# Chesapeake to Western LI Sound



## chef2sail (Nov 27, 2007)

We are planning another trip to the LI sound this summer starting the 11 of July and lasting to the 26th. (We could extend anpther week if we want so give us plentry of recommendations) Anyonje who wants to do some of it is welcome. There are 2 boats from our club comming for some of the trip also.
Our wives are not keen on the cape May to Block island straight run yet so we will leave that for another year.

Comrades,

Last year we did this trip and went up the eastern side of the LI Sound and had a great time. We want to the the Conneticut/ RI side of the Sound this year.

We need some recommendations of places to anchor, anchor or moor and dingy in, get a slip for 2 days etc. If you give us a destination what is there that you can't miss seeing there.

Our trip will be From Rock Creek (Patapsco) to Reedy Island (Delaware River) to Cape May to Barnegat Inlet to Sandy Hook to Port Jefferson or somewhere on the Conneticut side. We have a week to see the sound and return to Sandy Hook.

Thanks for you help.

Dave


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## jasper (Dec 30, 2008)

was just looking for info on the same trip.. i am looking at a boat 
for sale down that way.. i will need to bring her home to NH.. 
said you went cape may to barnegut inlet.. would this be very 
hard for a single hander?


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## WanderingStar (Nov 12, 2008)

Check Duncan's Cruising Guide to New England. Detailed dscriptions of every harbor and anchorage, history and recommendations.


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## WanderingStar (Nov 12, 2008)

Lots of nice, walkable small towns on that shore. Enjoyed Westport, Milford, love Noank.


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## christyleigh (Dec 17, 2001)

jasper said:


> was just looking for info on the same trip.. i am looking at a boat for sale down that way.. i will need to bring her home to NH.. said you went cape may to barnegut inlet.. would this be very hard for a single hander?


 I did the trip in '05 when I bought my NC in Annapolis the same way Dave did. Barnegat is usually not recommended and although I had no problems.... surfing in on a quiet 'Good Day' with big fishing boats 'tailgaiting' me in was Uncomfortable. After Port Jeff I hopped over to Watch Hill, then to NGBay. Those stopovers worked out well for my wife and I doing Motor-Sailing Day Sails averaging 6kts. As for Single Handing my wife helps with docking, mooring, or anchoring other than that she just kicks back and enjoys the ride.


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## camaraderie (May 22, 2002)

There's nothing on the north side of the sound...Denby has ruined it all.


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## jasper (Dec 30, 2008)

yo,, I may join you with my single handed new/old boat.. sure would be 
easier with a couple of other boats along.. 

and the wait . ? no problem.. what is the hurry..


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## christyleigh (Dec 17, 2001)

chef2sail said:


> We need some recommendations of places to anchor, anchor or moor and dingy in, get a slip for 2 days etc. If you give us a destination what is there that you can't miss seeing there.


 The Mystic Seaport Museum in Mystic CT. This is not just a building but a whole seaport village from the last century with period people, buildings, boats, etc..... Essex CT is also a quaint village a couple miles up the CT River.


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## Bene505 (Jul 31, 2008)

Watch out for the Deleware Bay. If the wind is coming off the ocean, you get some good swells. Coupled with an outgoing tide, you get some steep waves.

Did a similar trip last July and had to motor into the wind at about 2.5 knots on our 50' Beneteau. Kept burying the bowrail into waves if we went any faster. No good anchorages in that area either.

Also make sure you have good charts, there are some shallow spots right next to the channel.

Now with those words of caution out of the way, enjoy the trip!!

Regards



chef2sail said:


> We are planning another trip to the LI sound this summer starting the 11 of July and lasting to the 26th. (We could extend anpther week if we want so give us plentry of recommendations) Anyonje who wants to do some of it is welcome. There are 2 boats from our club comming for some of the trip also.
> Our wives are not keen on the cape May to Block island straight run yet so we will leave that for another year.
> 
> Comrades,
> ...


