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I have an opportunity to rent a house with a sailboat on the eastern CT shore. I was wondering what the sailing is like in the summer on the eastern LIS. Anyone with any experience in this area would be appreciated.

Thanks
 

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Do you mean the Eastern end of CT? If so, then it simply doesn't get any better than that. I believe that the Eastern end of CT one of the top areas of the US for cruising sailing adventures. Much better than the Western end of CT. We lived and sailed out of Mystic CT for 18yrs. You can daysail all the way up to Cape Cod, Martha's Vineyard, Nantucket, and Buzzards Bay. Newport, Block Island, the Eastern Forks of Long Island (Montauk, Hamptons, Sag Harbor, Shelter Island, etc) and more are only an afternoon's sail away. Fisher Island Sound is protected water in almost all weather, so if it is not great weather for adventuring farther, you can still sail out to Fisher Island, Stonington, Essex, New London, and other places along the coast. Lots and lots of small towns to anchor off and explore by foot, as well as wilderness areas to do the same. If you feel like sailing West, there is this town called "New York" that I've heard has a few things to see in it.

If you have a house and sailboat for the summer anywhere near the Mystic area of CT, it will be the best summer ever. I had 18 of those summers and still miss them. We left and have explored the Chesapeake many times, as well as the Bahamas and the entire Caribbean Sea. There is nothing like summer sailing in New England.

As far as the sailing itself goes, the predominant winds are SW, and they get light during the summer there. When they are light, you can count on a seabreeze picking up in the late afternoon into early evening. This is a magical time for a couple hours sail. The water stays cooler until late summer, so the air on the water is also cooler. Don't be fooled by high inland temps - it will be much cooler on the water. You will need a sweatshirt at night. Humidity is high, so the afternoons with light winds can feel warm, but that doesn't last long. When a cold front comes through, the winds switch to the North which is offshore there, the humidity goes away, and sailing along the CT coast doesn't get any better - good winds and flat seas with crystal blue skies while you beam reach along the coast, then beam reach back home.

The season is short, though. But it will be the best there is.

Do yourself a favor and pick up this book: The Coast of Summer: Sailing New England Waters from Shelter Island to Cape Cod by Anthony Bailey (1995-08-01): Amazon.com: Books

Mark
 

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What Mark wrote... I had a mooring in Dering Harbor, Stirling Harbor and Sag Habor for 20 years and now have one in OId Lyme. Great jump off point for all sorts of lovely harbors and anchorages.... and great sailing. Much much better than Western LIS and in my opinion better than Narragansett Bay... which is more "commercial" and developed / crowded... but fabulous as well. You can do MV and Nantucket and Block.

Can't beat the East End location. Our mooring is 4 minutes from I95 ... and our apartment is 2 minutes from the highway. I can get from my home without a traffic light or hitting the brakes!
 

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Great place to sail in the summer. It’s why we usually leave the Chesapeake during the hot time here and spend time substantial timein that area. Last year we concentrated on Mystic/ Stonington/ Old Saybrooke/ Newport.

The sailing seasons so short there I don’t rate it overall the best though. Boaters pulling out for the winter by October while they are the best months on the Chesapeake. But in the summertime it’s great. Most people consider where they keep their boats the top spots. Not fair to compare to say a 3-4 week trip to the Chesapeake. You really don’t get to know the area that well in that short a period of time.

Have fun where you are going in Eastern LI. Feel free to ask on here favorite anchorage spots , local knowledge.
we love our time up there ( that’s why we keep returning year after year.😄
 

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Do you mean the Eastern end of CT? If so, then it simply doesn't get any better than that. I believe that the Eastern end of CT one of the top areas of the US for cruising sailing adventures. Much better than the Western end of CT. We lived and sailed out of Mystic CT for 18yrs. You can daysail all the way up to Cape Cod, Martha's Vineyard, Nantucket, and Buzzards Bay. Newport, Block Island, the Eastern Forks of Long Island (Montauk, Hamptons, Sag Harbor, Shelter Island, etc) and more are only an afternoon's sail away. Fisher Island Sound is protected water in almost all weather, so if it is not great weather for adventuring farther, you can still sail out to Fisher Island, Stonington, Essex, New London, and other places along the coast. Lots and lots of small towns to anchor off and explore by foot, as well as wilderness areas to do the same. If you feel like sailing West, there is this town called "New York" that I've heard has a few things to see in it.

