Sailing around Long Island in two weeks... Starting in Huntington... How would you do

[seaturkey]

Hello All...

Planning a trip in late June through early July. Planning to sail around Long Island... No specific timeline to be anywhere or do anything specific...

Any pointers or ideas on the planning, docks, moorings, beaches etc would be greatly appreciated...

Only "must" is a 3 day stop off Kismit (bayside obviously) to enjoy the beach a little...

[hugosalt]

Welcome aboard!
Good to hear you do not have to adhere to a specific timeline/schedule. Makes for a safe cruise.
planning....Would make sense circumnavigating island
counter-clockwise...west to east on ocean side as this will give you better odds that wind will be with you while in ocean.
Are you familiar with Long Island south coast inlets?
A long stretch to go without a lot of options, need a good
weather window.
They are not always inviting in the best of conditions,
often moving shoals. assuming you will be entering Fire
Island Inlet to spend time at Kismit. How much do you draw?
If you time it right you will be able to ride the current
down the East River and into the lower bay.
You want to pass hell Gate with a favorable current or slack water.
Also, be sure to time rounding Orient Pt./Plum Gut with the current.
A few good places to stop...
Steppingstone Marina (my marina) just west of Manhasset Bay
on the sound, good for waiting to go down East River...if interest
I will arrange mooring n/c.
Or in Manhasset bay...town moorings free for 1st 48 hrs.
(the yellow ones, lining the channel) on 1st come basis
seems always some available, bring your boat hook and a pair of rubber gloves.
Atlantic Highlands... moorings near Sandy Hook.
As you come ito the sound...
Ct. River village of Essex right on the river, wooden boat museum, great all around.
Mattituck Inlet back on L.I. side..very protected at south
end, walking distance to town. Can anchor or Matt-a-Mar marina.
Thinking you know Port Jefferson, can anchor, moorings,
great town on the water.
Hope this helps,
Hugo

[seaturkey]

I am absolutely interested in all you had to say...and offer. Have a 1982 Tanzer 27 that I basically just rebuilt top to bottom and outside of a few harbor hops, this will essentially be her maiden voyage.

I am very familiar with fire island inlet as, (in a previous life) I used to be a south shore power boater... I'm sorry -

Spent the last few boat less years driving to Robert Moses and making the walk to kismit so this is the closure the admiral and I were looking for...

Not overly familiar with the voyage en'large as I'm new to the north shore in general.. As well as the east river, and the sail through plum gut... I've done what I consider to be a decent amount of research but am aware I'm still a novice and am looking for any advice tips anyone with local knowledge has to offer...

...btw: she draws 5' on a bad day after a steak dinner ...

I'm also concerned about stepping the mast to get through the locks vs rounding Montauk..

Cheers!

dl

[Rick01541]

Better winds and places to go if you continue north to Block Island, Narragansett Bay and Buzzards Bay rather than going around Long Island.

[seaturkey]

That's the next trip... Have another two weeks in late July into August and block, newport and the rest of the cape is on the agenda.

This is a "get to know your boat" cruise as she's still new to us... Before I go offshore a bit I figured the round Long Island trip should present us with enough challenges while still maintaining an adequate margin of safety...

[Curmudgeon]

It's safer to go north. There are very few places to duck in on the South shore of LI and with the prevailing SW winds it's a lee shore. Montauk can also be challenging in a 27 ft. sailboat.

[seaturkey]

Can you elaborate on "go north" ?

[Curmudgeon]

Originally Posted by seaturkey

Can you elaborate on "go north" ?

Do what Rick01541 said.

[SailFastTri]

Just to add some thoughts to prior posts: You could easily spend 4+ days in the Gardiners Bay Area harbor hopping. Great daysailing in protected waters, and there's 3-mile harbor, Shelter Island (3 great harbors), Sag harbor, Greenport, Orient harbor, or head into Paconic.

When in LIS don't overlook the CT shore, and it's many harbors. Most important - work the winds and avoid wind-against-current situations which can beat you up with short chop... especially in headwinds.

[seaturkey]

Thank you sail fast... More of what I was looking for... I live on the island, and I'm familiar with the area and the ports, most of which you just mentioned, but from a land perspective... I've driven to greenport, orient and shelter island.. HALF THE REASON WERE TRYING TO PLAN THE TRIP! We've hit most of them on drives to the vineyards and such.

So I thank you good sir for pointing out that these places are indeed worthy of visiting with the boat... And not just the drive -

The allure of boating to some of the places we've visited is basically what prompted the idea of buying the boat in the first place.