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## SOUNDBOUNDER (Dec 16, 2008)

Agree!!! The Delaware is a desolate stretch.
Also, I think it is good to familiarize yourself with several of the inlets along the Jersey Shore. There are some stretches where they are few and far between.

Once you reach the Sound, A CRUISING GUIDE TO THE NEW ENGLAND COAST by Duncan, Fenn, & Ware is a very good source IMO.


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## SOUNDBOUNDER (Dec 16, 2008)

My recommendations for Long Island Sound would include:
Oyster Bay, NY
Northport, NY
Port Jefferson, NY
Rowayton
Norwalk Islands
Southport
Milford
Thimble Islands
Guilford
Noank
Stonington
Watch Hill, RI


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## jjablonowski (Aug 13, 2007)

Here's some interesting reading/planning from a local sailing couple: Coastal Boating .net, Long Island Sound Cruising Guide

Also try ActiveCaptain.com for a quick view of available facilities in the area.

And a note of possible caution. If you've never shot through Hell Gate, the narrowest part of NYC's East River that connects the Upper Bay with Long Island Sound, you might wanna research it. Tidal current is something to contend with, especially if your home sailing grounds are the Chesapeake and you're unaccustomed to five-six knots against you at times (or, with you, at other times).


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## SOUNDBOUNDER (Dec 16, 2008)

jjablonowski said:


> Here's some interesting reading/planning from a local sailing couple: Coastal Boating .net, Long Island Sound Cruising Guide
> 
> Also try ActiveCaptain.com for a quick view of available facilities in the area.
> 
> And a note of possible caution. If you've never shot through Hell Gate, the narrowest part of NYC's East River that connects the Upper Bay with Long Island Sound, you might wanna research it. Tidal current is something to contend with, especially if your home sailing grounds are the Chesapeake and you're unaccustomed to five-six knots against you at times (or, with you, at other times).


I have looked at the Coastal Boating site before. A lot of the info is wrong, or outdated. Its alright IMO for a general overview, but I get the impression that they didn't actually visit some of the places they claim to have.


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## chef2sail (Nov 27, 2007)

Yeah, gotta love Hell Gate...we ran with the tide last year and with rpm at 2000 normally giving us 5 knots speed over the ground we were flying at one point making 11.5 knots over the ground.

The 5 times X 2 that I have run the "gate" havent been bad as I was very cognizant of the tide situation.


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## danielgoldberg (Feb 9, 2008)

*That's my home turf*

First of all, get yourself the Embassy Guide for Long Island Sound, put out by Maptech. It's got tons and tons of information on everything about Long Island Sound, including harbor charts, recommendations on navigation, anchoring, dockage, places to go, things to see, where to eat and provision, etc.

Also get the Eldridge Tide Book. It's great for Hell Gate, and it's helpful for many other areas on Long Island Sound for currents. The reality is that if you are going to stay in western LIS, rather than the eastern end, current is not a big deal once you get through Hell Gate.

In terms of harbors that I would recommend, here are my thoughts, somewhat west to east:

1. Port Washington (Manhassett Bay). It's a very easy harbor to enter, and it's got a little bit of everything. You can anchor in protection (very good holding ground), you can pick up a mooring, or you can go dockside. Ashore, there are good restaurants (Louie's is a local favorite and a virtual landmark; it was featured in Meet the Parents), some shopping, and it's generally a nice town. You also can get fuel here.

2. City Island. This is an eclectic spot that struggles with whether it's part of the Bronx (it is) or is an island on Long Island Sound (it's that too). There are tons of restuarants of all sorts, everything from 4 star to sub-McDonald's. There's some marine supplies, funky shopping (not chic), a good ice cream parlor (Lickety Splits), and some cool stuff to see. It's not the best place to stay overnight if there's any weather. The harbor is exposed, and though you easily can take a mooring, you will roll and won't be uncomfortable. We go to City Island for day trips; tie to a mooring for a few hours, spend the day wandering around, and then head across the sound to Port Washington, about 4 miles away or so.

