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Annual Long Island Sound Vacation

4K views 31 replies 15 participants last post by  jhwelch 
#1 ·
My wife and I are gearing up for our annual vacation/ visit to the Long Island Sound and beyond starting August 15.

We will be doing our usual down the Delaware , up the Jersey Coast hops visiting some of our favorite places like Cape May, Barnegat, Sandy Hook and Port Washington

This year we decided to " hang" out at at some of our favorite spots between the forks of the End of Long Island such as Greenport, Sag Harbor , Mountauk, the over to Stonington and Mystic.

Last year we visited Milford for the first time ( loved it) but want to try a few new stops on the Conneticut / Rhode Island side.

Looking for information on Watch Hill and Clinton which look like nice stops.

Dave
 
#2 · (Edited)
Welcome back!

Watch Hill is one of my favorite spots on the eastern end of LI Sound. Great beaches, small but interesting town, and anchorage with good holding in moderate depths close to both. Its a long narrow channel in from Stonington but it's well marked and maintained. Don't try it in fog. From the anchorage it's a short walk over the dunes to the beach. You can walk to town from the beach or take the dink into the cove were there is a dinghy dock to the left of the yacht club. Dining is a bit limited, but the newly rebuilt Ocean House is very classy (with prices to match).

Haven't been in to Clinton in years. A bit of a pain to get in and no anchorage spots. I usually stop at nearby Westbrook and either anchor behind Duck Island if I'm just passing east or west, or go into the Brewer's marina if we're in the mood for a real shower, want to use the swimming pool, or dinner at Bill's (a classic New England seafood shack).
 
#4 ·
Dave, if your club has reciprocity with the Manhasset Bay YC, I recommend stopping there for a nice lunch. Stopped on our way back from Newport after the A2N race. Guest moorings are red and furthest from the club. Ones to the East have painters on them. Fuel is nearby too.
Enjoy
Joel
 
#5 ·
Hey,

I have been to Clinton. We stayed at the Cedar Island Marina, which is very nice. When I was there (2012) there as very little water at low tide, but I believe the harbor has been dredged to 10' so it should be fine now. The harbor is pretty but I don't think there is really a town within walking distance.

Barry
 
#6 ·
Clinton isn't much of a sailing harbor and no anchoring options. Westbrook is a far better choice. Anchor out at duck island or shore side at brewers. Our yacht club is up the river from pilots point. We have guest slips when slip owners are away. Bills is across the street.
fyi
if you come in near closing time and want to go to "the Boom" for dinner you can usually stay on the fuel dock for the night for free.
Let me know if I can help while your in the area.
Jim
 
#8 ·
My recommendations:

Three Mile Harbor in East Hampton is a nice anchorage.

Coecles Harbor on Shelter Island is a nice spot to chill out

Mattituck on Long Island's north shore on the east end. Peaceful anchorage (harbor of refuge). Town has a park with a dingy dock and free hot showers. Provisions (supermarket) nearby too!

Mount Sinai Harbor a hidden gem three miles east of Port Jefferson. Small Mount Sinai yacht club has three blue transit moorings. Ralph's Fishing Station may have one or two also. Half the harbor is a Marine Sanctuary great for gunk holing with the dingy.
 
#9 ·
We love Mattituck. Never been to Three Mile Harbor. Is there stuff to see do near by. How about provisioning.

Been into Mt Sinai and saw Barry's c&c 115 on the mooring a year ago we thought. Are there any restaurants etched near by. We have always stopped in eclectic Port Jeff
 
#10 ·
We love Mattituck. Never been to Three Mile Harbor. Is there stuff to see do near by. How about provisioning.

Been into Mt Sinai and saw Barry's c&c 115 on the mooring a year ago we thought. Are there any restaurants etched near by. We have always stopped in eclectic Port Jeff
At Three Mile Harbor there is a small deli walk-able from the southern end of the harbor. There are also a couple of restaurants along the channel in Three Mile Harbor accessible by dingy. Then there is the town of East Hampton a high end tourist spot with lot's of little shops, cafes and restaurants. Couple of supermarkets too. Though it's a long walk from the harbor. There is a bus that operates hourly(?). Google Suffolk County Bus schedule for updated info. Also taxis could take you shopping or drop you off at one the ocean beaches for the day. I think they might also show movies on the beach one night a week.

Mount Sinai has the Mount Sinai Yacht Club which I think serves lunch dinner may need reciprocal privileges. Ralphs Fishing Station has burgers, salads, fish sandwiches etc... til 8 PM. There is an Italian Restaurant Savinos Hideaway (never ate there) nearby best to take a Taxi as it's a long walk.
 
#11 ·
Hey,

Mike has described Mt. Sinai well. If you there last year you either saw my C&C 110 or another C&C 115, both are dark blue and in the same part of the harbor. I can say that Savino's Hideaway is excellent but don't walk there. It's not THAT far but the road is very narrow and there are no sidewalks.

Regarding CT marina's, I would recommend you check out the Thimble Islands for site seeing and then head in to Branford. There are a bunch of nice marinas and some room for anchoring too.

