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Log 121: A long, long, Long Island Sound

Crew Log for May 20th – 23th, 2023


Trip Summary:

• Port Washington to Cuttyhunk Island

• Trip Distance of 183.5 NM, Total Distance To-Date of 4,924.4 NM


As much as we keep reminding ourselves that the trip down to the Bahamas and the trip back are an important part of the adventure, the reality was, we were anxious to get home. Not only had we been away for 9 months at this point, with few exceptions, our return journey was starting to feel very much like a delivery run. Saying that however, we do have to remind ourselves that we had wonderful stops at Jekyll Island in Georgia, Elizabeth City in North Carolina, Annapolis (Bay Ridge) in Maryland and of course Staten Island and New York City. So, this hasn’t been “just” a delivery run.


We decided our return trip up Long Island Sound would be a quick one. “Quick”, relative to the time it took us to cover a similar distance heading south last fall.


Our first leg was from Port Washington to Port Jefferson, a distance of about 40 nautical miles. It was overcast and rainy. The wind in the morning was out of the east, which meant we’d be beating into it. However, the forecast was for it to shift around more to the south, which should make things more comfortable. We hoped!


On our trip up the East River the previous day, we had been hearing Coast Guard reports of bodies in the water. I checked the news and saw a report that the bodies of 2 young boys, aged, 11 and 13, reported missing from Harlem, were found in river. Somehow, being right there, made it feel all the more shocking.


Given the rough conditions on the Sound, we decided to sail on just the jib. We have had many conversations on this trip about what characteristics would make up the perfect boat. It’s a long list, but close to the top is a furling main. Not only would that eliminate the necessity to go up on deck to reef, but it would also allow a single crew member to adjust both the main and jib, avoiding the need to disturb the second crew member, while we’re on passage.


Long Island Sound is a huge body of water, running east-west. It is bordered by Connecticut to the north and Long Island, New York to the south. It is a popular boating area, and sailboat races and sports fishing are common. However, when the east wind is blowing, conditions on the Sound can get rough and cold.



As we beat our way along under sail, I noticed a large, commercial fishing charter boat coming up behind us. They had their AIS turned off which is the first clue that a cowboy is behind the wheel. I radioed the boat, indicated we were under sail and asked if they could they divert their course to avoid us. Silence. I radioed again. Silence. We quickly started the engine and made an erratic turn, just as the charter boat went directly across our bow, less than a boat length away. The cynic in me says it was an intentional act designed to entertain the 20 or so “fraternity bros” on deck.


Later in the day the fog rolled in and it started to rain harder. Visibility was starting to be a challenge so we turned on the radar. However, as the wind shifted to the south and the tide changed, we found ourselves doing over 7 knots on a reefed jib! We quickly forgot about the rain and fog.


The entrance to Pork Jefferson is through a narrow opening, with rock breakwalls on either side. It is well marked and fairly straight forward. However, just as we entered the channel, a ferry was leaving Port Jefferson. Fortunately we were well inside the breakwall by the time it reached us, and had adequate room to stay out of its way. We arrived just before 1700 hours. It had been a long challenging trip in the rain. We grabbed a mooring ball, had a bite to eat and went to bed.


The next morning, we woke to cloudy skies, cool temperatures, with 8-10 knot W-NW winds, with gusts to 15. We were headed up the Sound and across to Old Saybrook, where we waited out Hurricane Ian, last fall. We hoisted the main, rolled out the jib and enjoyed a nice beam reach sail until the wind went further to the west and eventually died completely.


We had gotten our first update from sv Beyond, who were with us at Staten Island. They were just off of Liverpool, Nova Scotia, in 40 knot gusts and had just taken a wave over the back, that filled the cockpit. They were doing OK, but in BettyAnn’s words, “it was not your average Sunday family sail”. It was good to hear from them and we hoped they’d be alright. Judy and I both agreed that taking the slower course was the right decision for us, given we are on a much smaller and much lighter boat than Beyond.


Things were far less dramatic on Elizabeth M. When the wind dropped, I actually went below and made bread. While I waited for it to rise, I posted a blog from our ICW Series and reflected on the marvels of technology. Baking and blogging in the middle of Long Island Sound.


We arrived on an ebb tide, which meant we were battling a pretty stiff current at the entrance to the Connecticut River. Just to make things more interesting, there were a couple of jet skiers “playing” in the channel and, what seems to be a familiar refrain, cowboys in power boats. “Reel Dazed” seemed to be appropriately named given the way he operated his boat, although “Real Stunned” seems more accurate.




Old Saybrook is a harbor of refuge. Mooring ball owners are asked to attach a yellow marker on the balls if they are away for more than a couple of days. Visiting boats can moor for free, provided there is a ball available. When we were here in the fall, the place was almost completely full, however, there were only a handful of boats in the water this time. There were dozens of swans though.



The North Cove Yacht Club was having an opening ceremony, signaling the start of their new year. As we grabbed a mooring they started to play the Star Spangled Banner and, just as Judy was finishing tying us up, they let off a single canon shot. Luckily she didn’t fall off the bow, ducking for cover.



Supper, sleep and back at it again in the morning.


We left Old Saybrook right around 0700 hours in order to catch the outgoing tide. Our plan was to sail the 40 plus nautical miles to Block Island. We were sailing with a full main and jib on a close haul. The sea was relatively flat and winds were from the north. Despite the forecast for sunshine, we noticed a distinct hazy, which we later found out was smoke from forest fires.


