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

[Suijin]

If I were you I would stick to the Sound and sail as far east as you can and return back the same route. A new-to-you 27' boat that you have just refit is, in my opinion, not something you want to take along the south shore, particularly given the fact that there are amazing places to visit in the sound.

The Thimble Islands, on the CT shore, just east of New Haven. Dozens of small granite islands, some of them with just enough room for a single house, with anchorages in between them. A pretty amazing place.

Mystic Seaport. A trip up the river, but you can tie up and spend the day at arguably the best maritime museum in the country.

Essex. Ahhhh, Essex. Gorgeous little town, and the Griswold Inn which is the oldest continuously operating Inn/Pub in the country. Sailors can wear what they want because well, they are sailors.

Cuttyhunk, and Naushon Island. Frozen in time and stunningly beautiful. Keep going and you can put in at Woods Hole (mind the tidal current), Martha's Vineyard, and Nantucket.

Peconic Bay, between the island's forks, has amazingly clear water. Gardiner's Island, Shelter Island, Sag Harbor, and Greenport are all nice towns to visit. The south 2/3 of Shelter are nature preserve and the beach at Smith Cove should satisfy your beach craving unless you want ocean waves.

And Block is lovely.

The trip down the East River is "fun" and awe inspiring, but the whole south shore of the island is pretty pedestrian, IMHO. If I were you I would reverse your plans. Sail up and down the sound for your maiden voyage, and save heading out into the ocean for your next trip.

I grew up in Oyster Bay and my father was a rabid sailor. Our summer vacation each year was taking our leaky Bermuda 30 as far as we could in 3-5 weeks up the Sound and back. Did the circumnavigation one of the first times and we were all "meh" and stuck to the Sound, and beyond, from then on. In general, the wind gets better as you head east that time of year.

As far as navigation apps, the Navionics app is hard to beat. They supply map data to the hardware makers and are seeing the writing on the wall for the future of the industry. I've used it up and down the east coast and it's great. I think it's $35 (I got it when it first came out and was $5) and it's basically the whole east coast.

[hugosalt]

Makes much sense for "get to know your boat cruise" to stay in and around sound. You especially want this to be a good experience, without drama, for your Mrs.
Plum gut can be downright docile if you transit with current,
and you do not want to ever transit with strong opposing wind to current as you have potential for standing waves that you may not see until to late.
Sailing across sound at Port Jeff. in favorable conditions is certainly well below average difficulty rating...concerns
being keeping clear of the ferries, don't fall asleep and
bump into Middle Ground Light, but Stratford Shoal
ok to stop for lunch out of way of traffic.
Ct coast approaches need to be checked carefully as usually not as straight forward as north shore of LI.
Ct. also a few breakwaters if making approaches at night,
New Haven, Duck Island come to mind, are well charted.
When cruising, I usually try to have short and long northern dest. and short and long southern dest. so if wind/crew
act up have a default/alt dest.
If heavy weather out east you could also hang a left going west and spend 2 weeks exploring your nearby waters which include
Northport, Cold Spring Harbor, Oyster Bay, Manhasset Bay, City Is, Norwalk Islands, Greenwich, Mamaroneck.
Seems you will be on the water for the 4th of July, research
some good spots for fireworks beforehand.
Point of info...close to your home waters fireworks every Wed. and Friday night off Rye Playland...unless Westchester county has closed down Rye playland.

[seaturkey]

To all,

You've successfully changed the fate of the maiden voyage of the sea turkey. The little boat that probably can ?

We'll be heading east and exploring in between the forks.. And on the return up to ct to explore the coast that so many of you have spoken so highly of.

Sailing westward down towards city island and then back east to Huntington via manhasset bay...

Gents, sincere thanks to all and I'll keep you all posted -

Cheers

[hugosalt]

Navionics great..use on phone ($14.)for back up and also on tablet...can't say enough...few years ago on cruise to Maine
one by one chartplotter, nobeltec on computer, radar all had their issues..in the end from Cape Cod canal north we used
the $14. Navionics app on phone.

