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I have sailed this area for the past 60+ years. Way back when you had to use a chart and a watch.
From that end of LIS there are lots of weekend destinations a couple hours sail away. New port and Block Island in RI. Cockles harbor, Sag harbor, Greenport, Three mile harbor on Long Island.
If you have more time you can head to the Elizabeth Islands and Cape Cod.
Lots of great sailing.
jim
 

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As a complete outsider, I have a different take.

it’s all a NY vibe until you hit Newport. Don’t really see the differentiation as all the accents are similar unti there., just less density in Eastern LI😁
As an insider at the Fishers Island Sound end, I see a differentiation, but that depends where you sample the local scene. Fishers Island itself is part of NY and there are a lot of New Yorkers in Stonington Borough, but the local scene otherwise has a different vibe than Lake Montauk, Shelter Island or Three Mile Harbor, for example.
 

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Western End of LIS is more urban as it's part of NYC. Boaters are not as upscale... few big yachts etc. There are some very upscale harbors w/ mansions/villas along the shore... Cold Springs Harbor/Oyster Bay... Centerport, Manhasset Bay... close to Manhattan. As you move East it gets mixed. Waterfront property is extremely expensive on the Sound. East end of LI has many people who have never been to NYC... there are farms and no urban feel at all. Shelter Island is isolated accessible only by ferry like MV or Nantucket... Gardiners Island has one a caretaker for the owner. Hamptons people attracted upscale restaurants and shops and even vineyards. Greenport used to be a big fishing port and build ships. Fishers Island is a bunch of very rich folks who have a semi private island accessible only by boat.

CT shore is more New Englandlike... with cities every 20 or 30 miles... Stamford, Bridgeport, New Haven, New London... There are several large sea museums and aquariums on the CT side. South Norwak, Mystic... and smaller ones on City Island and Greenport LI.

City Island is fairly unique, restaurants, shops, marine facilities connected to mainland by a causeway. It's da Bronx!

But sailing wise.. East end has it over the West end. Very clean water... better winds... and nothing like NYC.
 

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What's your favorite anchorages on Eastern CT from Duck Island Roads to Stonington? Planning on a weeks sail out of Milford to Duck Island and slowly make my way to Stonington. Typically hit up marinas on the way. This time want to be on the hook.
 

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North Cove Olde Saybrooke or Mattituck
 

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Agree on West Harbor, Fischers Island. And note North Cove in Old Saybrook is a great stop, but little room for anchoring. But there are 2 free transient moorings all the way in just off the town dock. Locals out cruising are supposed to put a streamer on their mooring to indicate it's available, but they don't seem to bother.

I heard from a friend planning a cruise that Dodsons in Stonington is not renting moorings to transients this summer. Anchorage area in the outer harbor is small. Watch Hill has plenty of room to anchor.
 

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Jim ,

Last year we anchored and moored both in the North Cove of Saybrooke. Since the dredged there seems to be ample room to anchor in spacing around the moorings, many of which were not occupied.

it’s a great place quick access to Sound so you do t have to take the hike past the bridge on the Connecticut River. Walkable got town.

We loved the East Harbor of Fishers Island as it protected from prevailing and a great jump off place for leaving the Sound or entering it.

Mattituck is lot for the faint of heart as the entrance is narrow with shallow channel. It open up to a gorgeous Federal Anchorage and a cute little town nearby

All three of these anchorages easy , not much traffic and fairly quiet.

in the “forks” there are many good spots
- all around Shelter Island quiet a few quiet places
- Montaulk, Three Mile Harbor
 
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