. I did say so to make sure the crew paid attention in a tricky channel, but I didn’t mean to scare them off: I honestly misremembered that channel’s difficulty. It turned out to be nothing like Woods Hole (though honestly, Woods Hole itself also turned out to be not such a big deal). There were no side currents and related dangers in South Channel; the crew just had to carefully follow the buoys—which they did with flying colors!

It was getting close to nightfall so depending on how early we arrived at Marblehead Channel we would have to make a decision to either go through the safe (and long) route or go through the adventurous (and short) route. Furthermore, we had to consider the direction of the wind, particularly if it would force us to tack in the narrow South Channel (which we definitely did not want to do). Since the wind was still blowing from the east, and it was approximately 6PM when we approached Salem Sound (sunset was at 7PM)—we decided that we could make it through the short route! I felt brave—we were doing this!


Koby was at the helm and he steered us through the channel masterfully! Sergey had anchored in Salem Harbor before, so he knew where to go (Andrew also knew but he kept his professorial silence). In the distance we greeted the Fort Pickering lighthouse as we made our way to the massive mooring field in Salem Harbor ahead of us and dropped the anchor. The timing was perfect, too: the sun was going down and we were greeted with a wonderful sunset as we settled for the night. I was very proud of us.

Our anchorage site was as quiet as it could be—no wind, no waves. To our port side, there was an ugly fishing boat, and to our starboard there was a gorgeous two-mast, pale-green ship. Needless to say, we preferred to rest our gaze on the starboard side.

Salem Harbor

A morning in Salem Harbor

Waking up in Salem Harbor was magical. I admit that I had considered—just for a few minutes on the previous Friday—bailing out of the trip altogether out of fear that the waves that had been forecasted for Massachusetts Bay would make me seasick. That would have been a huge mistake—on that Sunday morning there was absolutely nothing I would rather be doing than enjoying the amazing sunrise with my friends and drinking my (french pressed) morning coffee surrounded by the ocean.


The morning had another surprise in store for us—seals! Lots of them! They were swimming around the moored boats, occasionally swimming just at the surface and making a big splash. Sometimes we would see their small black heads sticking out of the water. What a show! We watched them for a while, and then a guy came over on his pale green dinghy—he just wanted to chat. His name was Frank and he owned the two-mast boat that I had been admiring the night before. He gave us lots of great tips and where to go ashore. When he left I turned around and saw a feast was taking place in the cockpit table behind me—bagels, cream cheese, smoked salmon, tomatoes, eggs—you name it! Koby had everything (except capers—but I forgave him! :D ).

Frank & a bunch of fish

Frank's boat

Andrew was able to snap a photo of a seal having her breakfast

The boat needed a pump-out so around 9AM I called for the pump-out boat on channel 9. He told us that he would be with us in 45 minutes give or take. We had been very spoiled by the pump-out boat back in Vineyard Haven which had shown up only a few minutes after we called them. In the back of my head something told me that we should probably plan to head back to Boston early…Preferably right after pump-out. But it was so nice in Salem… and I really wanted to go to town (I had never been there before)... And we had come all this way to Salem… Also, I was very aware that this would probably be our last cruise for the year and wanted to make the best of it. So I said nothing.

The crew started preparing the dinghy to go to town while we waited for the pump-out boat. At around 10.15AM there was still no pump-out boat in sight so I called again. We learned through the radio that the guy had some issue with his pump so he would not be able to pump us out for a while. I rationalized that there would be no harm going to town while we waited for the pumpout boat to get fixed. In retrospect, we should have made plans at that point to get to Boston early and get pumped-out there. Well, hindsight is 20/20 and we ended up going to town anyway and using up precious sail hours there. Furthermore, thinking we were doing the right thing, Sergey and I called the pumpout boat and told him to get us off his waiting list since we were not going to be on the boat for the next few hours.

Koby found a dinghy dock at Pickering Wharf using his phone and guided us there (Andrew would have probably argued that the cruising guide would have been the right way to learn that but Koby’s solution did get us there)—it took about 20 minutes just to get to the wharf and dock our dinghy. On the way there, I kept remembering how we had once broken our motor in Hadley Harbor and had to row all the way back to our boat. If we broke our motor now, we would have to row at least twice the distance that we had to row back in Hadley Harbor. As we went around the tiny Derby Wharf Light, a couple sitting on the wharf smiled at us, possibly entertained by the bright orange life jackets that we were all wearing.

