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.

Onwards to Marblehead

Crew: Andrew, Koby, Lena

There are days in Boston Harbor when the wind is so weak and feeble that I wish we had a third or forth sail to grab as much of it as we can. Then, there are days like August the 30th, 2020. The forecast had warned me of wind gusts up to 30 knots and seas with 2-3 ft waves so I had a vague idea that this was going to be a day of intense sailing which would require skill and caution. I had worked on mentally preparing myself for what was to come, on remembering that the only way to grow is to be comfortable with being uncomfortable. In strong winds a sailboat can easily become overpowered—for that reason, the mainsail in most boats is rigged to allow one or two reefs, i.e. to reduce the amount of sail surface that is exposed to the wind by means of a set of lines that pull the sail down and secure it over the boom and back toward the stern.

I took some pictures of the water around the sailing club as I waited for the rest of the crew. The water appeared calm; “Maybe it will not be as bad as I imagined”, I remember thinking. We left the marina in the Aeolus—a blue Sabre 30 owned by the Boston Sailing Center. Our exit from the slip was smooth and with the west winds to our stern we were soon on our way to the outer harbor. We didn’t notice until we were pretty far from the marina and ready to raise the mainsail that our boat was rigged for the first reef but not the second. When Andrew pointed it out, I didn’t immediately fully appreciate what that would mean for our ability to steer and control the boat.

The water around the sailing club appeared calm and serene

As we approached Castle Island, Andrew asked me to pick a destination. We could go southeast or northeast. After some discussion, we decided that we would try going northeast—we might even be able to reach Marblehead, something that this crew had attempted before but had run out of wind and ended up anchoring in Nahant instead. Going north seemed like a good idea, not only because we had been mostly sailing south this year but also because Andrew expected (or rather hoped) that the wind would veer northward and become northwest, which meant we would be returning home on a beam reach.

Andrew’s note: I was glad that we decided on Marblehead. We rarely go there for a day sail. It's 18 nautical miles from Boston to Marblehead. Since I refuse to go under motor (unless cornered), it’s only possible to comfortably do the round trip in a day if the wind is just right. In fact, I think it was just the third time in my life I'd done it. The first time was years ago, when I was learning to sail and took a coastal navigation class which included a day trip to Marblehead. That was also the first sail in my life outside of a harbor. Fortunately, we were practicing the traditional paper-chart-and-compass navigation back then, and I was just thrilled by sailing a compass course and then, after an hour or two, seeing the buoy we were heading to magically appear at the horizon. And then, of course, Marblehead itself is a cute town to visit, and Salem Sound (the body of water from which one enters Marblehead Harbor) is an interesting and challenging place to sail. Turned out it had some new surprises for us, too.

The waters began to appear choppy as we approached Castle Island

Turning toward the North Channel after Deer Island was when I first felt the full might of the wind—and the impact of that missing second reef. The gusts and the waves made the Aeolus very hard to control and even though I had been trying to hold on to the wheel and keep her steady and on course, my shoulders started to hurt from the stress and the tension and I had to ask Andrew to take the helm. We were travelling at a respectable 7 knots and were zooming past buoys but she was definitely putting up a fight, occasionally heeling intensely due to a stronger gust or two.

Moving past Nahant

At 11AM—a mere 2 hours since we had left the marina—we were by Nahant. There was therefore no reason not to aim for Marblehead. The conditions remained the same as Andrew diligently kept her on course toward the red buoy number 4 which was 6 nautical miles (or about 1 hour) away from the red and white buoy marking the beginning of the North Channel. Koby and I adjusted the sails occasionally but mostly remained silent and enjoyed the wind in our faces.


On passing red number 4 the gusts intensified and Andrew felt it was time to further reef the jib, i.e. to furl it even more to reduce its power. Still in charge of navigation, I gave Andrew the instructions to arrive at our next target—a red and green buoy marking the entrance to Salem Sound. The required heading and distance were clearly annotated in the chart (I would have had to use a ruler otherwise), but I still felt proud of playing the navigator role—this was the first time that I was doing it alone.

