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Sailing Long Island Sound

The joys of our journey down Long Island Sound were much more than we expected.  There were so many places to choose from, but with only so much time, we decided to visit:

  • Shelter Island
  • Plum Gut Anchorage Cut
  • Greenport
  • Oyster Bay
  • Port Washington

WATCH our Video: Long Island Sound sailing

SAILING LONG ISLAND SOUND - Shelter Island, Plum Gut, Greenport, Oyster Bay, Port Washington

First Stop – Shelter Island – 36.8miles – aug20-21

Anchored in Coecles Harbor – so quiet!  (Except on weekends).  (Pronounced Cockles)

Marina has Bike Rentals !  We biked around the island one day.  Great produce educational facility on the island and they run a market that has just enough variety for a light restocking of provisions.

In the center of the harbor is an island cabin.  Originally named Cedar Island, Taylor’s Island is now a Shelter Island Town park. The unique house originally built at the turn of the 20th century, serves as a landmark for vessels navigating Coecles Harbor. The Island was bulkheaded and filled during the 1930’s and the log cabin was expanded in the 1940s. Deeded to the town by S. Gregory Taylor, the Town took possession of the Island in 1998. This site is in the process of being placed on the National Register of Historic Places. You are invited to go ashore here to rest or have a picnic. 

Congdon Creek is a nice dinghy trip as well.

Next stop – Greenport – .8miles – aug22

Stopped here long enough to provision at the nearby IGA and walk around town.  Lots of beach style boutiques and ice cream shops.  Nearby State Park has a super Long Beach that reaches to Plum Cut.  On the back side of that beach, you can anchor easily to the right of the breakwater.  Unique lighthouse in the old victorian “cottage” style. And wineries, lots of wineries.

Our favorite stop – Oyster Bay – 71 miles – aug 23

We didn’t get to experience all of Oyster Bay, so we will be back! This was Teddy Roosevelt’s hangout and the official “summer White House” for execs and staff, Sagamore, which we toured is a National Park. We also visited Wild Honey restaurant – exquisite meals in a historic hotel Teddy used to stay in. Next time, we will visit

  • Planting Fields Arboretum State Park – 49 acres including a 1918 65 room Tudor mansion.  
  • 20th century cycles museum
  • 8 beaches.  Wildlife Marsh Sanctuary. 
  • Settled in 1653, famous for shipbuilding,  spy activity,  
  • Octagon Hotel (now being restored)
  • Fish Hatchery and educational center

Last Stop before New York City – Port Washington – 21 miles – Aug 25-26

  • Stayed at Safe Harbor Capri Marina – great stop!
  • Easy water access to many fine restaurants
  • Washed the boat
  • Found a dress for my son’s wedding
  • Battery blew up – literally – when Stephen started the engine. Never found out why. 
  • Jennifer Bell (Stephen’s sister) arrived for our sailing adventure through New York City.