Bacalhau-à-braz

At this point I was totally in “island” mode (even though Salem is not an island, but you get what I mean). Sergey and I made the decision to return to the dinghy by 1PM, which sounded reasonable. I think neither of us really appreciated the fact that we were 20 nautical miles away from Boston and that it would take us a good 6 to 7 hours to cover that distance.

We walked along Derby Wharf to go checkout the lighthouse, took lots of pictures, and saw the Friendship of Salem on the way. We were just relaxed and having fun. As we were walking back from the lighthouse, I proposed we had lunch in Salem before heading back to the Eliza. There were no enthusiastic “yeses” but no disgruntled “nos” either so we found a place that had outdoor seating.

That masts that belonged to the Friendship of Salem were lying on the grass and their cleets were huge.

To my surprise, the place we had chosen was a Portuguese restaurant. The main menu was filled with Portuguese dishes! I hadn’t had Portuguese food since my lightning visit to Lisbon in March just before the pandemic closed down borders all over the world. I was thrilled that I got to introduce the crew to a little bit of the Portuguese culture. There’s still a smudge of nationalistic pride in me, I admit. Codfish was never my favorite food growing up in Lisbon, but whenever I find a Portuguese restaurant in the US, I am always compelled to order codfish… perhaps because salted cod is such an odd thing to order at a restaurant.


All of this delight and excitement also meant that I had totally lost track of my priorities at this point. As the appointed navigator, I should have known that we would be very, very late getting back to Boston. Getting back safely to familiar waters before the sunset should have taken precedence over a Salem visit, but it would have been a tough decision that I had not been willing to take.

On our way back to the Eliza we saw what appeared to be a floating, moving, tiki house. Turned out it was a bar. It was around 1.30PM when we arrived at the Eliza, and we still needed to pump out our boat. I called the pumpout boat again but got no response. They must’ve been backed up (no pun intended!). We could not wait much longer. We tried calling the Marblehead harbormaster to see if they could pump us out on the way but got no response either. This was when I realized our predicament: we would not be able to pump-out; we had to return to Boston ASAP to avoid sailing in relatively unfamiliar waters in the dark.

Night Sailing

We left Salem Harbor via Marblehead Channel—Salem Sound was a popular place that Sunday, and there were lots of boats sharing the channel with us. We did our best to tack our way out of Salem Sound, but our progress was slow—we needed to travel southeast against the wind, which meant a lot of tacking before we cleared the Sound. Sergey had considered reefing the mainsail but gave up on that plan given our experience the previous day at Nahant. As a result, the crew had to contend with some heeling (well, maybe a lot of heeling ... I was too focused on the chart and sailing as close to the wind as possible to notice that the crew was uncomfortable… )

The helmsman and the navigator

It took us what felt like forever to get to the red buoy number 4—the part of our course that was supposed to be the “short” one. But it was fun, I admit, to be on a tack facing the open ocean and then back to seeing a familiar (i.e. charted) landscape, zigzagging between the adventure and the familiarity. The only non-fun part was having to dodge lobster traps, there were dozens of them!! It reminded me of that scene in The Empire Strikes Back where Han and Chewy fly into an asteroid field (“never tell me the odds” ;-) ).

It must’ve been around 5PM when we cleared the red number 4 and anxiety settled in–Sergey and I looked at each other, and we both knew our predicament: we had 2 hours before sunset and we were not going to make it to Boston before dark. In a moment of blasphemy and weakness we considered turning on the engine for the passage to North Channel. There was a problem with that though (other than the obvious problem of motoring when we had a perfectly good set of sails)—Andrew had promised the sailing club that he would return the boat with a full tank of diesel. Even if we motored we would not be back in time to refuel (and the tank would not be full). But if we didn’t motor we would be potentially putting the crew in a perilous situation: we would have to sail against the wind, at night in unknown waters and thus unable to precisely track our position or detect rogue waves and treacherous lobster traps with enough time to react. It took one look at Andrew to know that there was only one option in that situation: we were sailing all the way.

