The End of Long Island!

Sag Harbor, Long Island, NY – Tuesday, 6/22

Greenport to Sag Harbor

Our day started with Denise going for a run in Greenport.  Leaving the marina she headed down the streets she had walked the previous day, but this time she continued further west to the main highway (NY25) and ran briefly down it past the Lin Beach House and on to Kontokosta Winery, where we visited in 2017 when Claire was aboard.

Afterwards she ran back through town and up and down streets along the waterfront. Here she discovered new condos that had since been built, where once there stood a few older homes, as well as some other interesting sites:

Although we didn’t have far to go (less than 10 miles to an anchorage in Sag Harbor) we wanted to arrive early so we could see some of the village, and also before the forecasted thunderstorms arrived.  So, just after 8:30 we left Mitchell Park Marina and headed out of the harbor, passing the ferry terminal and Shelter Island on our port side. 

We entered the Shelter Island Sound and to our right we passed the town of Southold and the Great Hog Neck.  Soon we made our way through Noyack Bay, around the North Haven Peninsula and into Shag Harbor with its beautiful boats and mega yachts in port; the Ft. Lauderdale of New York.  This is the Hamptons, and the playground of the uber-rich.

We anchored Island Office in the Sag Harbor Cove, where there were only three other boats; one of which left shortly after we arrived.  We then launched the dinghy and took into the Village of Sag harbor.  First we walked around docks to look at all the yachts, then we walked around the downtown and found a shop to buy the requisite magnet (have you see our magnet board at home?).  We walked up and down the main streets of the Village, seeing unique shops, restaurants and coffee houses. There is no Kilwin’s or Ben & Jerry’s here.

Yachts in Sag Harbor – see the car on top the yacht on the left

Soon it was lunch time and we found a small lunch spot recommended by “Debbie” in the shop where we bought the magnet. She had recommended one of their sandwiches on focaccia bread, which we did order.  As this is mostly a pizza joint for pickup and delivery, there was no place to sit down, but there were chairs in front of the ice cream place next door. So we sat outside enjoying a delicious lunch that was so filling we each took ½ of the sandwich home for another meal. 

While eating, we enjoyed watching a police officer coordinating the pedestrians in the cross walk, with the continuous stream of cars coming through the traffic circle.  We can only imagine how crazy this place must be in the middle of the summer with cars and crowds.

Directing traffic for Pedestrians
Traffic circle

We could see the storms were coming in and wanted to make it back to the boat before they hit. We headed back to the town dinghy dock and got into “Cubicle” (nickname for our dinghy) and motored our way back to the boat.

Once we got back to the anchorage we saw another Back Cove (“Family Ties”) was now also there, but the first power boat had left.  We barely made it back in the boat before the rains came.  It poured and there was lots of thunder, but we were well protected in this beautiful cove.

During the rest of the afternoon we did office work, emails and talked with family, all-the-while marveling at the beautiful homes and boats that were within site.  The best part was our accommodations were free! 

House behind at anchorage

Mark also noticed an issue with our shower sump pump; it wasn’t working and the shower was now draining to the bilge.  He spent some time working on a temporary fix, and ordered (via Amazon) a replacement motor to be sent to a future destination (Point Independence Yacht Club) after the July 4th weekend.

Mark working on sump pump

Not wanting to cook and still relishing our tasty lunch, we decided to eat the leftover half sandwiches for dinner.  They were just as good as they were at lunch, and we were happy to relive this party in our mouths.

We found Sag Harbor to be a warm and friendly community. While there is some snob appeal in some of its visitors, all the locals we met were incredibly nice and we were very glad we came to see this beautiful place.

Montauk, Long Island, NY – Wednesday, 6/23

Sag Harbor to Montauk

It was the perfect morning to just sit around and enjoy the beauty of the area. The sky was clear and the air was crisp, but not cold.  We hung out for a while taking it all in, then at 9:30 we left to head to “the end” of Long Island, Montauk.

We exited our anchorage at Sag Harbor Cove, went under the Ferry Road Bridge, passed the mega yachts and sailboats in the marina and moorings, and said good bye to Sag Harbor.

We entered Sag Harbor Bay, passing Shelter Island to our port, and eventually Cedar Point and its lighthouse to our starboard.  Here we re-entered Gardiners Bay only this time on the eastern side, almost completing a full circle around Shelter Island in the last few days. We hugged the eastern coast passing a few large sailboats, one at anchor and the other underway.  They were similar vessels and we wondered if the one was waiting on the other for a meet-up.

The channel turned to the east and we rounded Gardiners Island before heading back north-northeast. Around 10:30 we officially entered Block Island (BI) Sound and cruised along the coast of the north fork of Long Island until we came to the breakwater into Montauk Lake. This was originally a freshwater lake, but in 1927 a developer blasted a gap in the shoreline to provide access to Bl Sound and the Atlantic Ocean.  Today, it is a salt water harbor and home to one of the largest fishing fleets on the east coast.  The harbor and lake are actually a few miles north of the Village of Montauk, located on the Atlantic Ocean side of Long Island.

We approached the breakwater as a USCG boat was maneuvering in and out; we think it was on a training exercise or testing out something. As soon as we entered the breakwater, it returned in behind us. The USCG Station Montauk was immediately in front of us on Star Island as we entered the channel.

