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Old 02-09-2021, 10:02 AM   #61
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We went into cuttyhunk a couple years ago and are itching to go back. You pretty much have to get a mooring ball, or else anchor outside. They're first come-first serve and we barely got one when we went early season. The island is worth a day or two, some great hiking but not much else. Bring your bass fishing gear, of course.
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Old 02-09-2021, 10:06 AM   #62
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Thanks Gabe, we will likely try to go mid-week. The saltwater fly rod is a frequent companion.
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Old 02-09-2021, 10:19 AM   #63
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I've also heard Cuttyhunk is good and looks to be even better protected.
Hadleys inside is well protected from all winds and seas. Hadleys outside of Bull Island is well protected from southerly seas and moderately protected from the typical SW breeze that usually dies in the evening. Outside is not protected from north wind but there is only a short 1 mile fetch from the north so pretty good in northerly except in a true storm.

Cuttyhunk inside the pond is like Hadleys inside. Cuttyhunk outside is protected from all directions EXCEPT North. Pretty much wide open to the north
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Old 02-09-2021, 11:07 AM   #64
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Thank you.
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Old 02-09-2021, 11:44 AM   #65
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Thank you.
I should have added that in a true northerly, Tarpaulin Cove on the Vineyard side of Naushon is a classic harbor of refuge and beautiful too. Only great in a north storm but decent for typical summer weather where the southwesterly usually dies at night. In the summer, get as close to the single antique residential building as is practical to minimize the effect of the SW swell. It's the old post office. Lot's of tales of schooners fighting for their lives trying to make it to Tarpaulin in a nor'easter.

Also, in mild weather from the SW, Quick's Hole has a lovely small anchorage on the western side. Utterly unprotected from the north or east but a beautiful spot. A bit of a late night wake issue as the big fishing trawlers from New Bedford use it to reach the George's Bank.
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Old 02-09-2021, 01:29 PM   #66
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........ along with Fishers.
I've seen you mention this a couple of times, so I have to mention it. There are only two harbors on Fishers island.

West Harbor: Has a few moorings and a restaurant, and an ice cream shop.

East Harbor: Tiny anchorage. No means to go ashore.

I personally wouldn't bother with either harbors on Fisher's island. Mystic, CT and Watch Hill are significantly better. If I were doing a stop-over I'd take a mooring in West Harbor. There is more to do on Bank Street in New London, even if just a stopover. The New London Moorings are admittedly somewhat urban and there is train and ferry noise. However, there are a ton of restaurants and bars if you want to leave the boat.

If you're going to go through Fishers Island Sound, I would focus on New London, Mystic or Watch Hill. Plenty of room in the Watch Hill anchorage.

You can also anchor at Rams Island, but you can't go ashore there either.
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Old 02-09-2021, 01:49 PM   #67
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I've seen you mention this a couple of times, so I have to mention it. There are only two harbors on Fishers island.

West Harbor: Has a few moorings and a restaurant, and an ice cream shop.

East Harbor: Tiny anchorage. No means to go ashore.

I personally wouldn't bother with either harbors on Fisher's island. Mystic, CT and Watch Hill are significantly better. If I were doing a stop-over I'd take a mooring in West Harbor. There is more to do on Bank Street in New London, even if just a stopover. The New London Moorings are admittedly somewhat urban and there is train and ferry noise. However, there are a ton of restaurants and bars if you want to leave the boat.

If you're going to go through Fishers Island Sound, I would focus on New London, Mystic or Watch Hill. Plenty of room in the Watch Hill anchorage.

You can also anchor at Rams Island, but you can't go ashore there either.
No question that New London, Mystic and Stonington have way more services than Fisher's Island. But that's the point of a stop over on Fisher's. I've only anchored a few times in the West Harbor and it is a delightful spot to hang on the hook. Fisher's Island is good for a lovely walk but not for the bar scene or choice of restaurants. Anchor, go for a walk, come back to your boat and cook dinner and have a peaceful evening.
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Old 02-09-2021, 02:16 PM   #68
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Thanks for the info. With the dog we are limited to going out to eat and shop which is fine. Pre-COVID I traveled so much for work the last thing I wanted to do was go out so we prefer to find more isolated or quiet areas and then just take walks or meander.

That said I like new experiences and appreciate the feedback on some areas and offer other options.