Our plan was to leave the buoy to our port side and then tack to enter Marblehead Harbor. Instead, as we approached it, I saw a partially submerged lobster trap floater cross our bow. When I heard the captain utter the words “we have a problem”, I knew we were “trapped”—in all meanings of the word. The line connecting the floater to the trap had got caught either on our propeller or keel and even though we had plenty of wind, the boat was stopped, and Andrew could not steer. He suggested that we jibed her in place instead. After making sure that there were no heads on the way, Andrew used the jib to turn the boat away from the wind and the boom swinged violently toward our starboard side as the wind caught the sails on the other side. Something was happening—we were moving—but it was not clear to me whether we were moving forward or rotating around the trap. After a few agonizing seconds wondering if we had regained control of our ship, I saw the guilty floater a few feet behind us—we were free!


Marblehead Harbor was finally within reach, so we dropped the main and turned on the engine; it was time for some relaxation! Marblehead Harbor was a sea of boats with a little bit of water in between. The deeper into the harbor we went, the less windy it became. We followed the tiny channel between the moorings and the shore which led us to the town dock, where we were able to easily dock thanks to the practice we had done the week before.

There were lots of boats in Marblehead Harbor and a few sailors having fun

Then came the gourmet lunch—which always happens when Koby joins the adventure and gives us the pleasure not only of his company but also of his cooking. From the galley and by Koby’s hand, food kept coming up to the cockpit—bread, multiple types of sandwich fillings, cole slaw, crab salad and of course wine! We ended up having a very pleasant, very filling lunch under the sun with almost no waves and no wind.

Food kept coming up to the cockpit

Andrew and I went for a walk after lunch (Koby stayed with the boat as the harbormaster did not allow unattended boats in the town dock). We came across a lovely park with great views of the harbor and a lot of “in loving memory” benches, water fountains, statues and other memorials. Looking down into the harbor helped us fully appreciate how busy this harbor is: there are about 2000 moorings crammed in the 1 mile-long, 700-yard-wide horseshoe-shaped harbor! There’s also an interesting tidbit of maritime history that I didn’t learn about until later: Marblehead Harbor was home to the first armed vessel of the United States Navy (originally called Continental Navy). The town of Marblehead—originally called Massebequash—used to be home to the Naumkeag people, who were unfortunately decimated by smallpox (or so it is believed) in the 1600s, and it was later colonized by European settlers, who renamed it "Marblehead" when they mistook its granite ledges for marble.

The Aeolus quietly awaiting her crew (lower left) in the town dock at Marblehead Harbor

A little castle

Back into the fray

With the wind pushing us away from the dock, our undocking maneuver was easy, and soon enough we were back in the small channel that would lead us back to Salem Sound. We had partially unfurled the jib before we left the channel, and I was at the helm. As soon as we left the protection of Marblehead Harbor, I could feel the strong wind on the jib. As I turned her into the wind with the intent of allowing Koby and Andrew to raise the mainsail, I felt extremely strong resistance from the jib, which was turning our bow away from the wind—with full throttle on the engine I still could not keep her facing the wind, so that Andrew could work on setting up a second reef on the mainsail. In retrospect, having the jib unfurled before raising the mainsail in these wild wind conditions was probably a mistake: live and learn!

Eventually, I freaked out about the lack of control and asked Andrew to take the wheel while Koby and I attempted to push the mainsail down and backwards with a makeshift second “reef” line that we had tied to the main and wrapped around the boom. Our reef job was ugly—we had nothing but sail ties to try to keep the lower part of sail from filling with air, but our combined strength could not compete with the power of the wind and there was only so much we could do about tying the main to the boom. Even with a handicapped main and a reefed jib we were moving at about 6 knots. Relieved that Andrew was at the wheel and that we had reefed the sails as much as we could, I sat down and settled—I had had enough excitement for the day… or so I thought!

The return to the North Channel was uneventful—even though I was tempted to fix the ugly second reef job, it would be too dangerous to do so: Andrew would need to turn her into the wind to release some of the pressure on the sail, but that would have made the sail luff so violently that it would have been a danger to the crew. I was glad I decided to not do anything about it. Until, that is, we turned into Presidents Roads to take her back home.

With the wind coming directly from the northwest, which was our heading, the handicapped/reefed sails meant that we had to sail her at a large angle relative to the wind direction. We were heeling a lot but moving slowly. To make matters worse, the wind was pushing us toward Spectacle Island. We tacked to avoid a collision with the island but did not have enough speed to cross the “no-sail” zone due to our handicapped main and our jib trying to turn us away from the wind. I had experienced this many times while sailing on the Charles River (in fact, the only time I capsized in the Charles was caused by a jibe tied directly to my frustration at the inability to tack due to lack of speed), but it had not occurred to me until that very moment that the heavier the boat, the more speed it needs to tack successfully. And we did not have enough speed for our heavy boat.