Topside Bar & Inlet Café

We took to the eastern side of Star Island and Mark found an anchoring spot that was between the mooring field and the shallows of the lake.  We settled the boat at anchor and then Mark called a few places to see where we could land our dinghy. There is no town dock as they don’t really cater to the cruiser (at anchor or moorings). They prefer those who come in to stay at marinas, yacht clubs or resorts with docks, or private moorings. Therefore, there is also not a launch service.  Finally, he was able to secure a spot for a dinghy at one of the marinas that would let us tie up for a few hours for free.  We just wanted to grab some lunch and walk around the small harbor area a bit.  We launched the dinghy, got in and untied from the boat.  As we pulled away from boat, the engine stalled.  We got it restarted, but when we tried to put it into gear it stalled again.  After several attempts and now drifting with the current, we were forced to immediately break out the oars and row back to boat.  Mark worked on it a bit and thought he had it fixed, even taking it on a test drive. So Denise got back into the dinghy and we started out again, but it again failed. Fortunately, this time we were still tied on to boat.

Now we had a dilemma; to come this far and not see Montauk would be a huge disappointment.  We decided to eat lunch on the boat and consider our options.  After several considerations, we decided to bite the bullet and pay for a marina.  We called Snug Harbor Inn & Marina (a place recommended to us by a cruiser on a boat in Greenport).  They could take us for a one-night only stay, so we booked the slip.  And we are so glad we did.

We pulled up the anchor and moved the boat back through the harbor to the other side of Star Island and went down the channel as far as we could until we came to the Inn and Marina where we docked the boat on a side tie.

We checked in with office and got lots of suggestions for places to eat, things to see and transportation options.  

Snug Harbor Marina

We decided to walk the (less than) mile to the village area around the harbor. Along the way we saw several restaurants and all the sport fishing and whale watching charter businesses, as well as the working docks for Gosman’s, a big fish processor.

Next door were the businesses that overlooked the inlet, including a few touristy shops, a restaurant, and the Topside Bar, where we went for a drink.  The Snug Harbor Hotel staff had suggested the place for its view, and today it was a spectacular day and worth the walk.  Here we met Julie, our waitress who was originally from France, but now lives on a houseboat in our marina.  She was very informative about the area, and even told us about the boat next to her in the marina (more on that later).

Working dock at Gosman’s
Gosman’s Dock – shops and restaurant
At Topside Bar

After a few pictures, a magnet purchase and a walk around the fishing docks, we left trying to figure out how we could get to “town”.  It was too far to walk and there were no bikes to rent.  We had also been considering going out to the Montauk Lighthouse, but it was closed until July 3rd, and the museum was only open until 4 pm, so we ruled it out as a place to spend our limited amount of time.  As we were contemplating walking back to the boat, then getting an Uber from there to go into the Village of Montauk, we noticed a city bus at idle.  We talked with the driver and found out that the bus runs between the harbor, the Village and East Hampton on a circular route.  Our timing was perfect and “Sal” the driver encouraged us to hop on; it would only be 10 minutes for us to get to “town”.  But the best part was he gave us the senior discount and it cost us a whopping $1.50 in total for the ride.

Along the way, Sal filled us in on a lot of history around Montauk and about the people.  He really liked to talk and Mark being a great listener got an earful.  But it was fun and we learned a lot.

Mark talking to Sal

Once in the Village, we first walked a few blocks to the beach.  We were fortunate to encounter a Marine Patrol Officer on the boardwalk who took our picture overlooking the Atlantic Ocean.  We went back into the main street of town and did some souvenir shopping (Mark a t-shirt, Denise a throw blanket for the boat), and took a few pictures.

At Montauk Beach

We were ready to head back to the boat and have a more affordable dinner in the harbor, and nearer our boat.  We walked to the bus stop, arriving about 15 minutes before the scheduled departure.  After 40 minutes the bus was still not there, despite one of the locals telling us that it is never more than 20 minutes late. So we called for an Uber who was there in less than 2 minutes and in 10 more minutes we were back at the boat. It was the best $20 we spent as Denise’s foot was hurting from all the walking, she was cold, and she wanted to change into some warmer clothes before dinner.

We then went to the restaurant at the marina next door as suggested by the Snug Harbor staff.  We had a delicious meal of the freshest seafood (Denise got sushi and Mark got Fish n Chips) and we both loved our meal. The food was good, reasonably priced and glad we came back to the harbor area for dinner.

Now to the story about the boat next to (waitress) Julie’s boat: There is a book called “A Speck in the Sea” (that we have both read) that is based on a real story about a Montauk fisherman (John Aldridge).  He fell off the back of his fishing boat in the middle of the night, 40 miles offshore when his childhood friend and first mate (Anthony Sosinski) was asleep. Miraculously he was rescued and lived to tell the tale. Apparently they have been working on getting this made into a movie.  The boat next to Julie’s is Anthony Sosinski’s current home.  You can read more about this story here.

Anthony Sosinski’s boat

And now about Snug Harbor Inn and Marina: this is a local’s marina, but the inn is an old-school motel that is a throwback to the 1960’s.  Family-owned and operated, the place is very customer service focused, very clean, and well-maintained.  It was a great spot for us and we were so glad we salvaged our stay here so we could experience life at “the end” of Long Island.

And with the close of the day, we spent our last night in New York.


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