That said I am all for a meet up somewhere this summer.
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Old 02-10-2021, 02:25 PM   #69
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Watch Hill limits dogs on the beach from 7am - 7pm from Memorial Day - Labor Day. However, you can take them to the dinghy dock and walk the grassy park along the seawall. You can't land in Rams' Island, East Harbor.
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Old 02-10-2021, 02:44 PM   #70
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Once you enter Long Island Sound, you could spend the summer and not see all the best marinas and anchorages. On the CT side, Essex is a great little town, Griswold Inn is a must. I like Noank better than Mystic. Quieter, great marina and restaurants. Branford is great as is Milford. Clinton has a great marina with lots of services, restaurant, etc. On the NY side, Mattituck is nice, but limited room for anchoring, then not much till PJ which I like for anchoring or a mooring at the yacht club if you want to go into town. Town can be very busy and crowded. Huntington and Lloyds harbors are also good. If you haven't been in or around Shelter Island, lots of great spots there as well. I can provide more info if you have any specific questions.
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Old 02-10-2021, 11:25 PM   #71
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I'm sitting here in South Dakota with frost on the inside of the triple pane windows, wearing my Griswold Inn sweatshirt. My initials are carved into the bathroom woodwork at the Gris, during our high school senior reception dinner in 1980. (You'll see, the carved memorials are a thing at the Gris.) My Chester home boy affection aside though, when we bought our current boat in Newport four years ago and motored it from Newport to Albany, we spent one too-short day and night at Essex Island Marina. It was kind of selfish of me, I just wanted to take that detour up the River for old times sake. To my surprise though, when the three week trip was all over, my Wisconsin wife and our good friends from Arizona who helped us run the boat all said the evening and dinner at the Gris was one of the high points of the whole trip. Good memories.
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Old 02-11-2021, 06:53 AM   #72
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Thanks for sharing! My yacht club plans a club trip to Essex Island marina every summer. The Griswold is a truly unique place that can't be missed if anyone is in the area. For those of you that will never get there, you can look here and be sad: https://griswoldinn.com/

The only other place I can think of that is equally interesting is the Fraunces tavern in NYC in a very historic area at the southern tip of Manhattan and other cool places nearby like the Dead Rabbit.
https://www.frauncestavern.com/about
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Old 02-11-2021, 02:43 PM   #73
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Well if we end up buying the boat I'm looking at next week, wife is still encouraging me, we hope to move the boat from St Petersburg, FL. starting in March. We will first cruise around the southern tip of Florida, then start north. WE hope to get to the Chesapeake by late May or early June. Then have to fly home for my Mother-in-laws 103 birthday and my son and wife are having our first grandchild, due in last June. Then will fly back and spend the summer cruising the Chesapeake, before laying up for the winter, somewhere in the Chesapeake area. Hoping in 2022 do start on the loop, hoping Canada is open by then.

I will probably be asking for your favorite cruising spots, from those of you that have cruised the Chesapeake or live in the area. Thanks in advance
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Old 02-11-2021, 02:57 PM   #74
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Lots of hoping. Somebody once told me, "hope is not a plan!" Anwya, I "hope" it all works out for you!
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Old 02-21-2021, 10:13 PM   #75
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Hi folks, been lurking on the forum since last summer when I purchased a Cutwater 26 with a trailer. I'll be following this thread, I'm eager to participate in a northeast cruise or rendezvous this summer. Cheers
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Old 02-22-2021, 11:45 AM   #76
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Hi folks, been lurking on the forum since last summer when I purchased a Cutwater 26 with a trailer. I'll be following this thread, I'm eager to participate in a northeast cruise or rendezvous this summer. Cheers

You are right down the road from us here in Hampton Beach. Prior to buying our current boat, we did years of trailerboat cruising in the north east and had a blast. Have you towed your Cutwater to 1000 Islands yet? We towed our last boat there a couple of times and had wonderful times. Another great trip is to the free launch ramp on the Penobscot River in Hampden ME, less than 3 hours up 95 and you are in one of the nicest cruising areas in the world (mid-coast Maine).
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Old 02-24-2021, 11:24 AM   #77
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Have you towed your Cutwater to 1000 Islands yet?
Not yet but I've heard it's beautiful there. I'll add that destination to my list.
I am familiar with mid-coast Maine and a Penobscot bay trip will happen this summer for sure.

The other suggestions around Buzzards Bay to LI sound great also.

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Ok that's two votes for "late July"
I'm on board for late July also
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