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Re: Best Route from Mahattan to LI Sound
The East River is the way to go. Dangerous is a relative term. I would not take the trip up or down the East River casually, but it's very managable. You need to understand the currents and the timing and the Rules of the road and have a reliable engine. The entire transit takes about 2 hours or so from the Battery, ( to the Throgs Neck Bridge) with a favorable current, which you will need. The best time to leave the Battery is about two hours after low tide. ( at the battery). Eldridge tides and current tables, is a great book to have. But, you can obtain the information from a number of sources. The timing coming the other way is more focused on slack current at Hell Gate. If/when you do it for the first time, it might be a good idea to have an experienced hand onboard. Remember that the route takes you up the west side of Roosevelt Island past the UN. and not the opposite side. You can also pass between the Brother Islands rather than go around.
The Ocean route around long island on the other hand will take you 26 hours or more, and it's an exposed Ocean route with unfriendly inlets. So, major difference.
There's no viable route around the north end of Manhattan. The Hudson to the Harlem River to the East River, is not an option for sailboats.
When you're ready to do this trip, feel free to PM me and I can help you with the timing and give you some pointers.