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Discussion Starter #1 (Edited)
Circumnavigation of Long Island Sound

I am planning my first longish trip on my boat (a 25' Seaward with an 8HP outboard) and am thinking of bouncing up the Connecticut coast eventually reaching Block Island, then going along the north shore of Long Island on the return trip to Manhasset Bay.

Question is;Would the two weeks between Mother's Day and Memorial Day be a reasonable window? I'll be mostly solo, maybe my son and his gf on a weekend. A mix of anchoring out and marina stops along the way are planned.

Boat's to be fitted out with new VHF and masthead antenna, autopilot jacklines and harness. I might get a Spot as well.

Mike
 

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Sure, two weeks is an adequate amount of time.
But you should put together an itinerary of where you want to visit.
Keep in mind you will want to stay more than an overnight at some places, plus weather may hold you back.
Also, "bouncing up the coast" will need to include some days where you make some significant distance. You don't need to stick to the itinerary, but at least it will provide an idea.


Plus, the Long Island side is a bit sparse for ports east of Port Jefferson.
 

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Discussion Starter #3
Matthew,
Definitely some significant distances. I was thinking of Block Island - Greenport on the return leg, then a very full day Greenport - Mt Sinal or Pt Jeff, with an invigorating but well-timed trip thru The Gut. :eek:
On the outbound route, I intend to do some meandering. I'm thinking of a side trip up the Connecticut River to spend the night in Selden Cove. Longest continuous trip I've done so far (in this boat) is Oyster Bay-Manhasset, so it should be quite the adventure.
Mike
 

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Also, when making up your itinerary, make sure you note the approaches to the harbors between, in case an emergency or weather forces you to take shelter at them. Having a page with notes about the navigation requirements for each harbor, with information regarding ranges, buoys, courses, radio frequencies, etc, would be a good idea. This makes it much safer and easier if an emergency or bad weather forces you to have to make an unplanned stop, since you won't have to look all that stuff up on the fly.
 

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Sailing Dog makes an excellent point, especially since this is your first time, and you will be solo.
Become familiar with the harbors in between. For example, if you are sailing from the Thimble Islands to the CT River, you should familiarize yourself with Westbrook and Clinton Harbor for a back up plan.

When I had my Bristol 24, I made a similar trip by myself (minus Block Island) from City Island to Stonington, and back. A thunderstorm was building one day and I couldn't reach Black Rock. I ended up sailing in to Southport, which is a tricky harbor if one is unfamiliar with it.
 

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Matthew,
Definitely some significant distances. I was thinking of Block Island - Greenport on the return leg, then a very full day Greenport - Mt Sinal or Pt Jeff, with an invigorating but well-timed trip thru The Gut. :eek:
On the outbound route, I intend to do some meandering. I'm thinking of a side trip up the Connecticut River to spend the night in Selden Cove. Longest continuous trip I've done so far (in this boat) is Oyster Bay-Manhasset, so it should be quite the adventure.
Mike
I haven't been to Selden Cove, but I hear it is beautiful. Hamburg Cove is a nice spot as well.
 

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Mike,
That sounds like a fun and adventurous trip you are planning.
I found this website recently which details places of interest in the Peconic Bays/Greenport etc. There are descriptions of each tricky channel.
The Boater's Cruising Guide for Eastern Long Island, NY
Don't forget about Mattituck which is between Greenport and Port Jeff. It is a bit tricky getting into but it is there and could be shelter if needed.
The time you suggest taking this trip makes perfect sense if the weather cooperates. I would think that Block Island and points way east on LI would not be overly crowded with 'summer people'.
 

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Discussion Starter #8
sailingdog, "sound" advise (sorry for the pun). I've been spending the winter pouring over charts and Google Earth. Going to have lot's of alternates at hand.

Don't know if I'll make it out to Block Is. I'll go for it if my son crews with me for a couple of days. As far as Mattituck, I was scouting the inlet just a few weeks ago while having lunch at the restaurant there. Shouldn't be a problem, unless of course it's foggy and there's a line of 50' canyon boats on their way out! My biggest friend will be the tide books. I don't want to fight the race coming or going. Hanging out in the Peconics area is also a possibility. I'll look into that guide.

Thanks for the tips!
Mike
 

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not Sully or Dandelion
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Good luck with your trip man. If things get boring you could always go through Plum Gut at the "wrong time".

If you stop at PJ Harbor I will buy you a brewskie or two.

Have fun

Paul
 

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Mattituck isn't that bad unless of course there is a lot of large boat traffic, but me and my dad pulled into it one night with out a problem. The trickiest part was seeing where the channel turned because it was pitch black.
 

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When I was on a leg from Mt. Sinai towards Orient, and sailing past Mattituck, I watched for it and found it remarkably hard to see the entrance. I knew where it ought to have been from the GPS, but as far as visual cues, they were almost nonexistent, and it was a moderately clear day. On the North Shore of Long Island, its quite a long leg from Mt. Sinai to Orient, and no harbors of refuge except Mattituck. Also, watch the current charts and use Eldridges. There is a huge difference in time made with a favorable current versus an opposing one.
 

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Matthew,
Definitely some significant distances. I was thinking of Block Island - Greenport on the return leg, then a very full day Greenport - Mt Sinal or Pt Jeff, with an invigorating but well-timed trip thru The Gut. :eek:
On the outbound route, I intend to do some meandering. I'm thinking of a side trip up the Connecticut River to spend the night in Selden Cove. Longest continuous trip I've done so far (in this boat) is Oyster Bay-Manhasset, so it should be quite the adventure.
Mike
An overnight in Seldon's Creek would by pleasent and quite doable. Unless you draw less than 2 ft you won't be able to get into the cove. There is also (free) campsites available on Seldon's Island if you anchor above Eustasia Island and take the tender to the Island.
 

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Discussion Starter #13
Eldridge is my number one reference! Even in the western end of the Sound, I try to time trips with the flow at "The Race". Even if I get up to 5 kts with the wind, you take a 20% hit with an opposing 1kt current. And 5kts can be tough in a small boat with light winds!

BTW, official draft is 25". I haven't taken advantage of the shallow draft yet, except to spend an inordinate amount of time sailing laterally :eek:. Which means, really, is that I have yet to touch bottom ;)

Mike
 

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You can do it, and have fun. Years ago I cruised a twenty foot sloop from West Babylon to Port Jeff, then back as far as Port Washington before I ran out of time and wind. (I had no engine) That was in May and early June. Just remember a good sleeping bag and warm clothing. The water is still quite cold then, nights are cool.
 

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Discussion Starter #15
John,
No engine, way to go! Time I'm going to have. I have 3 more days, then a 30-year career is over. Going to sail my a$$ off until I have to go make some money. Kinda liberating!
Mike
 

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You'll need Eldridge... :) it's a necessity IMHO for anyone sailing in these waters.
 

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Mike, another vote for Eldridge--unless you have other current charts and tables. How feasible the trip is will depend on the weather. For instance, Block Is. would be a hard run for you if there was heavy fog. And 25' can feel like a mixmaster if there are small craft warnings and sloppy seas.

But 25' is perfectly adequate for most of the Sound most of the time, even if you have to change plans on the fly, it should be a blast. Oddly enough, sometimes you'll get bugs even in the middle of the sound--so add bug repellant to the stores list!
 

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Amen. Looking forward to the same scenario. I could retire now, if I left LI. This last snow had Jane suggesting we move south now......
Probably a few more years.
 
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