Our circumnavigation of Long Island
Lets see if I can make a long story as short as possible! Our circumnavigation of Long Island trip lasted two weeks. We sailed the ocean (south) side to Block Island and came home via Long Island Sound. I can give you some information on places to stop in the sound and approximate time it took us to get between each. We sailed (motored when the wind died) from Cheesequake Creek in Raritan Bay to Block Island in approximately 28 hours, non-stop. It was very foggy after dark so the trip was somewhat trying. Our first overnight trip, and only the compass and GPS to help us thought the fog, as we have no radar. Block Island was fun, we stayed for two nights. We arrived on a Sunday, so a lot of boats were leaving and we got a mooring fairly close to shore. We rented a moped for ½ day and walked the rest of the time (recommend a moped to see both the north and south lights). Good places to eat and nice beaches, shops, etc. From there we sailed (17nm) to Lake Montauk, maybe 4 hrs. Stayed for two days. We anchored just after the channel ends and the "Lake" opens up, just south of Star Island. It is VERY shallow in places, so keep the chart nearby. Then on to Greenport, that was about 5 hours (20nm). It was an uphill windy, misty, cold day and rained that night. We anchored in Dering Harbor that night and got a mooring the next day. We took the ferry to Greenport, rented a car and did some wine touring. For some reason the rest of that day is a little unclear to me....Oh yeah, I remember trying to get a case and ½ of wine back to the boat in a Walker Bay, not an easy task, but doable. Then on (35nm) to the Thimbles, a good days sail. You MUST time your passage through Plum Gut or it will take you a lot longer to get there. We picked up a friends mooring there. Anchoring looked a little difficult. Took a launch, The Charley Moore, to shore to meet them for dinner. Next stop, Port Jefferson (20nm). We anchored in a wide-open area near shore in the middle of all of the mooring balls. After we anchored we rowed ashore to eat lunch and do some shopping, we came back and some guy from the yacht club came by and told us "you have been bad, you anchored in the mooring field.” He said that the anchoring area was all the way in the back (north) of the moorings, at least a mile from town. When we asked about the open area, he said, “We are just getting ready to put moorings in this area and you are in our way.” Strangely there was no evidence of any moorings, or people to place them. Nor were there any indicators prohibiting anchoring in the area. We moved up by the Spoil Area for the night. Next day was on to The Sand Hole at Lloyds point (20nm). This is a great little hole to anchor in, but you must be very careful entering and wait for the tide depending on your draft. We saw guy in a 35-40 footer get stuck on the sand on a falling tide and didn't get off (even with the help of the Coast Guard) for 6 hours until high tide. From there we were planning on stopping off at City Island, but decided to try Manhasset Bay as we hadn't anchored in there before. A lot of boats are moored in that area and not a lot of room, but it was a weekday so we found a spot. Holding, at least were we were, was tricky. I think it took 4 or 5 tries and moving around a bit to get a good grip. The next day we planned for our arrival at East River so that the flow would be in our favor. Flushed through with no problems and continued on to Sandy Hook. Then back to the dock and back to reality. In addition to the above, We would recommend both the east and west sides of City Island and have spent several nights in Northport Bay, just east of West Beach. Both of these are easily approached in the dark. Also, Sheffield Island (one of the Norwalk Islands) makes a nice anchorage near Norwalk Ct. Be careful in the west end of the sound, Stepping Stones didn’t get its name because they were under water.