New York to New England

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After leaving the boat in the Brooklyn Marina for three weeks, we headed back for a 16-day end of summer tour to see all the great islands and places we had been reading about for years. For many people, boating in this region is their backyard but for us it was unexplored territory, and that exploration is the magic of cruising.


We flew into Newark because LaGuardia was shut down due to Air Force One landing. Then we realized it was September 10th and we were going to be in the city for the  20th anniversary of September 11th! For some reason we found this a bit nerve-wracking and as we went to bed on the boat, facing Wall Street there were two bright lights shining up in honor of where the twin towers stood. Apparently, we weren’t the only ones concerned about security, on the morning of the 11th we headed up the East River and there were patrol boats every 200 yards surrounding Manhattan. Every branch of the military was on the water that day, so we motored northeast past the UN building and took in all the sights. Entering Long Island Sound was a thrill for us, and we were happy to get to where we had planned to go when we left St. Thomas four months earlier.

Piano Man

Our first stop was Oyster Bay, where we have friends who would show us around and take us to lunch the next day. We dropped anchor across from the wharf in front of an island with some beautiful houses on it. That night for Rose’ time we decided to play Billy Joel to honor the legend he is in this area, and the song “Downeaster Alexa” memorializes it like no other. It was a peaceful night and great anchorage. The next day as our friends were dropping us back to the dock for our dinghy ride back to the boat, Lennie remembered to ask them “hey where on Long Island does Billy Joel live” They pointed to the massive Brick house right behind our boat and said “right there, your anchored in front of it”. Ha, serendipity.

A tale of two cities

Our next stop was Port Jefferson. We had a decent sail downwind with the parasailor and arrived around 5 pm. Port Jeff, as it’s known, has a beautiful, long protected bay and a quaint working town with historic buildings and some not so historic – like a massive power plant right on the harbor. We liked the place because it reminded us of some of the quaint California ports we had visited. Rustic and swashbuckling! From there, we headed to Sag Harbor not knowing what to expect. When we arrived we saw the yachts on display including hundreds of high-end sailboats both catamaran and monohull. This place looked like Saint Barths and if you know Lennie and I you know we like rugged and rustic and high end and fancy in equal measures and this place didn’t disappoint. It’s at the center of the Hamptons and we ended up spending four days with our rental car touring wineries, visiting Montauk out on the bitter end of Long Island, and enjoying plenty of three hour Rose’ infused fabulous lunches. Yes, this place is great and I can’t say enough about it.  Having been tradewinds tropical sailors for so long I just never understood the crowd that goes back and forth from the northeast to the Caribbean like a migration pattern but now we get it. Sag Harbor in summer we will see you again.

We have never sailed to a sailboat show

Our next stop was jumping off from Long Island and the Sound to Block Island (20 miles) and boy did that change things. Block Island is part of Rhode Island, and the vibe was considerably different starting with the houses adorned with shingle siding – that in itself tells you where you are. We sailed all morning and arrived by lunch and made our way into the Great Salt Pond which is correctly named. We spent two days here riding our bikes and crisscrossing the island investigating lighthouses and trying the seafood restaurants and raw bars. A lot of people bypass Block and head for the swanky Nantucket, but we enjoyed this place. After this we left Salt Pond and headed North about 25 miles to Newport and halfway there, we went right through a major regatta and had to navigate past 100 boats head on with their spinnakers flying. It was quite a sight. We arrived in Newport around 3 pm and the timing couldn’t have been better. We sailed past the famous mansions on the cliffs and into the harbor with the beautiful New York Yacht club to starboard and what seemed to be thousands of sailboats of every description. This is the US sailing capitol for sure. Move over Annapolis. As planned, we arrived on the first day of the Newport Boat Show, so we tied Happy Together next to Gurney’s Resort and geared up for a weekend of exploring the boats and gear of the 2021-2022 show season. We saw plenty of friends from the industry and lots of followers of our YouTube channel.  We toured the mansions and did the cliff walk. Newport didn’t disappoint.

