Trip planning LI sound

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Unclematt

Senior Member
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Apr 9, 2020
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318
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United States
Vessel Name
Seaview
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Sundowner 32
I have never cruised down LI sound and want to start making a plan A, B & C. In June I start my solo Loop from Narragansett Bay. I want to know what anchorages are good as I make my way to the Hudson. My first night will be on Block Island, I plan to run about 40 to 50 miles per travel day. What do you recommend? I will sight see on my way back. Thanks
 
I have never cruised down LI sound and want to start making a plan A, B & C. In June I start my solo Loop from Narragansett Bay. I want to know what anchorages are good as I make my way to the Hudson. My first night will be on Block Island, I plan to run about 40 to 50 miles per travel day. What do you recommend? I will sight see on my way back. Thanks

There are a few things to consider. I'm assuming you've been to Block Island before? How many days do you want to spend going from Block to the Hudson? If you plan to run 40-50 miles per day you won't see a lot of Long Island Sound, just a couple stops. Another question is do you have a preference to be in the north (CT) or south (NY) side of the sound? (wind and weather could influence this. Also there is a decent east/west tidal current in the sound that is worth timing if you can). Do you want to visit any places like Montauk and Shelter Island, or just get from Block to the Hudson directly? Do you plan to anchor or stop at marinas? Are you planning to travel up the Hudson and do you want to spend any time in NYC and travel around Manhattan or cut across via the Harlem river? Where is your final destination before you return and what are you planning for the total length of time for the trip?

Sorry for all the questions instead of answers, but if you can narrow your focus a bit it would save some time suggesting places that you are not interested in.
 
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I grew up on the sound.

On LI side Sag Harbor/Greenport/Port Jefferson/Centerport are great stopovers for access for activities.

Reserve early...expect crowds and less-than-competent operators on the weekends.
 
I grew up on the sound.

On LI side Sag Harbor/Greenport/Port Jefferson/Centerport are great stopovers for access for activities.

Reserve early...expect crowds and less-than-competent operators on the weekends.

No Mattituck? Depends on his agenda really which is why I asked what I did. I grew up in CT, boating on the sound for many years. Lots of options. Personally I think I would try to get an idea of what the various harbors are like and plan on the fly based on weather and other factors.
 
I agree with Osprey, the south side is nicer as there are good harbors for anchoring. As a solo, it is much easier to anchor out than to get into a slip. I would also add Oyster Bay to his list of nice anchorages. Needless to say, one should time the passages thru the Race and the East River. This can be a nice section of your trip. Take your time on the Loop and enjoy. It took us two years and we had plenty of time for fun. Also try and find some folks who will want to go with you on part of the Loop. Two folks makes it a lot easier and then there is someone to get you a drink.
 
I agree with Osprey, the south side is nicer as there are good harbors for anchoring. As a solo, it is much easier to anchor out than to get into a slip. I would also add Oyster Bay to his list of nice anchorages. Needless to say, one should time the passages thru the Race and the East River. This can be a nice section of your trip. Take your time on the Loop and enjoy. It took us two years and we had plenty of time for fun. Also try and find some folks who will want to go with you on part of the Loop. Two folks makes it a lot easier and then there is someone to get you a drink.

It's not clear from the OP, is he doing "The Loop" or a loop of Long Island Sound from RI? I assumed the latter, but I've been wrong before.
 
Doh!

Yup Mattituck is a great town and a cool passage from the sound.

If you want anchorages...Coecles Harbor in Shelter Island, Port Jefferson Bluffs (just as you enter) Eatons Neck/Sand City (Huntington Bay), Oyster Bay. Manhasset is a great jump off point for East River.

I love Watch Hill, Mystic and Essex on the North side.
 
Doh!

Yup Mattituck is a great town and a cool passage from the sound.

If you want anchorages...Coecles Harbor in Shelter Island, Port Jefferson Bluffs (just as you enter) Eatons Neck/Sand City (Huntington Bay), Oyster Bay. Manhasset is a great jump off point for East River.

I love Watch Hill, Mystic and Essex on the North side.

All good spots. Clinton is also good on the North side as well as Branford, but still waiting to hear if the OP prefers marinas or anchorages. The Thimbles are cool but I'd hesitate to reccomend a night there if you're not familiar and it can be rolly depending on the wind/waves.
 
If it’s not a sightseeing trip out is there a reason for stopping at Block? If it were me leaving Swansea heading for the Hudson, I’d go thru Watch Hill Passage, anchor behind Fishers Island and break out a can of Fishers Island Lemonade to celebrate. Then about 55 nm or so is Port Jefferson to anchor. Then 30+ nm to Manhasset, Little Neck or Little Bay to anchor. Next day time it for Hell Gate if you want, East River and around the Battery.
 
