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If you're looking at doing the trip in early spring, I would just run west all the way up Long Island Sound from Rhode Island and down the East River and around and head back east to your inlet.
It would probably be faster to go south of Montauk and down the south shore of LI, but with a new-to-you used boat, the LI Sound route offers far more possibilities for ducking into port if you develop a problem. You're on your own on the outside route with really only one or two inlets you could run. If the weather is bad, you will also be much better off in LI Sound than the open Atlantic, even in a nice little Bertram..
*Your best bet is to cross from Pt Judith towards Little Gull Island( about 34 miles)*and head in toward Orient Point(total 42 miles).* Once inside you can go on the north side of Shelter Island around Greenport ( Good place to grab lunch)* to Cedar Beach and then south of Robbins Island to the Shinnecock Canal.* At the south end of the canal there are marinas*where you can get fuel if you need it.***After you leave Shinnecock, you have two options.* You can either run the ocean west along the south shore from Shinnecock Inet to Jones Inlet which is about*60 miles or if the weather is bad, you have the option to run the inside of the Great South Bay from Tiana Bay to Freeport.* The only down side to the bay is that you have some 5 MPH areas.* You're looking at about 150 mile trip that way.** Going through New York City you'll be looking at 190 mile with a trip through North Brothers Island (Rikers to the prisoners, also very rocky), Hell Gate and the East River( with tug and commercial traffic)*with no fuel stops available without going out of you way.* Once committed to Long Island Sound you'll have no shelter unless you duck into one of the harbors.* I've done both and if in your location I would opt for the Orient Point route because of the shelter it affords.* Hope this helps.********
Scali62 - 3/28/2005 9:56 AM You've got pretty big nuggets taking this trip this time of year 26'er {Bertram or not}. I would get a quote for delivery via land personally
Having stones is one thing, picking your days is another.* I've done those routes in a 23 Seabird and the last time with my 210 Striper.* I'll agree though this time of year isn't what I would even consider.
Hands down the Shinnie Canal route is the way to go.....yes the inside is shallow and has multiple no wake zones but is shorter and lots more forgiving as other have noted.............Are you new to the South Shore? Seems like a no brainer.........Hells Gate, better time it right if you choose that route.
Boats are out but if you take any spray its going to hurt! Water is 39-40 degrees? Be careful in the GSB, they had ice this year and that always moves things around.
I'll be running from Mass to Shinnecock the weekend of April 8th. On Friday if the weather permits. If it works for you, we could rendevous outside Buzzards somewhere. I'll take you as far as Shinnecock. I may run outside if the weather permits, but if need be I can guide you to the inside of the Shinnecock inlet. Let me know!
Is it the water temp or the seas that would keep you from doing this run at this time of year? J.
I wouldn't do it this time of year for a few reasons, weather, water temp, the 42 mile to Orient, the lack of traffic and limited facilities that are open.* With my current boat I would do it because of the range and twin engiines, but with a single, I'd give it serious thought.*
Rhode Island to Jones inlet, Long Island 