[seaturkey]

Any preference on which one?

Please see attached

[flopresti]

Hi Seaturkey, you'll have a great time. You got lots of good advice. Remember the harbors mentioned in the Sound. (forgive me if I repeat.. I'm just seconding)Behind Shelter Island, Greenport is good for a few days. Nice beaches, inlets. Around Fishers Island. Stopping on Fishers Island is a blast. If you have kids, go up Mystic River to the Museum.

I wouldn't think of entering anyplace on the South Shore without a calm and local knowledge - if you get in a blow with a 27'er on the South Shore, go downwind (back to NY Harbor if you must). Personally, I wouldn't think of entering a harbor on the S. Shore in a blow.

I would use a scopalimine patch on the S. Shore - the Sound is so much calmer. (You can't get seasick - your the skipper. ) Much younger, I did it in a Catalina 25' without an engine (the outboard got dunked 1/2 way up the S. Shore going East) & I sailed into Newport & learned a lot. (I radioed the Coast Guard and they asked me if I was sinking - I said "No" and they said something like, "keep sailing".


Enjoy. Personally, with a 27'er (when I did it I had a 25 year old as crew who had sailed a small boat around the world after high-school). So with a 27'er I would go up the Sound and hang out in Shelter I, perhaps jump to Block , perhaps go into Newport. Hang out in Shelter I., then sail back past Huntington and into NY Harbor and perhaps up the Hudson to West Point. Drop anchor around Manhattan, Hudson at 100th street, anchor near the Tapanzee. You can go under the Verranzano and duck into Keyport YC, free for one night for visitors... Enjoy,

I guess I wouldn't do S.Shore on your boat without a crew like I had...(and I was younger) Frank

[anotherT34C]

IMO, no need to be scared off of the south shore. Fire Island Inlet was just dredged last year, follow the buoys straight in. If you do go in there, instead of dropping anchor off to the west of Kismet, I'd go a bit farther east and drop a hook just east of Atlantique. There's a deep hole there (it's on the charts) next to the marina where you can anchor a few yards off of the beach in a very protected cove with a muddy bottom. Dinghy to Kismet, or take the water taxi from Atlantique. Next, I'd skip Moriches inlet and run straight to Shinnecock. If you leave FII at slack after high, you'll hit Shinnecock about 10 hours later. Anchor east of the fishing fleet (plenty of water for you). There are a few restaurants to hit (not much else... it's just a refueling waystation). Make sure you leave Shinnecock at slack tide. Major rollers will keep you inside otherwise. From there, Block is just another 10-12 hours away.

Between the forks, there's a nice town mooring field east of Greenport. Last year, it was $1/foot and included use of the shower facilities in town. Look for a mooring with a plastic bag with some papers in it, that's a transient.

Coecles Harbor (east side of Shelter Island) is not to be missed. The approach is one of the most frightening (narrow!) but the anchorage is one of the nicest you'll find anywhere. Best dinner we ever had on Earth was at the Ram's Head Inn. Over at the marina (west side), say hi to Billy Joel on your way to the showers. He's often hanging about.

[SailFastTri]

My $.02 on some of the further posts:

IMHO the Thimbles are overrated. No shore access. It's a crappy anchorage loaded with granite hazards, exposed to the prevailing SW wind fetch the entire width of LIS, and the bottom is foul with *live* and dead power cables and abandoned mooring chains. Nice to motor through one time at slow speed to see the little island houses and move on.

Other than that I agree with other advice, except Cuttyhunk and Newport are going to stretch your range in the 2 weeks you have -- why push for the distance when there are so many great places to explore in LIS, BI Sound, and Gardiner's Bay areas?

Also -- In LIS (for flat water) I'd favor the CT shore if you get a cold front (strong NW winds) and the LI shore in SW winds if strong. In east winds (usually accompanied by cooler wet weather for a couple of days) I'd stay put during the ebb (wind against current) and depending on how much wind/rain perhaps hunker down in a harbor where there's things to do ashore.