One of the most challenging stretches of water on Long Island Sound, is where the water wraps around the Long Island Coast. “The Race” is a 3 mile wide deep water channel of turbulent water caused by the tidal exchange the waters of Long Island Sound and Block Island Sound. The bottom is said to be shaped like a rollercoaster. Given the volume of water that flows through here, the tidal currents can reach 4 – 5 knots, creating white water waves and chop.


As we approached, we received a notice to mariners on the VHF indicating a Canadian warship was leaving the harbour. We looked closely and saw what we think was a Canadian submarine heading out to sea. We didn’t think any of our subs were functional, but there it was.




When we hit the opposing current at the Race, the boat felt like it came to a complete stop. The water was a churning mess, with waves going in every direction. Despite a favorable wind, the currents were just too strong for us to sail. Shortly afterwards, the winds shifted back around to the east, right on our nose, and the final 4 hours were brutal, as we beat into it. We were also freezing!




Block Island is located 9 miles south of mainland Rhode Island and 14 miles east of Long Island. It covers less than 10 square miles, with a large protected lagoon in the center. Starting in mid June, through to the end of September, finding a spot in Block Island is next to impossible. While only 1,400 people live here year round, the island is a popular summertime destination for bikers, hikers, sailors, fishermen and beach lovers. And while it is covered in summer homes, 40 percent of the island is set aside for conservation given it is a strategic location for migratory birds, travelling along the Atlantic flyway.


We had not been off the boat since we left Staten Island, so we were looking forward to exploring Block Island. Unfortunately, it was late, it was cold, and it was off season, which also meant there wasn’t much to see or do in Block Island, other than fill our diesel cans. It was a bleak looking place, although I’m sure we saw it at its worst.


It had been a tough few days coming down Long Island Sound, but we still had Block Island Sound and the infamous Buzzards Bay to deal with before we reached Onset, where we planned to shelter for a few days. We were also tired. We basically sail, eat and go to bed, and other than that few minutes to fill our diesel jugs, we hadn’t been on firm ground going on 5 days. It was emotionally and physically exhausting.


Our log notes for Tuesday start with, “…the wind direction sucks for getting east, but we need to shelter by Wednesday night…”. Our destination was Cuttyhunk Island, 48 nautical miles away. In addition to the east winds, the breeze was cold. Once again, the morning’s sunrise was more like a red ball, due to the forest fire smoke obscuring the sun.



I’ve tried a few times to capture on camera a few times the erratic wave patterns, but a picture or video never seems to show what it really like. It looks like a giant washing machine with the wind, ocean swell and tidal currents pushing the waves in every direction. It was a frustrating day to say the least. The wind was directly on our nose, so we decided to sail off the wind, rather than pound into it. Unfortunately, we had current against us, which meant we were moving slowly. Since we were tacking, we were making very little headway, and we were covering a lot more miles.



When we first visited Cuttyhunk Island last fall, it was after we waited out Hurricane Fiona and experienced a particularly bad day crossing Buzzards Bay. Then, like now, we were emotionally exhausted. Judy’s sister Ruth, our number one fan, advised back then, we go for a walk on the beach, which we did. It was far from a “beach day” then, but somehow, walking on that beach at Cuttyhunk was like some miracle drug that restored our energy.


We arrived at Cuttyhunk right around 1600 hours. We have a routine that we follow after every trip and we occasionally pause and debrief on the day. Today however, we quickly tidied the boat, completed our chores, dropped the dinghy in the water and headed for the beach.


The first thing we noticed was a sea of pink and white wild roses, that immediately reminded us of home. We then saw that the air was full of sea birds darting in and out of a nesting area surrounded by caution tape and signs asking people to stay way. As we wobbled over the rocks towards the beach, the comparison to the beach at Judy’s family “camp” was obvious. As we got closer to the beach, we heard the sound of breaking waves which, given they didn’t result in “rocking the boat”, created an immediate sense of calm. It was all very "zen like" after 183 nautical mile pounding we experienced coming from Port Washington.






We had been on the boat for 5 straight days, which I am sure sounds insignificant to sailors who have crossed oceans. However, for us, as we sat on that beach at Cuttyhunk and took in everything around us, the accomplishment started to sink in. Just like our visit in the fall, that beach energized us. We were feeling pretty good as we made our way back to the boat.


There had been only 1 other boat here when we came in, but a couple more arrived while we were at the beach. We weren’t sure whether the Harbormaster would bother to come out to collect the mooring fees, but he eventually did drop by. We chatted about their road, sewer, and water upgrades, that they started when we were last here. He also mentioned that there had been a boat here the day before from Nova Scotia but couldn’t remember the name. Who needs a newspaper or internet when you can chat with the Harbormaster.


The forecast for tomorrow was for light winds, and finally, out of the south. We also had less than 25 nautical miles to go to reach Onset, about half what we had been averaging over the previous 4 - 5 days. We were expecting nasty weather over the next couple of days but knew that we would be completely sheltered from it in Onset.


We also planned to take a break for a few days, have a shower and eat some pizza. While in Onset, we would hear about how fellow Nova Scotians almost lost their boat off of Block Island a couple of days before. We also transit the Cape Cod Canal and head to Provincetown, where we learn about the town’s long LGBTQ+ history.


But more about that, next time.


Additional photos:













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