Barry
 
#12 ·
Three mile and cockels harbor are nice for quiet and remote. Some of our favorites. Off the boat activity is primarily walking the beach.
If you want civilization sag harbor and greenport will do.
As far as the thimbles are concerned everyone I know, and I mean everyone, that has ventured there has hit a rock. The only reason I've never hit a rock there is because I won't bring my boat in there. Limited unprotected anchoring, in a cable area, from the south west. Not an area to explore w/ a keel.
There are a couple marinas in guilford and branford but no anchoring. No easy access to provisioning and last I knew low tide was a problem for sailboats.
Jim
 
#14 ·
As far as the thimbles are concerned everyone I know, and I mean everyone, that has ventured there has hit a rock. The only reason I've never hit a rock there is because I won't bring my boat in there. Limited unprotected anchoring, in a cable area, from the south west. Not an area to explore w/ a keel.
I have been in there many times and never hit a rock. I do agree that anchoring is an issue, so I normally will pick up an unused mooring. That will not work on weekends however, so I avoid them. Also only attempt it in in clear weather. I am VERY careful and stay in the main channel in and out.
 
#13 ·
Good points all thanks for the comments. We try and doing a combination of civilization and also remote seclusion. My wife likes to get off and be able to walk and enjoy a small town at least every second or third day. It doesn't have to be a marinia as we have tons of amp hours in power and a reliable dinghy

In fact I just gave up on my5 hp Tahatsu in its 5 th year and 3rd carb orator and bought a 5 hp Lehr propane outboard which we are switching out tomorrow.

3 mile sounds interesting.
 
#17 · (Edited)
The thimbals is a beautiful area, it's just very unforgiving. It's kinda like a slice of coastal Maine. A lot of the granite in Manhattan was quarried there. A coworker did $40k in damage to his boat there last summer and he keeps his boat on a mooring there.
Sachem head is very private and all private moorings. No place to go ashore other than the yacht club. If your not a member or guest of one you will not be welcome. Very exclusive old money.
No experience w/ Black rock.
We do most of our weekend cruising around Gardners bay and the Peconics.
Jim
 
#19 ·
If your wife likes to get to see a small town, you can't get anymore quintessential Connecticut than Essex. The town docks are right in the "downtown" area ("town green" is probably the more appropriate term) and there's lots to see/eat/do in a small walking area. Yes, it's a trip up the Connecticut river a little way, but it's more than worth it. This is probably my wife's favorite town in CT.

Westbrook is our home port - it has some great restaurants, but doesn't have a great town feel, if you know what I mean. Every so often they'll have weekend activities and functions on the town green, but it's no Essex. The town itself doesn't have a ton of things to walk around and look at. I've lost my wife to the scrapbooking store a few times, but other than a few sailmakers and marine upholstery places there's not much else to see and do. There's also the outlet mall, if you're into that. It's not walkable from the marinas, but it's close.

As far as restaurants go, Turtle Cafe is an awesome breakfast/lunch hole in the wall. Worth even a walk from the marinas. It gets real busy on the weekends, tho. Bliss Gourmet is very convenient, but a bit middling if you ask me. Bill's Seafood has already been talked about, but Edds Place, right next door is also very good and usually less busy. If you anchor out at Duck Island, both Bill's and Edd's are accessible by dink; the former being accessed by the Patchogue River, the latter accessed by the Menunketesuck River.

Hope this helps
 
#20 ·
Hey,

I didn't realize the Thimbles had such a bad reputation. I've sailed / motored through there a few times and never had a problem. It is well charted, and as long as you familiarize yourself with the chart you should not have any problems. It's very pretty, and even if you don't plan on exploring the area, you should at least be on that side of the Long Island Sound as you head east or west so you can see the islands.

Great information here:
The Thimble Islands, CT

Regarding Black Rock, are you referring to Black Rock Harbor, just west of Bridgeport? If so, there are a number of marina's there, including Captains' Cove, which I have visited a number of times. That is really a party marina, great if that's what you want, not so great if it isn't. Black Rock is a good stopping point if you are trying to get from point A to point B, otherwise it doesn't have much going for it.

Barry
 
#21 ·
Thanks for the tips. We have been to Essex a few times..nice town...eaten in the oldest American tavern there . Great anchorage north of there also. Conneticut River is one of our hurricane hole places if one comes up the coast while we are traveling up there.

We are planning this trip to do Gardeners area, looks like Montauk, 3 mile harbor and Greenport. Also Mattituck on the way out.
We stopped for the first time last year in Milford and stayed a couple of days. Good restaurants...not a bad place....busier than we thought it would be with quite a sailing fleet.