All that being said, what are your thoughts on routing, anchorages and moorings etc... Even maybe some of the gotchas that a nube like me could end up getting into... Any info from experiences or general knowledge is worth it's weight in platinum...

I'm open to comments, suggestions and/or threats

Also, any idea why going offshore may be the "safer" play as some others pointed out?

I was planning a trip "up north" in August after I had some coastal cruising under my belt... Should I flip the trips ?

[Sandero]

Huntington
Lunch stop in Pt Jef... anchor up west of the channel behind the beach
sail to Thimbles on CT side... pick up a mooring for the evening.
Through Plum gut anchor in front of the windmill off Gardiner's Island.
Then head to 3 mil harbor for the evening... good anchorage well protected
Sail to Sag for Lunch and a tour
Head west around Shelter Island and moor in Dering Harbor or across in Stirling harbor. Dering quiet.. Greenport a lively (tourist town in walking distance)
Montauk Harbor for lunch

Don't know the south shore.

[seaturkey]

I love it - thank you.

So you're saying to start out headed East...

How is the sail across the sound from Pt Jeff? I know it depends on conditions almost entirely but would you give it an average difficulty rating?

Also, is plum gut as challenging as I've heard?

[Stu Jackson]

Originally Posted by seaturkey

I was planning a trip "up north" in August after I had some coastal cruising under my belt... Should I flip the trips ?

Given your limited experience, a new boat and the questions you're asking, yes, that's what I'd do.

Fair winds, safe journey.

[SailFastTri]

Originally Posted by seaturkey

Thank you sail fast... More of what I was looking for... I live on the island, and I'm familiar with the area and the ports, most of which you just mentioned, but from a land perspective... I've driven to greenport, orient and shelter island.. HALF THE REASON WERE TRYING TO PLAN THE TRIP! We've hit most of them on drives to the vineyards and such.

So I thank you good sir for pointing out that these places are indeed worthy of visiting with the boat... And not just the drive -

The allure of boating to some of the places we've visited is basically what prompted the idea of buying the boat in the first place.

All that being said, what are your thoughts on routing, anchorages and moorings etc... Even maybe some of the gotchas that a nube like me could end up getting into... Any info from experiences or general knowledge is worth it's weight in platinum...

I'm open to comments, suggestions and/or threats

Also, any idea why going offshore may be the "safer" play as some others pointed out?

I was planning a trip "up north" in August after I had some coastal cruising under my belt... Should I flip the trips ?

I might have missed it but what's your starting point?

If I were you I'd play it by ear and harbor-hop based on the 3-day forecast. As I wrote above, plan your days around the winds and currents. If extended rain is forecast plan to be somewhere that has shore-side attractions so you can get off the boat for a few hours at a time, even if you need to pay for cabs -- it beats cabin fever.

I've been to all of these harbors enough times that I couldn't give you a definite count, but you should do your own exploring. Check out cruising guides and ActiveCaptain.com and do your own thinking too by looking at the charts and deciding where you want to explore.

You didn't mention if you have a dinghy but that will affect some of your choices -- without a dinghy you'll want to find a dock or a mooring with launch services available. In less developed harbors you'll be on your own to get ashore.

People here will offer suggestions but your best decisions will be made under the circumstances that will be largely determined by the weather and your boat's speed. (I always find it a bit humorous when making a reservation and they ask about arrival time, after I've already told them it's a sailboat). Sailboats and schedules don't play well together. I give them a time anyway because they need it, but will call again if running later.

[seaturkey]

Thank you again Sailfast...

Starting point is Huntington... Have a mooring there. We do have a ehhh "dinghy." Of sorts at least -

This thing was a essentially a bottom to top restoration (the restoration is done now and I'm 60% of the way through the list of improvements I wanted to make) and the budget was approaching the pain threshold when the 'dinghy decision' was made... In any case - we're not entirely dependent on a launch... Though I can safely say it's preferred -

I love the advice - likely the best I've gotten so far.

I spoke to the admiral re: what you said and I think that is exactly what we're going to do and how we're going to do it.

Do you have any advice on navigation apps for iPads? West marine was pushing NobelTec and MaxSea (both time zero products) so I downloaded them both... And they appear identical... Before I start buying $40 charts (required) for them (also not sure if they'll share the charts or if I'd have to buy two of the same chart for each app, etc) I wanted to know if you have any preferences, or you've heard of something along the lines that world well -

Again thanks for everything thus far