3. New Rochelle. This is a bit of a tough spot to get into, and depending on what you're into may not be worth it. There is no anchorage to speak of, and if you go you most likely will need to be dockside at one of the local marinas. There actually are two harbors (New Rochelle Harbor and Echo Bay), both of which require some attention to enter. I mention NewRoc, as it's known, because a few years ago they built something called NewRoc City, which essentially is an entertainment mall. It has everything from movies, to an arcade, to ice skating to restaurants. It's a bit of a long walk from the water, or a very short cab ride. If you have youngish kids, give this some thought, as it will be a good diversion for them. If not, you might want to take a pass. If you do go, and you go to New Rochelle Harbor, you can get fuel very easily.

4. Mamaroneck. We actually live here, and in my opinion the town does not get enough recognition as a place to visit by boat. All right at the head of the harbor you have restaurants, bars, a movie theater, shopping, supermarkets (a little further of a walk), marine supplies, ice cream parlor, beauty salons, and even a Shiatsu-Spa! The downside is that it's not the easiest harbor to find a place to stay. The town maintains a floating dock float in the harbor for guests (it's not tied to shore; it's like a mooring in the harbor, but it's a floating dock tied to two pilings). There is anchoring in the outer harbor, but that won't be so comfortable if there is any wind out of the south. There also is transient dockage at the Brewer's Marina.

5. Oyster Bay. This is a great harbor in a lot of respects. It's pretty, home to many celebs, very easy to enter, excellent anchoring in a number of different places, moorings available, and walking distance to town (where there are some restaurants and such). Most people go to Oyster Bay to enjoy the harbor and water itself. The fuel dock at Oyster Bay Marine Center generally is considered the best place to get fuel in the area; a huge floating dock, with a number of attendents to help, and it pumps high volume so you get good quality fuel.

6. Port Jefferson. Another harbor that's easy to enter with easy anchoring, moorings and dockage. The town is right at the head of the harbor, and it has everything you might need or want (save for repairs). It also has two very secluded places to stay where the scenery is great. Just to the east as you enter (to your port), there is something called Pirate's Cove, or sand city, depending on who you ask. It used to be a sand quarry. There are private moorings in there. There is no cost, and the rule is that you can pick one up, but if the owner shows up you might have to leave (in all our years of going there we've never had to leave). You then can go ashore and climb the bluffs for breathtaking views. Opposite Pirate's Cove, to the west after you enter the harbor (to your starboard), there is another area just as beautiful (I actually forget what it's called), but there are no moorings and you anchor.

7. Milford. There is no anchoring or mooring as a practical matter. You can anchor behind Charles Island, just outside the harbor, but it's not very comfortable in any wind at all. If you go to Milford, you go dockside. There are a number of places that are very nice, and they all are walking/dinking distance to town.

Those pretty much are the highlights for western Long Island Sound. There's much more to the east, and there's even more in the western Sound that I haven't covered. I strongly urge you to get that Embassy Guide, as it will tell you everything about every harbor. It's a great place to cruise because there are so many places to go, all within a day sail of each other.

If you have any questions or want some more local knowledge, feel free to PM me.


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## SOUNDBOUNDER (Dec 16, 2008)

DanielGoldberg,
Good post! I disagree with a few things however.

1- New Rochelle is not geared towards transients. Also, everything there involves a cab ride.

2- Port Washington/Manhasset Bay is a great place. I have anchored and grabbed a mooring at several of the clubs there. Very nice. Louies has become overpriced with ordinary food IMO. Yes it is a landmark, but it is not what it used to be.

3- The sand hole in Port Jefferson is also called Mt Misery Cove. The anchorage to the west is the approach to Conscience Bay.

4-City Island has really gone downhill in the past few years. Many of the quirky shops and antique stores have disappeared one by one. There has also been a significant number of fires there in the past few years.
A yacht club, the maritime museum, a boatyard, a block of stores etc have all burned in recent years. Many of the restaurants are owned by the same corporation, and while I am certainly not a restaurant critic, none of them IMO are four stars.

5-I think there are better alternatives to spending $45 on an Embassy Guide. They seem to be poorly written, and are little more than shopping guides that frame the text around their advertisers. IMO, Waterway Guide, and A Cruising Guide To The New England Coast are better resources.

