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We will be sailing/motoring a 47-foot center cockpit ferro-cement ketch (Wind’s Call) with a beam of 13 ft and 6.5 ft draft and a Perkins naturally aspirated diesel from Annapolis, MD to Jonesport, Maine next month (July 2021). Her main mast is 59 ft and mizzen of 42 ft. We hope to have the captain plus 4 crew. Having spent the past 15 years sailing the Chesapeake Bay we need some recent information about routes, draft/ bridge clearances etc. We are considering heading north to the C & D canal to Cape May and then a straight shot to Jonesport. Any and all suggestions, information, cautions, GREATLY appreciated.

Rick & crew - Wind's Call
 

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I assume the C&D canal has the same specs for bridges as the ICW, IE 65' on any fixed bridges. Just look at a chart and confirm clearances.

Once you head down the Chesapeake and head north there's really no more bridges to worry about, they're all built with clearance for giant ships. UNLESS you decide to go up LI Sound and when transiting the East River you take the east side of Roosevelt Island, don't do that. But sailing through the city is fun.

Also there's not really too many options for routing. You go direct to Maine, south of Long Island or you take the scenic route through NYC and up LI Sound. Next choice, go through the Cape Cod Canal (shorter, faster but you have to time the currents) or around Cape Cod (but why would anyone do that?).
 

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Skpmac has pretty well summed it up. You will need a copy of Eldridge's for timing the tides & currents in the East River /Hell Gate in NYC, the Race or Plum Gut in Long Island Sound (though they're not as crucial) and for the Cape Cod Canal if you go that way.
 

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All of the information you’ve requested can easily be googled these days on your phone. There’s no need to purchase any special books for tides or bridge clearances unless you wish to spend more time in places, then a coastal cruising guide may come in handy. But even cruising guide books are becoming somewhat obsolete due to cheap and accurate apps available for phones and tablets like “Aqua Map.”

Simply download Aqua Map along with the US charts and you’ll be all set.
 

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While the forum/internet is a great place to get opinion and direction to authoritative material, I'd not take anonymous navigation answers as gospel (even though I agree with all that was posted above). These should all be easily reviewed and confirmed on the charts you plan to use for the voyage.

Going up LIS takes much longer, so it depends on what you want to do. Day hop and see the sights, or get there? When I take round trip cruises, I like to get there initially, then take my sweet time hopping back home.

As for the Cape Cod Canal, it saves significant distance. As said above, you must time the current. The only reason to go around the Cape, is if you plan to visit Nantucket. I've gone outside the Cape and it was remarkable the amount of lobster pots offshore.
 

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The Cape Cod canal can be done even if timed wrong when one travels against the current closer to the outer edge where the current isn’t as strong. It just takes an extra hour, but motoring with the current behind is definitely preferred and generally takes only about 45 minutes. Bridge and overhead wire clearance is 133 feet.
 

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Hmmm. The boat? Older diesel, ferrocement . . . do you know the boat well? Makes me wonder why include so much detail about the boat? Concerned? If so, hang inside and skip up the coast. From the Canal north you might get 25 miles offshore going toward Jonesport on a straight shot.
 
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