Andrew quickly turned on the engine and we were soon getting out of that perilous situation. And then, he taught me and Koby a new technique that I had never learned before: backwinding the jib while tacking. So here’s how it worked: every time we tacked, we would allow the jib to catch the wind on the opposite side before letting it flip over entirely to the other side. The intent was to use the jib to help push the bow across the wind (to help us rotate past the “no sail zone”) until we were safely tacked instead of in irons—and it worked! According to Andrew, this is often used as a tactic when racing to minimize the inevitable speed loss caused by crossing the wind.

We tacked a few times within Presidents Roads but left the engine on… just in case. Poor Koby got violently hit by the whipping jib sheet a few times before he learned to stay away. As we approached the inner harbor, the wind slowed down, the sun was low, the full moon showed up and we saw two of the most beautiful ships in Boston Harbor sail into the sunset: the Liberty Clipper and the Adirondack III. It was an idyllic setting after a fun—but intense—day on the water.

Liberty Clipper (left) and the Adirondack III (right) sailing into the sunset

Writing this blog a week later, I appreciate that the most important lesson I learned that day was that sailing in heavy wind is part of learning to become a good sailor. It is fun to do it for the challenge and the pride of having done it, but I always need to remind myself that these conditions need a lot more preparation, focus and attention. I can’t express how grateful I am to Andrew for being willing and able to take me out in these conditions and for patiently holding my hand when I inevitably panic and mess up. Overall, the day was very successful, and in spite of the intense pressure on our sails, the only thing broken was the cockpit table which came off of its support when I was bringing it down after lunch (and that had nothing to do with the wind!).

Sunset sail around Long Island

Crew: Andrew, Koby, Lena, Lena, Sergey

When I used to sail at the CBI in the Charles River, I learned about an interesting weather phenomenon that I had never noticed before: the wind speed tends to decrease around the sunset. This happens because the surface of the earth cools down faster than the air above it when the sun goes down. As a result, the air above the surface continues to move but—because of the temperature difference—it can no longer easily mingle with the colder air at the surface, which becomes still.

On August 20th 2020, we experienced this phenomenon once again. We had had a late start—it must’ve been around 6.20 when we left the dock and ventured into the harbor. Our boat this time was the Emma—a Beneteau 343 owned by the Boston Sailing Center and a twin sister of the Anne, which we had sailed to Martha’s Vineyard and vicinity back in July.


There were a lot of boats in the inner Boston Harbor that day - two races were going on, one on each side of the harbor. We had to zigzag our way around the racing vessels in order to find a good spot to raise our mainsail safely. The wind was good, I took the helm and the adventure started.


With the wind behind us, we quickly made our way toward Castle Island, and we were not the only ones: to our starboard, two boats ahead of us were moving fast—could we beat them, Andrew asked? One of them was only sailing with the main sail, so maybe it was our best bet—the other one was closer to shore but had both sails raised.


As we approached the jib-less boat, we noticed that it was not just another sailboat in the harbor, it was a boat with a political message—they had a flag and a placard promoting a Senate candidate that I had never heard about. They had a bunch of young women at the bow with a few guys at the stern. A very different type of sailing for sure. My attempt to overtake them totally bombed—we sailed neck to neck for a while, with maybe 10-12 feet between us—and then they jibed away and left us. Behind us, the Adirondack III, one of the prettiest boats in the Boston harbor, was quickly making progress. Another boat—more modern and faster than ours—zoomed past us; it had a certain ”Special Sauce” about it.

The Adirondack III

We had decided to go “under” the Long Island Bridge, but as we approached it with Koby at the helm, we heard a fast ferry behind us—we did not want to share the small space between the bridge pillars with them, so we stalled a bit to let them through. Then we saw another ferry coming our way—this time from the opposite direction. We had just enough time to move past the pillars before they reached us. Then we saw a third ferry behind us coming our way!! They honked their horns at us. Bad timing to be under the bridge!