6- I agree with you about Mamaroneck. It is a good harbor, and it is great that the main street (Mamaroneck Ave) of town meets the harbor. There is also the park, as well as a really cool marine hardware store. I would go there more often if it was more transient accessible.


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## danielgoldberg (Feb 9, 2008)

SB, thanks for your post.

You make a few good points, but allow me to retort  :

1. We used to live on Davenport Neck, and dock our boat at our house there, so we know that area very well. You can walk from Davenport neck to New Roc City. It's not a short walk, but it is walkable. And if you are cruising and looking for a longer walk to get some exercise (that's what we do anyway), it's very doable. In Echo Bay, Dudley's and On the Waterfront are right on the harbor. There are several marinas in Davenport Creek that offer transient dockage (Imperial, Castaways, Wright Island and the New York Athletic Club, if you have reciprocity).

2. Louie's definitely is not the greasy spoon it once was, and I agree with you that overall I preferred the old place. BUT, the bar is much nicer now, and the outdoor seating overlooking the harbor is very nice. The food definitely has gone up in price and the same cannot be said of the quality (it's not bad food, but it is overpriced). Still, you can't go to Port Washington and not stop in at Louie's, at least for a Margarita while you watch the fleet come in.

3. Thanks very much for the clarification. I never can remember Conscience Bay for some reason. To me it always will be "that nice anchorage to the west of the entrance."

4. I'm curious about your comments on City Island. When is the last time you were there? It actually is undergoing a resurgence. There's new construction, new shops and stores, and even a West Marine Express. On your other point, it has never been ritzy, but that's part of what makes the place City Island (a cross between the Bronx and a yachting destination).

5. I guess that's why they make both chocolate and vanilla ice cream! I just love the Embassy Guides.

6. Yup, Mamaroneck does a terrible job of letting the world know about the transient options, and it is true there are not all that many. That said, if you want to come over on any given weekend, shoot me an email, PM or something and I'll guide you to a place. Keep in mind that town float in the west basin; it's always available and I rarely, RARELY, see a boat on it. 

Where is your home port? Maybe I'll see you on the Sound this coming season.


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## SOUNDBOUNDER (Dec 16, 2008)

I kept my boat in City Island for about 8 years (until 2006), and I have friends there. In fact I was there last week. The West Marine is out of business. I think it closed sometime this past year. I think the resurgence on City Island ended a few years ago. In the past two or three years, numerous places have closed or burned down.

I actually have had the boat up in eastern CT for the past two years, for a change of pace. But I will eventually be back in the western part of the Sound.
Eventually I will take you up on your offer. Thanks.

As for Mamaroneck, I didn't even know the town float was in the west basin. I remember years ago they let us tie up for a couple of hours at the dock right next to the boat ramp on Harbor Island. We went up to Brewers, hit a few stores, then had some lunch and a couple of beers.


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## jasper (Dec 30, 2008)

did a quick ebay look see, and there are embassy guides there for 
cheap cheap.. not sure today,, but usually anytime.


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## jasper (Dec 30, 2008)

I'm reading this and thinking "burning" "fires" ... 

I am from the great white north,, up there,, down east.. 

The only burning that happens in in the wood stove.. 

What's up with you NY'ers? Is it a war zone ?


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## SOUNDBOUNDER (Dec 16, 2008)

jasper said:


> I'm reading this and thinking "burning" "fires" ...
> 
> I am from the great white north,, up there,, down east..
> 
> ...


YES!!!
Your mindless provincial rants are 100% accurate.
You are morally superior, and we are ethically substandard.
Not only are there fires, beheadings and rapes are an ordinary event too.My galley serves as a crack den,and the head is a cheap brothel. It is part of our godless agenda. In fact, the rescue of the plane crash passengers last week involved several gang fights. 
In fact Maine never has fires. I wonder why they even bother having firehouses.
Maybe it is because of this:
MaineToday.com | News Update: York home damaged by fire

MyFox Maine | Shipyard Fire

Teach me more about this provincialism you subscribe to.