If it’s not a sightseeing trip out is there a reason for stopping at Block? If it were me leaving Swansea heading for the Hudson, I’d go thru Watch Hill Passage, anchor behind Fishers Island and break out a can of Fishers Island Lemonade to celebrate. Then about 55 nm or so is Port Jefferson to anchor. Then 30+ nm to Manhasset, Little Neck or Little Bay to anchor. Next day time it for Hell Gate if you want, East River and around the Battery.

I agree. I'm not a big fan of Block either. People tend to love it or hate it there. Maybe he's never been, who knows. Also, PJ to NYC is doable in a day, depending again on his agenda and the timing of the tides.
 
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You guys are great. I am doing the whole loop with my dog starting around June 1st. I will have some guests along the way so they say. Block Island was just based on miles no real desire to go back there. I am all about anchoring and using my dingy. I will mostly do marinas to provision, fuel, pump out, refill water and do laundry. If there is something I decide to do along the way I can plan to stay weather it be marina, mooring or on anchor. I would rather go down the LI side to get to the Hudson. I want to anchor out at the Statue of liberty before heading up the river. Sight seeing time going will depend on how much extra time I have from when I leave home to my first marina stop which is Shady Harbor. I made reservations and plan to meet fellow loopers for the pig roast which I was told is 6/11. I have been a boater all my life mostly Narragansett Bay. Three years ago I moved up to a trawler for extended retirement travels. My wife does not share my extended travel plans and is fine with my desire to travel. She says she will do bits and pieces which remains to be seen.
 
Agree with b. Also find block not worth it and can be most unpleasant between unskilled discourteous operators and Hondas placed on deck running all night. Bottom chewed up. People don’t know how to anchor so drag. Personally prefer the Connecticut side. Would add stonington to your list. A delightful town with great architecture and restaurants if you’re interested. Usually hang around city island if timing the ‘gate. Lots of places to anchor even if outside designated fields.
Of course pick the side which won’t put you in a lee shore if it’s sloppy. Both sides are good but for stops find the Connecticut side more interesting. If you stop at port Judith go as far inland as draft permits. Beautiful area for a good nights sleep. If just making time anchor inside the breakwater. Don’t enter the harbor. The breakwater works well and there’s little roll except if it’s blowing dogs off their chains. Run just outside the shipping channels if it’s nice and you want to make time.
 
I recommend the Thimble Islands off of Branford, CT. It’s about 50 miles from BI. There are several anchoring areas. If you do stop there, I recommend using the main channel beginning just west of Outer Island. The entire west side of the channel is the easiest anchoring and is protected by islands on either side. There’s a ferry service if you don’t have a dinghy to get ashore with. Alternatively, you could go farther west an anchor in Branford Harbor. There is no ferry service, but there is a dinghy dock just inside the Branford River on the north side. Both locations have near by parks and pleasant walking areas.
 
Anchoring. In. Block. Island. Sucks.

Deep and poor holding ground. Moorings are first come first serve. However it is a neat place to visit during the week in June, or better yet September, when the Budweiser fueled thrum is mostly absent.
 
I boated in LI Sound for 30 years and also cruised to and up the Hudson several times.
Block is worth a stay. Go across the channel from the town moorings and anchor in 6 feet of water. Holding ground is sand, not the greatest but I never dragged there. Set the hook properly and you'll stay.
I always liked stopping in Mattituck inlet on the LI side. Nice but small anchoring basin at the end of the channel. Public pump out at the sound end of the channel.
Port Washington has free town moorings. I like spending the night there, then NYC is a short run and you can go thru in the morning while the weather is a little calmer.
After NYC I like to anchor in Haverstraw Bay which is on the east side above Tarrytown. But NOT on a weekend.
Roundout Creek is a great overnight stay. The town docks are right intown so it's an easy walk to restaurants and the small museum.
After that I usually anchor behind Houtailing (sp?) Island on the E side just below New Baltimore. A little noisy with the commuter trains but after a couple of hours you get used to it. LOL

Hope this helps Have a great trip.
 