Dave
 
#22 ·
Joining the thread a bit late because we were out sailing Long Island Sound. Our home port is Three Mile harbor, and we spend lots of time covering the area around Gardiner's Bay. Some comments: Three Mile Harbor is well protected, lots of anchoring room, and a very pretty area. The best restaurants close to the water are Bay Kitchen Bar. located in Harbor Marina, East Hampton Point, which is in East Hampton Point marina, and Harbor Bistro. The bay beaches are easily accessible by dinghy. A cab or bus ride will take you into town in East Hampton, with lots of restaurants, points of interest and just a beautiful town. Provisions are a bit far from the water, depending on where you land. Damark's deli is short walk from the southern end of Three Mile Harbor, and there is a deli at the north end as well, at Three Mile Harbor Road and Washington Ave.
Coecles Harbor is absolutely beautiful and serene, but not much in facilities. An exceptionally pretty and well protected spot. Be careful for shoaling I the channel going in.
Greenport tends to be busy and a bit powerboat oriented for my taste, but a nice town with lots of facilities.
Sag Harbor is to my mind an ideal sailing port, a beautiful village with everything you could want an easy walk from the water. The only trick there is that it is a very busy place.
On our trip this week we stayed at a guest mooring at Larchmont Yacht Club, beautiful if you are a member or have reciprocal privileges, though the guest moorings are pretty far out in the sound. We spent a night in Branford at Bruce & Johnson's marina. It was very well protected, very friendly and helpful staff, decent and reasonably priced restaurant. We did not venture out to see what was around.
I would be happy to answer any questions that I can help with. Enjoy your cruise.
 
#24 ·
Dave, Will be in the east end bays mid to late August, leaving boat at North Sea Harbor (about 7 miles west of Sag Harbor) in between.
Would be good to make a meet.
Happy to invite you into North Sea Harbor if I'm around, wonderful quiet secluded, also very narrow approach/inlet, shallow harbor requiring some local knowledge.
But worth it once in as about half of shore line is wildlife preserve.
Hugo
 
#25 ·
If you were to go a little further east, Narragansett Bay has great appeal --generally cooler and breezier than the Sound; many pleasantly funky, walkable, historic communities; secluded anchorages; and, of course, Newport, RI. I you go I'd make the first stop at Dutch Harbor on Conanicut Island; there are moorings and at the north end of the harbor good holding ground; easy provisioning and an easy walk to Jamestown. Jamestown and Conanicut Island - RI - An Introduction for Visitors.
 
#26 ·
Watch Hill/Sandy Point channel was dredged this year, more forgiving at the start, then it opens up wide until just before the mouth of the Pawcatuck River. The eel grass in "The Kitchen" (local name for the anchorage outside the Watch Hill Yacht Club/Harbor) is notorious for fooling you into thinking you have a good hold. It's not that bad, just back down longer and harder than you think you have too as the grass will hold you pretty good until it doesn't.

The WH Yacht Club might rent you a mooring, they might not, depending on who answers and if they want proof of reciprocal yacht club membership. Honestly, Stonington is a much better place. You can dinghy over to Sandy Point for a private beach or even over to Watch Hll or Napatree Point for the day. Lots of exploring with a dinghy or even kayaks.

Spend a night at the Mystic Seaport, you will have the run of the place after it closes, it's very cool. Don't skip Noank, tiny little sailing town with a couple of restaurants, etc. If the wind is not from the North, Anchor behind Ram Island in Noank. Of course, if my mooring is not in use, you are welcome to it, PM me if you stay in the area.
 
#27 ·
Watch Hill is a wonderful spot and well worth the long channel. I can't agree that Stonington is a much better place at all...and I like Stonington. I have been anchored there (Watch Hill) in a few blows, nothing serious, and have never dragged. I tend to head a bit farther down the backside of Napatree Point and not right outside the yacht club's little harbor there. I usually drop the hook in about 10' or less at MLW and have not anchored there in grass.

The Eastern Harbor on Fisher's island is a good spot to stop and drop the hook for lunch and a swim then continue on to Stonington, Mystic, Noank, or Watch Hill.

The anchorage right near the entrance to Coecles Harbor is also a beautiful spot to stop for a bit and then continue on to Greenport, or spend the night. We carry kayaks and paddled over the beach there which had excellent shelling.

I am not going this year but usually head out to eastern LIS and Block the second half of August as well. Best time to go IMO. Well maybe just after Labor Day is even a bit better if, like me, you have no kids in school.

Thimbles are beautiful and rocky. Have never hit anything there, but have always been very careful. Only spent the night one time. It was an easy place to stop when bringing the boat home to Stamford. The local yacht club keeps moorings there that members use mostly on weekend days so we felt pretty safe in grabbing one on a weeknight in late August. You can't really get off the boat there so I only recommend it for an eat, sleep and then get on your way kind of stop.
 
#28 ·
Hugo I will take you up on the invite.

I was thinking about Watch Hill. Channel looks really long though but must be a pretty anchorage. We love Stonnngton but may skip it for that

Also last year we anchored in East Harbor of Fishers and watched the golfers. It was our jump off for Newport and Block. It was quiet and a very beautiful anchorage.

Like the Cocles idea, we will definitely go to Greenport and somewhere on the eastern fork. Like the 3 mile harbor idea also.

We are members of Mystic seaport so we will spend two nights tied up there.
 
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