While all this ferry excitement was going on, the sun had begun to disappear behind the Boston skyline - it’s always amazing to me how fast it disappears entirely. Like clockwork, the cooler air at the surface of the earth came to a halt and we were suddenly without wind. This, it turned out, was a great opportunity to enjoy the gourmet dinner that Koby had graciously prepared for the crew - sushi, noodles with peanut sauce, salad and his special blueberry drink that he called “Blue Sky Over Boston”.


As dusk turned into darkness, Boston Harbor was transformed—green islands were replaced with dark shapes, the bright blue water turned dark blue, and all sorts of lights started making themselves visible all around us. I could see Boston Light in the distance, and I suddenly became much more aware of the soothing sounds of the water all around us.

The night was silent and solemn. Nobody was in a rush. The engine remained off as Andrew worked with what little wind he had. As we cleared Long Island and approached Nubble Channel—another place in Boston Harbor which looks very different at night—I felt it on my skin first and then I heard it in the water: the wind was back! We were moving!

Since the buoys that mark Nubble Channel aren't lighted, Sergey walked over to the bow to shine a flashlight on the buoys so that we could see them and safely transit through the channel. After Nubble Channel we entered Presidents Roads—another channel that looks very different at night.

Andrew asked me to navigate, and even though I had looked at the Boston Harbor chart hundreds of times, there were always new details to notice—this time, the important detail to look for were the timings between flashes for every pair of buoys between us and the inner harbor. Unlike the last time when I had sailed in Boston Harbor at night with Andrew, this time I was wide awake and able to appreciate the challenge of finding those camouflaged blinking lights against the backdrop of the Boston nocturnal skyline.


Moving green, red and white lights in the horizon were the only hints that there were other boats navigating in the dark harbor. The wind was blowing, I was happy. Koby saw a shooting star in the sky, and Sergey noticed fireworks over south Boston. As we approached Castle Island, the pleasant sounds of water gushing past our hull were replaced with the sounds from the inner harbor - a boat being loaded at the loading dock, cranes moving, containers being dropped. On the other side of the harbor, the sound of airplane engines was another annoyance disturbing the sea soundscape which we had left behind us.

As we approached the sailing club, the jib whispered “please don’t furl me, I want to be free!”. But that was not to be; we furled her anyway. Someone in the parking lot was blasting smooth sweet music that carried over the waters and helped us relax. Maybe it was the music, maybe it was practice and skill—but we had one of our best dockings in a while.

As I reflect back on that night, it strikes me that—even though there is a sunset every day—I rarely get to see it. These special nighttime sails when we get to see the gorgeous sunset and the stars feel like travelling away to a distant world through a magic portal—a world without stress and without zoom meetings. I can’t believe how lucky I am to be able to do that once in a while.

There is rain at the end of the world

Crew: Andrew, Koby, Lena, Sergey

Sunday the 16th of August was one of those typical Boston summer days that felt a lot more like fall... The weather had been hot for a few days the week before–some might say too hot–before the northeast winds took over and made the temperature dip to 17C. Nevertheless, I woke up excited–it was going to be my first sail day in 2 weeks so a sailing day was well overdue–nothing was going to stop me–not the cold and not the rain!

My time in Ireland had taught me that ‘there is no such thing as bad weather, only bad clothing’, so warm and waterproof layers were definitely a must. When Sergey and I arrived at the dock, Andrew and Koby had already removed the sail cover on the Nelli–a Beneteau 34–and were ready to cast off. Andrew had planned to do some docking practice in Charlestown, so we motored there first. I found it interesting that telling myself that docking was just ‘practice’ made me pay special attention to the details and perform better than I would otherwise. Life is but a sequence of experiments and experiences.

We managed to successfully dock and undock a few times, with different people at the helm so that everyone could learn and build the intuition on approaching the dock at a 45 degree angle and then turning her into the wind. Until, that is, a couple of guys from the dock came to tell us to knock it off. That was the end of our docking practice exercise. We left Charlestown behind and raised the sails - it was time to start sailing.

The wind was blowing from the northeast so when Andrew asked me to decide where to go, I thought that a southern heading might be a good idea. With my finger over the chart, I drew an imaginary line going southeast and Hingham Bay was where my finger stopped - why not go there? The first time that I had sailed there with Ben and Andrew had been a cold day with 4ft waves–and the protection of Hull Bay had given us relief from the waves. Andrew considered that option for a bit and then said–let’s go to World’s End!