If you have a house and sailboat for the summer anywhere near the Mystic area of CT, it will be the best summer ever. I had 18 of those summers and still miss them. We left and have explored the Chesapeake many times, as well as the Bahamas and the entire Caribbean Sea. There is nothing like summer sailing in New England.

As far as the sailing itself goes, the predominant winds are SW, and they get light during the summer there. When they are light, you can count on a seabreeze picking up in the late afternoon into early evening. This is a magical time for a couple hours sail. The water stays cooler until late summer, so the air on the water is also cooler. Don't be fooled by high inland temps - it will be much cooler on the water. You will need a sweatshirt at night. Humidity is high, so the afternoons with light winds can feel warm, but that doesn't last long. When a cold front comes through, the winds switch to the North which is offshore there, the humidity goes away, and sailing along the CT coast doesn't get any better - good winds and flat seas with crystal blue skies while you beam reach along the coast, then beam reach back home.

The season is short, though. But it will be the best there is.

Do yourself a favor and pick up this book: The Coast of Summer: Sailing New England Waters from Shelter Island to Cape Cod by Anthony Bailey (1995-08-01): Amazon.com: Books

Mark
I second the suggestion for the Anthony Bailey book to get a feel for the area.
 

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We’ve been sailing out of Mystic for 51 years and agree with all of the preceding posts. The furthest west we’ve sailed from Mystic is Shelter Island, inside the “fishtail” of Long Island. Favorites in our area are Fishers Island and Watch Hill (Napatree Point) for day trips. Next is Block Island, and Long Island (Lake Montauk, 3-mile harbor). Then there is Pt Judith and on to Jamestown and Newport. Continuing East, there is Third Beach (Sakonnet River) and then Cuttyhunk, Padanarum, Menemsha, Tarpaulin Cove, Lake Tashmoo, Vineyard Haven, Hadleys Harbor, and Edgartown. If you have a week or more, Nantucket is in reach, as well as Plymouth and Provincetown via the Cape Cod Canal. If you have more than a week, there is Gloucester, Manchester-by-the-Sea, Isles of Shoals, and on to Maine. In 2 weeks you can explore York, Portland, Casco Bay and on to Boothbay, with stops at Seguin island and Damariscove.

All that said, you can spend an enjoyable summer on the water entirely within Fishers Island Sound and Little Narragansett Bay.
 

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I second, third, fourth or whatever all that is said above. And the Bailey book. I've sailed out of Branford for the past twenty plus years, and there is no shortage of day sails, over night destinations or longer trips you can take. I've gone as far west as Bridgeport (don't laugh. Captain's Cove on a summer night is every bit as much fun as Foxy's or the Soggy Dollar. Just not as pretty), and as far east as Groton. If your thing is marinas, there are tons of them. If you like anchoring out, there are lots of protected coves and other spots. Come join us!
 

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Cole and the others have summed things up pretty well. Though the places he visited have changed a lot since, Bailey's book is great for projecting the sailor's point of view - somewhat reminiscent of Hereshoff's Compleat Sailor - and for being superbly written. (He wrote at The New Yorker for 30 years.)
 

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The sailing weather and options between the West end of LIS and the East are dramatic. West LIS has limited destinations... but there are some lovely ones for sure... but the sound is narrow and much more congested with traffic... and LGA is close and makes for constant lot of airplanes overhead. Part of LIS is in NYC so that tells you a lot about traffic. As someone who lived in NYC the East End feels far away from the maddening crowds. West End not so.
 

