Sailing South Shore of Long Island in July

[Mahayana]

No better way to start a long term relationship than proving to the other party just how capable and responsible you are! Best of luck. I vote for the overnight, offshore to Sandy Hook route.

[eastendsailor]

Followed your journey from Montauk, where I go to surf in the summer and fall. Glad you made it and the wonky engine held up.

[tigerzilly]

Starting the relationship right. Now she calls me captain a-hole! We had a great trip!

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[Cadence]

Originally Posted by tigerzilly

Starting the relationship right. Now she calls me captain a-hole! We had a great trip!

Sent from my DROID RAZR HD using Cruisers Sailing Forum mobile app

That normally comes after saying "I do".

[kerrydeare]

Originally Posted by Scrimshaw4

Get the engine fixed ... NY harbor is not a good place to be without an engine ... I transit this area every year and would NEVER attempt it without a reliable working engine ...

I "third" this fellow sentiments. Forget Joseph Conrad, Lin and Larry, Slocum, and other ghosts of sailboat past). You really should not enter NY harbor these days without machinery and even AIS (although your screen will look lit a lit Christmas tree).

Having said that, there are a few "safe" (for NY) anchorages in the harbor that are accessible under sail (e.g., just behind Liberty Island, Gravesend, and so on), but NY harbor currents will beat most small sailboats on any given day.

If you survive (and it happens sometimes), you will be at best exhausted. At worst you will be run down by commercial traffic.