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## CalebD (Jan 11, 2008)

We even get an occasional plane dropping out of the sky too. So look forward, look aft and look up to make sure you are in the clear.
Most municipalities do not allow 'open' fires on the beaches. There are only a few places one can get away with this kind of activity, however fun and illegal.


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## chef2sail (Nov 27, 2007)

Dan and Sounder great information. I have found a cheap copy of Embassy. I have a couple of logistical questions.

I am now looking to try and maximize my first day push up the Sound from Atlantic Highlands. The day I am leaving there the slack before flood tide at Hells Gate is 9 AM. So we will probably leave the Highlands earlier at 6 AM where the flood is earlier and ride it through the East River. This should give us a 3 hour ride from the Battery to the Throgs Neck and the entrance of the LI Sound at about 11-12 AM. We are thinking Greenwich is were we should plan to land which is about 2=-25 miles or about 5 hours (5 knot average speed). What is Greenwich like? Our next stop Would be Branford which is about 40 miles or 8 hours. What is Branford like. From there50 Miles to the detinations end at Mystic. We were planning on staying 3 days and joininig the Seaport ( you get a night free plus addmittance for members) and docking there. Does this seem reasonable or doable? Two 40-50 mile legs from Greenwhich to Mystic?

The trip back would see us stopping in The Thimbles.....Mamaroneck...Then down the East River to Atlantic Highlands. How far from Mamaroneck to the Throgs Neck? I am estimating 12- 15 miles and about 3 hours at 5 knots.


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## SOUNDBOUNDER (Dec 16, 2008)

Chef,
I have sailed the entire distance of the Sound in two days (daylight), so yes that is doable.

A question,....do you plan on anchoring, grabbing a mooring, or docking when you stop? There are some good anchorages in Greenwich, but transient dock space can be hard to find. Are you a member of a yacht club????


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## danielgoldberg (Feb 9, 2008)

You definitely can make that trip up the Sound during daylight in two days, as SB says.

Why did you select Greenwich, might I ask? If it's just because it seemed like the right distance, I would consider Oyster Bay instead. Greenwich is just not the best place to anchor. There are spots, but it's rocky and you need to pick your way in. OB, on the other hand, is incredibly easy to enter, day or night, is only a few miles away from Greenwich, and you can anchor or grab a mooring quite easily.

Branford is fine, and there is a nice Brewer's Marina in there (Bruce & Johnson's Brewer's Marina it's called, or something like that). Again, did you pick Branford just to pick a spot? If so, consider Westbrook. The Brewer's marina there is a little easier, and you are that much closer to Mystic.

Mystic is great, and staying at the Seaport is lots of fun too (you get to wander the grounds after closing, among other things, and downtown Mystic also is worth the time). Note two things. First, there are no floating docks at the Seaport, and you may end up tying to a stone seawall. They provide fender boards and help you tie up, so don't sweat it, just be aware of it. Second, in order to get that far north up the Mystic River, you need to deal with two opening bridges. The first is easy, the second can be a pain. The first is a railroad bridge that remains open except when a train is coming. It's only caught me a couple of times over the years, but even then there is enough room in the river to hold station and wait for the opening. The next bridge, however, can be painful. It opens on a schedule (I can't remember it exactly, but call in advance and they'll tell it to you, or look it up online, or the Embassy Guide might even have it). There, it tends to be windy for reasons that escape me. It's one of those bizarre places where there always seems to be wind for no good reason. Plus, there is decent current, so holding station sometimes is not so easy. If there are not too many other boats waiting, there is room to simply circle around while you wait. Or, on your starboard side as you approach the bridge there is a public dock (non-floating) to which you can tie while you wait for the bridge opening, but you are not permitted to leave your boat. Note that if you go during a busy time it is quite possible that there will be several boats on the dock already. I don't mean to scare you with this, as it all is very doable, you just should be prepared. 