All this way

We left Newport after four days and headed to our final two stops of Nantucket and Martha’s Vineyard. Its 65 nautical miles to Nantucket and we made it by motoring in flat calm conditions. We tied to the main wharf marina and started exploring the downtown with its cobblestone streets and intense whaling history. I will say they take the historic cobblestone sidewalk thing too far because you actually have to look down to avoid tripping in areas where the sidewalks are jacked up 6-10 inches. I couldn’t get over thinking about how many people must trip and fall per year in that town. We rode the bikes to beaches across the island each day and ate at some of the best restaurants we have ever been to. It’s a beautiful place and the furthest north of our northeast tour this year. I can’t tell you how many people emailed me and said “you are so close to Maine you have to keep going”, but we are commuter cruisers and don’t live on the boat so this year it wasn’t going to happen – but Maine isn’t going anywhere and we will be back. Our best sailing day of the entire trip was leaving Nantucket in a strong 20-knot north wind and heading 18 miles to Martha’s Vineyard. We flew the code zero and full main and averaged 10 knots, which is flying for us. It was great to be sailing again. This trip is full of land-based activities so the boat is not being used like it is in the Caribbean but we needed this day to remind us how much we love sailing.  We arrived at the Vineyard and spent another 3 days exploring the towns and beaches and lighthouses. Another great stop, and the town of Edgartown is even more picturesque than Nantucket in our opinion. Lennie’s sister and her boyfriend arrived on the ferry and helped us celebrate the last few days of this amazing trip that we have been anticipating for years.  Captain Richard will now pick up Happy Together from Newport where we left her and sail her to Annapolis where Lennie and I will come in for the show and then prep her for our 1000-mile sail back to Nassau Bahamas in early November.


That is what is on our boat jobs list. Happy Together couldn’t be more “dialed in” and it amazes me just how well everything is working from electrical, mechanical and all sailing systems. We are using this boat hard and covering lots of ground – 2,500 nautical miles since we left St. Thomas. There, I said it. Now I better go knock on wood.



14 Responses

  1. Leland Crenshaw

    So good to hear about your new adventure. I am currently bed ridden for a while and love hearing from you. Bless you both .

    • happytogether

      Hi Leland, You have been with us a long time! I hope you recover soon! Randy

      • Chris Sauter

        Curious how would we talked to you?
        Could I get a email?
        I’m sure you get this all the time but my wife and I are interested in doing sailing in a year from now, and you have been an inspiration for us to watch your videos.
        Thank you, Chris Sauter

  2. Dave Klain

    Love the notes and am so sorry we missed you on your pass through the Bay both North and Southbound…and to think I’ll miss you in Annapolis by one day! But like you and Lenny, work has to come first to make the money to support this sailboat habit. Hope to see you either this winter or next summer…

    • happytogether

      Hi Dave, Yes sorry we missed but work comes first…..Randy


    How beautiful New England of the US is, it’s on my bucket list, to visit, my husband who was born in Canada used to go to Cape Cod as a kid in summer holidays with his parents and siblings they would load up the Chevvy station wagon and drive all the way down from Toronto and have wonderful time, he tells me the time his dad managed to get a huge Crab and cook it, my husband said it was huge, I guess being teenagers back then they didn’t appreciate as they would today. My father in law who was an artist would sketch drawings of Cape Cod and we have them hanging in our home in Australia. Safe travels,

    • happytogether

      Hi Sandra, Thanks for the note!! You will love this place. It was such a special trip and we can’t wait to go back and do Maine and the Cape! Randy

  4. Mike Bevers

    Sounds like a great time. Hope to see you guys Saturday at the Annapolis boat show!

  5. Anne Ferguson

    Hi – my husband James and I just found you and have been catching up on all your blog posts and videos. How absolutely amazing to see all your adventures and the first hand knowledge we are getting about the Leopard brand is invaluable. We are South African, living in Old Greenwich, CT. We are making some future plans that include a Leopard Catamaran!! We are headed to the International Boat show in February and wondered if you will be there?
    Happy Holidays.
    Anne Ferguson