Re: Sailing a boat from New London, CT to NJ
Going South of Long Island offers few bail out ports. I would head West through the Sound, down the East River and onward. You will have to time the currents in Hell's Gate and the East river, but its done all the time. Sailing past Manhattan is a trip!
The delivery would be a ton of fun, but very unlikely to work precisely. You'll have to be prepared to lay up for weather, etc. If you just want to get her home, a boat of that size is among the easiest to deliver on a trailer. The downside is, depending on your purchase budget, it could be a significant percent of the purchase price.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.