Getting ready for some night sailing

The sun disappeared behind the cloud as we cleared Nahant. There was still a long way to go, and soon enough the water would turn pitch dark and the green islands would become dark shadows against the landscape. Our next tack had us facing the Graves Lighthouse, which was reassuring … for a little bit. Then we saw our first lit buoy: a dot and a dash (representing an “A” in Morse code) from the red white buoy that marked the entrance to North Channel. Night sailing had begun.

We still had a long way to sail to get to Boston when the sun disappeared

At this point we could see Boston’s many lights in the distance—some blinking, some not. The new mission was to try to find the “right” blinking lights and avoid the unlit buoys (we would not be able to see them) while at the same time avoiding the lobster traps sneaking up on us. But we had a plan! Since we knew—based on our previous tacks—that we could travel closed-hauled at both 120 and 210 degrees, Sergey and I looked at the chart and figured that we could just tack into the North Channel (~210 degrees) and that heading would take us back home. Turns out we were wrong about the 210 heading (either that or the wind had shifted)—we ended up having to tack between the North and South Channels multiple times. Also, we had failed to account for the huge and very well lit dredging barge that was anchored in the middle of North Channel!

Andrew was at the helm at this point, and he decided to tack before we were too close to the barge. It’s really, really hard to tell how far you are from an object—even a well lit one—when everything around you is dark. The problem with this tack was that we were moving quickly across both North and South Channels and would soon pass beyond South Channel, which had its own dangers in store: Sergey and I estimated that we were heading straight to Ram Head, which is appropriately marked with a green buoy but one that was unlit and thus completely invisible to us—we would not be able to see it until it was too late! So we asked Andrew to tack back toward the North Channel. It was then, I think, when I lost my bearings. Examining the chart felt so safe, as if it was clear where we were supposed to go. But then looking around me, all I could see were blinking lights—from Boston, some from buoys. I was not able to tell if a blinking light was near or far. Was that buoy flashing every 4 seconds or 6 seconds? And how the heck do you count 2.5 seconds?

I had never been so relieved for clearing Deer Island Light before. This meant that we were finally travelling in familiar waters. The familiar President Roads channel was finally within our reach. I relaxed for a few minutes as we made our way to the inner harbor. And then Andrew asked—so are there any obstructions in Inner Boston Harbor? Oops… I was not prepared for that question. I never noticed before! He reminded me of the airport landing strip that stretches out into the Inner Harbor. But where was that on the chart? I looked and looked but it was not there! Koby pointed it out before we found it on the chart. Stressful indeed!

We asked Andrew—who was still at the helm—to steer towards Zakim Bridge and bring us back home. We passed Rowes Wharf, dropped the sails, and that was the end: no more charts, no more planning. Or so I thought. Turned out that the Boston Sailing Center boat house was really hard to identify in the dark. When we finally saw it, Andrew asked me and Sergey to figure out how to approach it and how to dock. We barely had time to discuss it, and Andrew was already reversing into the dock. I grabbed the stern line, jumped on the dock, and totally botched the landing by running forward instead of back. No harm done though—Andrew yelled “tie it behind the stern”, and I did. We finished docking, and we were home safe.

This whole experience—of learning by doing and making mistakes—made me realize how much I used to depend on Andrew to make decisions and to plan our sailing trips. And there are a LOT of decisions: where to sail given the weather conditions? anchor or moor? Where to pump-out? Where to refuel? Will we be able to get back before the nightfall? I admit that most of the time I just want to “wing it”, but that’s not the right approach. It’s not like going on a road trip where you can count on some gas pump to be open at odd hours or some motel to have a room for you in the middle of the highway. There are a lot more constraints in sailing, and you have to work within those constraints.

The feeling I remember the most though was the quiet confidence of knowing where I was and where I was headed: when I was at the helm heading toward North Channel, and I had a firm grasp of the chart and a firm grasp of how my heading and speed translated into a specific course on that chart—THAT felt awesome. If Andrew were a GPS-dependent type of person, I don’t think I would ever have been able to feel that.