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Major vibe difference from Western to Eastern LIS. Grew up boating on Western with family, where there is very much a NYC vibe. Eastern more a New England vibe.
 

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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😁
 

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One thing to be aware of in the Eastern end of LIS and areas like Stonington, Newport and areas east is occasional Fog. I was anchored in Watch Hill one time and saw the most dense fog I had ever seen. It becomes less prevalent the further west one sails. It usually clears eventually but, if you are not use to it it can be unnerving if you are underway. Though it is awesome to see if you are safe at anchor.
 

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One thing to be aware of in the Eastern end of LIS and areas like Stonington, Newport and areas east is occasional Fog. I was anchored in Watch Hill one time and saw the most dense fog I had ever seen. It becomes less prevalent the further west one sails. It usually clears eventually but, if you are not use to it it can be unnerving if you are underway. Though it is awesome to see if you are safe at anchor.
Interesting observation... YES there seems to more fog east of Montauk. I have seen some dense fog in Block Island & Rhode Island Sound... West Harbor , FI, Stonnington and the waters north of the Race. While I have seen for further west it is not as dense, as often or as widespread. I suspect it is because the fog is coming off the ocean and the air is not warmed by Long Island.
 

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The East end of LIS is great. Hope its okay that I share this, but - SandrO and I sailed from the Connecticut River to Shelter Island last week on Shiva. Was a great time. Here wer are crossing Gardiners Bay.

And here is a shot from our mooring ball in Dering Harbor

sunset.jpg
 

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I can say from experience that fog in Fisher Island Sound can be signficant. Once got stuck for days in Stonington (before I had Loran or GPS) in dense fog. Another issue of the east end is currents. Not a major issue for powerboats, but sailboats hoping to make a decent distance have to time their transit to avoid going against the current. Fun when you are with it, but frustrating when trying to get to a destination and it's against you.

To put in a pitch for the western Sound, fog and currents are not an issue. And unlike the eastern Sound, there are lots of harbors, anchoring spots, and gunkholes on both sides of the Sound. After Pt. Jeff, there's really only Mattituck for sailboats to duck into along the LI shore. I'm glad I have both ends of the Sound to enjoy.
 

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and you don't have to be particularly far east to feel those tides. We were out for a day sail on Sunday for Father's Day, and leaving from Branford (just east of New Haven, about smack in the middle of the CT shoreline) with a south wind of less than 10 knots, we were doing about 5.5 knots SOG heading almost directly east. On the way back with the tide heading out, same wind, we never made much more than 3.5 knots heading west.
 

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I don't think anyone mentioned New Bedford, MA. It's not the most beautiful city, but is historic, for its whaling and fishing history. The whaling museum is great.
If you remember the beginning of the book Moby Dick, Ishmael visits a seamen's chapel in New Bedford, which he gives a good description of. It's still there, I went to a cousin's wedding there. Worth the time.
I spent a bunch of time on Cape Cod in my childhood and early 20s. If you go through the Cape Cod canal into Massachusetts Bay, there are many nice small town ports along the inside of the cape.
Wellfleet, just south of Provincetown, is as close as it gets to the real Cape Cod, that has not been heavily developed. It has its own bay, that's great for swimming, sailing, clam digging, fishing, etc.
And it has some of the best beaches on the outside of the cape, just a few miles away. The Cape is quite narrow there, even narrower from there to Provincetown. Provincetown is where the Pilgrims spent their first winter.
Which brings up Plymouth, on the mainland, with its historic Plymouth Plantation.
 

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Discussion Starter #19
Thanks for all the thoughtful replies.

I live in FL but have been spending the last few summers in Provincetown and sailing out of there - which I love. But each year it gets more prohibitively expensive so I have been looking for a new location that is less expensive, easier to get to, and has access to good sailing.

Seems like I may have found it with eastern CT.

I thought I had heard before that the winds on LIS in summer were not that great, but I'm not sure that's true. The limited experience I have sailing in the Northeast has me dreaming of more.
 
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