Lots of opinions, no right or wrong answers. If leaving Narragannset for NYC, I personally would skip Block. It's a little out of the way anyway and not my favorite place, but like I said, some people love it there. You'll also bypass the Race, which can get hairy at times. I've never been to Stonington by boat but it's a pretty harbor. I hear the yacht club is great and they welcome transients. I happen to love Noank and the Noank Shipyard marina which is the first you will see entering Mystic river from F.I. Sound. Great seafood at the marina and next door at Abbotts. There are so many great stops in that part of CT, hard to go wrong. Essex is worth the trip if you've never been. Griswold Inn is a unique and amazing place to eat/drink. Unlike Prh above, I'd advise against the Thimbles as much as I love it there. Navigating can be tricky with lots of underwater rocks, and anchoring can be hit or miss depending on the wind and waves that day. Better left to locals or someone who has been there before. Clinton has a great marina but no anchoring really. Branford is also great for either. Once west of Branford you are better off on the south side of the sound. Mattituck is the first possibility, then Port Jeff. PJ is almost a must, especially for the large mooring field and anchorage just west of the harbor entrance. Follow the shore. The town of PJ is OK, little touristy, but good if you want restaurants. You can get a mooring from the yacht club with launch service. There is also a pumpout boat that will service you at anchor or a mooring. From there you can reach NY or any of the other harbors on Long Island as you head west. Time Hell's Gate so you arrive there at high tide and you will ride the current into and out of it with no standing waves or strong currents to deal with. Never anchored behind the statue, but lots of boat traffic in the area so not sure how calm/rough it may be. Liberty Landing is expensive but very nice facilities and restaurant. The plus is you can catch a ferry from there into lower Manhattan if that interests you. Some great places to eat/drink if you know where to go. Going up the Hudson, try to time the tides if you can. I like Croton Point as an anchorage. Protected and good holding. I prefer the north side inside the "elbow" but depends on wind direction.

Lots to think about. You could spend the whole summer in Long Island Sound so hard to pick 1 or 2 favorites. If you begin to narrow down your itinerary I'm happy to provide more details on any particular place. Could even meet you along the way. For instance PJ is only about an hour ride due south across the sound for me. Hope that helps you get started. Enjoy the trip!
 
JLeonard...forget about that BI anchorage. My sailboat up there draws 7' 6" so that was never an option.

Whatever ya do, I assume you have the bible...?

Eldridge for all things tide and most importantly currents.
 
This is my first extended trip out of home waters. Here is what I am trying to figure out. If I travel 40-50 miles per day how many days will I need to go from my homeport in Swansea to New Baltimore NY? Then I can figure out how much time I have in between for any visiting. I like small harbor towns and dislike cities. I am allowing 10 days max including weather delays to go from here to there. Prefer anchoring or mooring. By this time next year I should good at planning right now I am learning and you are my teachers. Thanks
 
Matt,


My preference is to plan about six hours of steaming a day and four or five days a week. We cruise at seven and a bit so six hours gives us about forty miles. This is a sustainable rate for a longer cruise. One needs time to see the areas that we pass through. Pay attention to currents and use the tides to your advantage. Sit out bad weather because it is not much fun. Download OpenCPN and charts and also use Google Maps and dream your trip. You will be entertained for hours.


Like the rest of us.
 
Do the yacht clubs mentioned offer space to all or just to reciprocals?
 
This is my first extended trip out of home waters. Here is what I am trying to figure out. If I travel 40-50 miles per day how many days will I need to go from my homeport in Swansea to New Baltimore NY? Then I can figure out how much time I have in between for any visiting. I like small harbor towns and dislike cities. I am allowing 10 days max including weather delays to go from here to there. Prefer anchoring or mooring. By this time next year I should good at planning right now I am learning and you are my teachers. Thanks

10 days should be more than enough, you could probably make it in half that time. For someone who is about to take on The Loop, you should minimally be able to look at some charts and know your intended daily range and be able to estimate that. I admire your sense of adventure, but are you sure you have the skills and know-how to navigate the loop especially single-handed? Do you know the route, have the charts, have equipment for extended cruising? Have you thought about handling canal locks by yourself? It's a great dream to pursue, but is it wise to do it as you first extended cruise away from home? You could spend the summer exploring Long Island sound and even go up the Hudson to Lake Champlain and back if you wanted a taste of what long solo cruising involves before you depart for a year. I don't know anything about you or your boat or your capabilities, and I wish you luck, but I can't ignore some obvious red flags. I hope you are not planning on going with a group of other loopers because that likely won't work out for long.
 
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Do the yacht clubs mentioned offer space to all or just to reciprocals?

The yacht clubs I mentioned offer dockage or moorings to all transients. Some yacht clubs are set up for that and some are not. Some will give a discount to reciprocals. Good cruising guides for the area will tell you and you can often look them up online.
 
I have all the charts, waterway guides, tools and electronics. I do know how to read charts and use my electronics. I also spend time every day researching anything I can think of to expand my knowledge. I feel very confident doing the Loop solo. I have been through a lot of situations and some severe weather conditions on the water over my lifetime. I know water, wind, current and weather are to be respected. My asking this question was; a) looking for good anchorages spaced far enough apart. b) Making sure my plan was on target. c) I respect the knowledge of my peers. For me this trip is not so much about being with other as it is for filling a lifelong dream. I am retiring the end of April with a plan to cruise until I am no longer able. I have my wives blessing to go. She likes a weekend away but this is not her thing.
 
