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LOTS of choices. Instead of heading to the Vineyard from Cape May, consider heading towards Montauk Point (its closer) and your first stop can be Block Island. From there you east to Cuttyhunk and the Vineyard, north to Newport and Narragansett Bay or west to Long Island Sound.
 

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One suggestion when heading west towards Long Island Sound after exploring points east, take the Watch Hill Passage vs the Race or Plum Gut and stop at Stonington. Shorter hop and currents are less in case you don't time them just right. And Stonington is a great town to explore. You can anchor in the outer harbor or get a mooring at Dodson's.
 

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Watch Hill is another gem, another place a lot of people passing thru seem to give a miss.
I agree 100%. But I didn't mention it because its not really a good place to just hop in and out of like Stonington is.

I have literally spent dozens of nights anchored at Watch Hill over the last 30 years. Easily one of my top three destinations on the southern New England coast. Large anchorage with 6-10 foot depths, short dinghy ride in to one of the nicest beaches anywhere, and a short dinghy ride or walk over the dunes to a classic summer beach town with a 100+ year old carousel. What more could you ask for?
 

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Our loose itinerary this year is at 21 days
Reedy Island,
Cape May,
Barnegat,
Atlantic Highlands, love the ride up the East river
Port Washington - new for us
Milford- new for us
Mystic or Stonington- 2 days
Newport- 2 days
Block- 2 days
Montaulk
Northport,
Atlantic Highlands or Liberty Marina in Jersey City
Atlantic City
Cape May
Home
+ 2 weather days
A couple of comments on Port Washington and Milford which you indicate are new for you. Would have to confirm for this season, but Port Washington has been offering free mooring for transients. Check with the harbormaster. The water taxi will take you to the waterfront park where its a short walk to Louie's for upscale seafood or up the hill to Main Street for lots of other choices. In Milford I would suggest Milford Landing which is the last facility on the left up the river. It's run by the town and 100% transient. It's right in town with lots of eating choices. Wife and I love the Stonebridge Restaurant which has a fantastic earlybird special - two complete meals for under $30.
 

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On your way out LI Sound, if you are along the New York side, around 40.89 N 73.65 W you'll pass what looks like an estate but is Webb Institute of Naval Architecture. Please wave at my alma mater. Don't stop - you'll be sucked in and stuck there for four years.
Ah a Webbie! I was on the faculty at Kings Point for 28 years and taught Marine Engineering as an adjunct at Webb in the 80s. I live in Glen Cove about a mile from the Webb campus.
 

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Cool! After my time. You must have been after Prof's Holm and Rowen.

I sailed to Homecoming a few years ago and anchored off the beach.
The course I taught was one of Al Rowen's at the time. He was overloaded that term. One of my good friends is still there on the faculty - Ed Wiggins. He was at Kings Point with me and left to become Dean at Webb.
 

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No sorry ;) we went through much earlier...started at the Battery right at 2:15...we were under mainsail and engine until we passed through Hell Gate then had an amazing sail to Huntington Harbor. I almost thought to keep going since the weather was so perfect but choose Huntington instead ; )
Who says there's never any wind on Long Island Sound in the summer!!
 

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Yes, Block Island is a special place. Been there many times over the last 30 years and hope to go back many more. Two of my favorite things to do there:

1. Take the dinghy into "Zodiac Beach" and walk over the dunes to Crescent Beach for some great swimming.

2. Lunch on the porch of the Harborside Inn watching the ferries come and go and the crowds walking up and down Water Street.
 

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We left BI Sunday and got our asses kicked by the sound on our way west. It all started fine as we were riding the current and enjoyed a great ride until the winds kicked up to the high 20s right on the nose as we slowed to a pitiful 2-3 knots. I should have fallen off and headed for a place along the Connecticut shore but was determined to make Port Jefferson...ended up going into Mt Sinai harbor. NOTE: Entering Sinai at night with a strong current and gust to 30 for the first time can make for a surprisingly entertaining time. ;-) All was fine but those are some impressive sand bars in there!

Cheers
Only been in to Mt Sinai once, many years ago, but in clear weather with light winds. Pt. Jeff is only a few miles away and many more options for mooring and anchoring so that's my usual stop. Sorry the weather didn't cooperate for you. As you said, falling off to a CT harbor would have been the thing to do. Lots of options there, but navigation is critical as there are LOTS of rocks!.

Looks like you've got a couple of good days coming up after the storms today pass through.
 
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