Where to go in Southern New England?

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jviss

jviss

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Feb 5, 2004
7,090
Tartan 3800 20 Westport, MA
Well, it's our eight year cruising, down to just we two, kids aren't available or interested enough to accompany us this year. We've cruised from our home port of Westport, MA East to Cuttyhunk, Tarpaulin Cove, Vineyard Haven, Edgartown, Nantucket; West to Block Island, Montauk, Stonnington, Mystic, Old Lyme, Milford, Larchmont, and back to Port Jefferson and Mattituck. Up Buzzards Bay once or twice to Padanaram. So, where to go this year? We have about 1o days. Looking for beautiful places, places where we can anchor (don't care for slips or moorings), on-shore facilities including bars and restaurants, fresh water and pump-out availability. Thanks! p.s. provisioning tomorrow, leaving the 4th (probably).
 
CalebD

CalebD

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Jun 27, 2006
1,479
Tartan 27' 1967 Nyack, NY
What about Shelter Island, Sag Harbor, Greenport

the Peconic Bays, the North Fork vineyards etc? Northport Harbor or Oyster Bay? If you are really out of ideas consider cruising the Hudson although there are not many anchorages. It is quite different then the Sound in landscapes. Have fun and let us know where you end up going.
 
jviss

jviss

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Feb 5, 2004
7,090
Tartan 3800 20 Westport, MA
range

Thanks, but the Hudson is really out of range for a 10 day trip from Westport, MA. Can you give me some specifics on the places you mentioned, like, ability to anchor, and on-shore stuff?
 
Ctskip

Ctskip

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Sep 21, 2005
732
other 12 wet water
Have you been to the Thimble Islands

in Stoney Creek, Branford,Ct? Great food and drinks. Great places to drop the hook and wonderful beaches. Lennies Indian Head Inn is super for grub/grog. Guilford is really historic as is the Connecticut River at Saybrook. Great coves 1/4 mile up river on the left. Just watch the tides, which I'm sure you are aware of. Wish it were me going. Share some pictures. Keep it up, Ctskip
 
R

Rob19574

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Feb 4, 2005
524
Catalina C-30 Mattituck, NY
Eastern LI

Yes - I second Eastern LI. There is also Three Mile Harbor in East Hampton that is a great place to anchor and explore. I would do Greenport harbor, Shelter Island and Three Mile Harbor. - Rob
 
tweitz

tweitz

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Oct 30, 2005
290
Beneteau 323 East Hampton, New York
Thimbles and Easter LI

I just did the trip from Three Mile Harbor in East Hampton to the Thimbles, then Saybrook and back. Great cruising grounds. I would add Shelter Island and also consider going up the Connecticut River to Essex.
 
jviss

jviss

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Feb 5, 2004
7,090
Tartan 3800 20 Westport, MA
Thimbles

where would the "great food and drinks" be, on the mainland? I wasn't aware of any commercial establishments on the Thimbles.
 
tweitz

tweitz

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Oct 30, 2005
290
Beneteau 323 East Hampton, New York
Thimbles

We stayed at a friend's dock in the Thimbles and took his motorboat to Branford for dinner, so I can't comment on the available facilities ashore.
 
CalebD

CalebD

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Jun 27, 2006
1,479
Tartan 27' 1967 Nyack, NY
Ctskip lived in CT for many years

I have lived on LI for most of my time. Checking my chart book, Sag Harbor has a designated anchorage area and the main dock is right in town w/restaurants and of course crowds in the summer. 3 Mile Harbor has an anchorage but is a bit out of 'town' although there are restaurants and marinas along the eastern shore. Nice swimming/fishing in Gardener's Bay. I am pretty sure that Greenport is a slip-only port (no anchoring) but the town is right there. Shelter Island is a bit sleepier (out of the way for most) but I think you might have to take a guest mooring. Everywhere on the 'East End' of LI will be relatively crowded with people as this is the season. Further west it will still be summer but without the crowds. Further west is Mt. Sinai harbor then Port Jefferson where you can anchor but there are ferries to CT. Huntington Bay is next and has anchorages and I gather that Northport is a fairly boater friendly place as is Huntington. The little harbors off Huntington Bay are packed pretty full of moored boats so anchoring might be difficult. Oyster Bay has an anchorage and restaurants within walking distance of the dock. Hempstead Harbor (where I learned to sail) does not have much to recommend it in terms of restaurants on/near the water, much less anchoring. Coastal Pilot 2 has all of the 'official' anchorage areas spelled out in it. Of course there is going to be no one to stop you from dropping an anchor outside a designated anchorage area. Some harbor masters are more 'vigilant' then others.
 
BarryL

BarryL

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May 21, 2004
1,119
Jeanneau Sun Odyssey 409 Mt. Sinai, NY
Peconic Bay

Hello, As others have mentioned, the peconic bay would be a good choice. If you have been to Montauk you were just about there. Just head further west, don't hit Gardner's Island :) and you are there. On the north side is Greenport, on the south is Sag Harbor, with Shelter Island in the middle. I was at Greenport last summer. You can't anchor, but the town has cheap slips. I stayed at the Townsend Marina and it was great. Greenport is a real town with restaurants, shopping (including Preston's, a great chandlery), etc. You can easily get to wineries and beaches from Greenport. Sag Harbor is also nice but will be more crowded. Note that there is a bridge that will prevent you from going to some marina's. West of Sag Harbor is a nice wildlife sanctuary (Morton's) with birds you can feed. Here is all the information you need: http://www.boatli.org/cruise.htm Good luck, Barry
 
seadaddler

seadaddler

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Dec 19, 2006
5,832
Hunter 36 Punta Gorda
ospreysguide.com

Great info on the east end Long Island,anchoring out side sag harbor and shelter island,plenty of places to explore with a dinghy. I keep my boat in Greenport and still have lots of places to anchor out in a cove around shelter Island and greenport and sag harbor. Plenty info Ospreysguide.com This weekend will be busy because of the holiday,I am heading out late thursday maybe early friday all around Shelter Island, sag harbor ,greenport. My wife is sort of under the weather so might just do day sailing so if I can help with info just jump in here I have wifi at the marina.
 
M

Mike

Don't forget Derring Harbor

Derring Harbor on Shelter Island is a stone's throw from Greenport. It is located in a quaint little village without all of the hustle of Greenport. You could dink it over to Greenport, or take a hike to the ferry. Have you checked the weather for this weekend? Looking sort crabby. If the weather holds, I'm thinking of heading to Sag Harbor. Mike
 
B

bffatcat

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Jun 8, 2004
853
Pearson 26W Marblehead
Why not try something different

youve got 10 days why not try Cape Ann still considered southern NE maybe Casco Bay not southern NE but certainly something different, Seems like youve already been just about everywhere around buzzards bay cape cod and the islands
 
Ctskip

Ctskip

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Sep 21, 2005
732
other 12 wet water
On the Thimbles there is absolutely nothing

but a few homes, if my memory serves me correctly. Along the shoreline, I believe it's Stony Creek and theres a couple of places right on the shore line. Near the town beach and there's a marina next door. Wonderful quaint bars up and down there. I haven't been back there in some 5 years. Keep it up, Ctskip
 
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