In terms of your return trip, again, the Thimbles? That's all granite there, and you really can't anchor easily, there is no place to tie up, and if you make a mistake, it won't be a soft grounding. For your return, I would consider day one to Milford, day 2 to Mamaroneck or Oyster Bay again, and then on into the city. Yes, you can make the Throgs Neck Bridge in three hours from Mamaroneck, and likely less.

In terms of timing the tide to come up here, the general rule is to hit the Battery at slack before flood to come up through the East River and Hell Gate. So give yourself whatever time you need to get to the Battery for that. Better a little late than a little early (if you're a touch late the tide will be stronger, but it'll be with you, so that's not so bad). 

Hope you enjoy the trip, and don't hesitate to ask additional questions.


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## SOUNDBOUNDER (Dec 16, 2008)

There are plenty of moorings available in the Thimbles between Money and West Crib Island. The Pine Orchard Yacht & Country Club has many 400 and 500 lb moorings that are free, providing they are not using them. If it is a weekday, there will be no one on them. If they are being used, many boats often leave before sundown.
I have done this 4 times and never had trouble finding a mooring.
The Thimbles are really a beautiful spot.


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## xxuxx (Nov 14, 2008)

*Tobay.................*

When I was younger, I used to dig for steamers(ipswich clams) in TOBAY, do you know if they still dig for them? I love oyster bay and haven't been back in over 30 yrs.....I wonder???


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## danielgoldberg (Feb 9, 2008)

SOUNDBOUNDER said:


> There are plenty of moorings available in the Thimbles between Money and West Crib Island. The Pine Orchard Yacht & Country Club has many 400 and 500 lb moorings that are free, providing they are not using them. If it is a weekday, there will be no one on them. If they are being used, many boats often leave before sundown.
> I have done this 4 times and never had trouble finding a mooring.
> The Thimbles are really a beautiful spot.


I've never seen those moorings. Learn something new every day I guess! I'm going to check that out.


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## chef2sail (Nov 27, 2007)

Sounder...yes I am a memeber of the Maryland Yacht Club so I may look for clubs which will give reciprocity.

Dan...good comments. I looked at Oyster Bay as well as Huntington Bay..they both look like great spots. 

We will choose to anchor, mooor or dock depending on what we think is best when we choose the final destinations. Thanks for the info on Mystic and the bridges. Thats second bridge current is a doozy you are right. I want to stay in Mystic for 3 days so it is the only place I am sure we will take a slip. I prefer to take a mooring over anchoring. Your report on Thimbles is well taken. I wasnt aware that Greenwhich was that difficult an entry.

Again thanks for all your help. the comments are appreciated and helpfull in helping me plan.

Dave


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## mrwuffles (Sep 9, 2008)

Huntington is great and well protected. Plenty of anchorages and places to get fuel and pump out.


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## CalebD (Jan 11, 2008)

Chef, 
I know that you have been up and down the East River before but for you to take 3 hours from the Battery to the Throgg's Neck Bridge is a bit un-realistic IMHO. My charts show this to be a distance of just under 15 nm which if you actually have the current with you (and you should time it so that you do), you will be making a speed over ground of way better then 5 nm/hour. Perhaps you meant 3 hours from Atlantic Highlands to Throgg's Neck which seems a bit more ambitious but realistic to me (if the currents are in your favor). 
On one of my trips around Manhattan, coming down the Hudson and up the East River on a friends Mac 26S we hit the East River a little early (slack at the Bowery). We got as far as the Williamburg Bridge where we met the still ebbing current and decided not to fire up the small 8 HP motor so we waited about an hour until the current turned and helped push us through the East River and one of the worst electrical storms I have witnessed as we passed LaGuardia Airport. Once we passed the Throgg's Neck the sky became blue again instead of sickly yellow/green.
The Eldridge Tide & Pilot gives you some excellent current charts for this area that we just did not pay enough attention to. As you know, you can expect to cover nearly 10 nm/hr with the current going with you at full(ish) strength. 
Once past the Throgg's Neck you could reach Port Jefferson if the flood in the East River was early enough. OB or Huntington are more manageable though.
Sounds like fun.


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