Choosing a course for our adventure

With the wind on our side, we made good progress toward and under the (missing) Long Island Bridge, then past Sunken Ledge and toward the West Gut channel that would bring us to Hingham Bay. With every sail, I feel my confidence as a navigator increase, my intuition for mapping the chart to the water and the water to the chart improving. The waters were peaceful–contrary to the 2-4ft waves that the National Weather Service had warned us about–Andrew steered while Sergey walked around the boat, from the bow to the cockpit, from the cockpit to the bow as he often does. Koby, who had brought a fishing rod, tried to troll for fish while I entertained myself by taking pictures around the boat with Andrew’s camera.

Hull and Hingham Bays were becoming two of my favorite places to sail - not only were they fairly well protected bodies of water close to Boston, they also had a lot of interesting things to see and to visit. There was a narrow channel that we could use to travel toward the mooring field on the east side of World’s End. Since our passing through the channel would be against the wind, Andrew decided to drop the sails and motor through. The channel transit was fun - to our port side, private mooring fields and plenty of boats and houses; to our starboard side, raw untamed nature. We moored in a nearly empty mooring field just at the right time - as soon as we started setting up for lunch, rain started to fall.

We ended up having a delicious gourmet lunch in the salon below deck. Lunch included rare treats such as vichyssoise, New England corn pudding, spaghetti squash casserole, small pastries and garden fresh tomato with mozzarella salad–all compliments of cook Koby. Since it was still raining after lunch I decided to lie down in the salon … and promptly fell asleep! Maybe it was because of the happy juice that Koby had made (spiked with rum, of course) or maybe it was the rain. When I woke up I noticed that I had not been the only one asleep–Sergey was right there with me!

Lunch and a nap

The rain had stopped, and even though I was feeling lazy and relaxed (and sleepy), we inflated the dinghy and rowed to shore in order to visit World’s end, which was lovely! We saw a deer grazing, took lots of pictures and walked to ‘the bar’ - a piece of sand that separates World’s End from Planter’s Hill. The walk was pleasant and rain-free, albeit busy–we were not the only visitors: plenty of other families and their dogs had decided to visit World's End on that day. The site had been proposed in 1945 as a location for the United Nations but fortunately for us (and the deer), New York City was chosen instead!

Deer at World's end

The Nelli and an interesting boulder

Since we had not found anything to tie our dinghy to at the beach–and the tide was rising–we did not linger in World’s End for long. We pushed the dinghy back into the water and rowed back to the Nelli. Because we could (the wind was behind us) we departed from the mooring under sail power, which always makes Andrew happy, and returned through the same channel that had brought us there. One key advantage of not using the motor was, of course, the silence, which allowed for the sounds of nature to take over.

We had not yet left Hull Bay when I felt the first few drops of rain. It was starting to rain again. Sergey had proactively put on his bright yellow foul weather gear and Andrew asked him to steer. The cold and persistent Boston rain continued as we went through Hull Gut and turned toward Nubble Channel and then the small boat channel to return to the inner harbor.

Reflecting back on this adventure a week later, it strikes me as odd that I remember the details of West Gut and World’s End so well.. Yet I can’t recall many of the details from the second part of the trip–the cold and uncomfortable return to Boston.

Andrew’s note: I am surprised that Lena doesn’t remember going through Hull Gut, arguably the most challenging place in Boston Harbor: definitely the one with the strongest current, strong enough to overpower a sailboat in light winds. As we were going through, Koby was recalling that, growing up in Hull, they would specifically drive to the tip of Hull to watch the passing boats having trouble in the Gut. We were going against the current, and lost most of the wind, and were making very, very slow forward progress—at times it felt like we were not moving at all. I was already considering the next steps (either turn the engine on, or give up and go back), but then we finally emerged on the other side. With the current weakening every second, and the wind picking up, we started moving again and sailed on, away from this difficult place.

This crew has sailed in Massachusetts many times and faced plenty of uncomfortable and inclement weather. However, we keep coming back.

Sometimes I wonder what draws me to sailing. Warm days and sunbathing on the bow is the image that sailing charter companies sell. And yet, there is so much more than that: sharing experiences, pleasant and unpleasant, solving problems, working as a team and learning to trust each other. That, for me, is the true nature of sailing.