Sounds good Matt. Sorry if I sounded too harsh. I just figured you should be able to chart the distance to get there and divide it by the 40-50 miles you want to cover and know the required time. I think you'll have plenty of time to get there. I didin't look into it but you are probably in the neighborhood of 200-250 miles? I'll get back to you with more recommendations on good places to stop now that I know what you prefer. Is it safe to assume you don't mind a mix of marinas and achoareges or do you strictly want to anchor? Also what is your cruising speed? If you have 10 days, there's no need to cover 50 miles a day unlesss you are running late. Maybe a less agressive schedule with more time to enjoy the trip would be a better plan.
 
I cruise about 7 mph can push it a bit to 8.5 but at 7 I burn under 2 gph. I can mix anchorages and marinas and will play it by ear. I will not be in a hurry but I do love being at the helm underway. I would like to be anchored by mid afternoon so I have time to take my dog for a run.
 
What is your cruising travel speed ? That will mathematically give you the answer about duration. We are an 8kt trawler so 6 hrs per day will average 45 nm per (not including the fun with tides). 6 Hrs per day is a lot in choppy weather. Anchoring as much as you can will speed your time up. In a slow moving boat going "offcourse" will consume a lot of time. For example. From the jetty in Old Saybrook in Long Island sound it takes us one hour to get to the port of Essex. So figure 3 hrs out of your way including docking to have a beer at the Griswold Inn ?
 
TJM, If I do go to Essex I would do an overnight just to visit the Griswold Inn it sound like a fun place. As far as choppy weather goes, I have boated in Mount Hope and Narragansett Bay all my life. The sea breeze comes in about noon and blows 15 to 20 SW. The real slop is on a falling tide with all the weekend boat traffic. Block Island Sound is the same **** just on steroids. This is what I am used to boating in.
 
I cruise about 7 mph can push it a bit to 8.5 but at 7 I burn under 2 gph. I can mix anchorages and marinas and will play it by ear. I will not be in a hurry but I do love being at the helm underway. I would like to be anchored by mid afternoon so I have time to take my dog for a run.

Thanks Matt. That implies 6-7 hours of cruising each day. I think you could do some shorter days and still have plenty of time to get where you need to. Being that you want to get off the boat with the dog, marina in some places will be much more efficient than anchoring since you are only staying one night. Given you have to anchor then dinghy to/from the land at least once and maybe more, a marina is much more efficient time-wise.

Looks like your first night would be Pt Judith or Stonington depending on how far you get. I've never been to either but both are great from what I hear. Stonington has a nice yacht club, look them up online. I think you can anchor in Pt Judith, not sure about Stonington, but they do have moorings. You could also anchor in Fisher Island Sound or as I said earlier Noank is a great little harbor and quaint town. Noank Shipyard next door to Abbotts lobster is a favorite stop of mine. From there you can cross the sound to Mattituck. It's a great couple mile winding cruise in the channel to get to the head of the harbor. There is an anchorage there and very short dinghy ride to the town dock. Quiet and well-protected, quaint little down a short walk down "Love Lane" where you'll find good small shops for food/wine/cheese etc. Next stop should be Port Jefferson. Popular large anchoarge just west of the channel entrance and well marked. Good holding and generally lots of room. Pumpout boat avaialble by VHF. Big beach/bluff area to dinghy to. From there you probably want to stop at any of the harbors between there and NYC, like Lloyds, Huntington, Oyster Bay, Glen Cove. I've only been to Lloyds Neck, west of East Beach inside the peninsula, where there is a large private mooring field and some anchoring. Should be mostly empty during the week, busy on weekends. From there you can make it to the Statue of Liberty but be sure to time Hell's Gate. Not sure where you can dinghy from there with the dog, never anchored there. Liberty Landing is best bet for a marina but expensive. Lots of commercial traffic in the NY harbor so be cautious and alert. From there I think you could reach Croton Point. Good large anchorage there. Going north on the Hudson there are many small family-run marinas that are very reasonable. We stayed at one in Kingston which was very nice and quiet and away from the Hudson a little bit. From there you can reach New Baltimore. hope that help, let me know if you have any questions.
 
TJM, If I do go to Essex I would do an overnight just to visit the Griswold Inn it sound like a fun place. As far as choppy weather goes, I have boated in Mount Hope and Narragansett Bay all my life. The sea breeze comes in about noon and blows 15 to 20 SW. The real slop is on a falling tide with all the weekend boat traffic. Block Island Sound is the same **** just on steroids. This is what I am used to boating in.

Griswold Inn is worth a stop and you can likely spare the time. Nearby Hamburg Cove is a popular spot for anchoring/mooring. I've never been but supposedly very nice but crowded on weekends.
 
Right now I am thinking of Anchoring at Fishers Island which will be a long first day. Then I think Essex for a Griswold visit. After that Port Jefferson then to Port Washington. Anchoring at the Statue of Liberty is not a must do. I am using it as my official starting point of the Loop.
 

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