Wishing you a great adventure, and hoping nothing breaks.

[Jbingham]

We did the trip last year through hells gate at slack tide. Then hit Greenwich CT town docks, old saybrook marina, transient stop at fisher island (snobby but great harbor to look at) block island (oar restaurant was awesome and a fun stop in general), Martha's Vineyard (we skipped cuttyhunk but a must stop for you and then continued on to Nantucket. Martha's Vineyard and Nantucket are off your mark for the sound but great spots!

[hellosailor]

"Do you have any advice on navigation apps for iPads? "
Check out this month's SAIL magazine, where they compared 10 tablet apps and (oops) forgot to mention they really compared nine iPad apps. And accidentally mentioned one for that much larger Android market.

[seaturkey]

Hello All,

Just wanted to thank everyone again and offer an update...

Went sailing this weekend on a pseudo "shakedown"

Had a great time... Until -

Until we were on a close reach, about 13 degrees of heel and BANG

"What the £^c% was that"

After a few confused moments, the bow screamed into irons, the genoa luffed and then pulled the bow into a beam reach in the other direction... The admiral was on the tiller and after a few brief moments of total confusion we she verbalized that the tiller had no authority...

We elected to motor and reef after a 3 second discussion to regain some rudder authority (which worked - thank god) and we got pointed into the wind with the intention to reef the sails. Started to reef the genoa and began cranking on the roller furling... Where it got tougher and tougher to do so -

After inspection of the sail I realized that the 'BANG' we had heard was the forestay shackle snapping open, then during the furling (or the attempted furl) the opened shackle grabbed the gennaker (read spare) halyard and wrapped itself up in it....

Out on the water, gusts to 18 and a roller furling that would only come in a third the way and an admiral with very little experience on the tiller... On Memorial Day weekend :/

No me gusta

After being whipped and beaten by the genoa while I manually wrapped the sail up and securing the mast with the main halyard after dropping the main we limped under power to our raft up and eventually back to port and our mooring.

The point of the story : could I have done anything differently or better?

Ideas?

[seaturkey]

Also wanted to apologize to anyone that witnessed a little blue boat zigzagging across the entrance to Lloyd harbor...

[SailFastTri]

Originally Posted by seaturkey

Hello All,

Just wanted to thank everyone again and offer an update...

Went sailing this weekend on a pseudo "shakedown"

Had a great time... Until -

Until we were on a close reach, about 13 degrees of heel and BANG

"What the £^c% was that"

After a few confused moments, the bow screamed into irons, the genoa luffed and then pulled the bow into a beam reach in the other direction... The admiral was on the tiller and after a few brief moments of total confusion we she verbalized that the tiller had no authority...

We elected to motor and reef after a 3 second discussion to regain some rudder authority (which worked - thank god) and we got pointed into the wind with the intention to reef the sails. Started to reef the genoa and began cranking on the roller furling... Where it got tougher and tougher to do so -

After inspection of the sail I realized that the 'BANG' we had heard was the forestay shackle snapping open, then during the furling (or the attempted furl) the opened shackle grabbed the gennaker (read spare) halyard and wrapped itself up in it....

Out on the water, gusts to 18 and a roller furling that would only come in a third the way and an admiral with very little experience on the tiller... On Memorial Day weekend :/

No me gusta

After being whipped and beaten by the genoa while I manually wrapped the sail up and securing the mast with the main halyard after dropping the main we limped under power to our raft up and eventually back to port and our mooring.

The point of the story : could I have done anything differently or better?

Ideas?

The lesson learned is to always check your halyard tension before furling a headsail. A loose halyard will wrap at the top and then you're in a predicament like you found yourself. The only fix is to have someone go aloft and disconnect to unwrap it. If you have a wire halyard it can take a set from being wrapped tightly on the furler foil, and the wire will then need replacement.

The good news: You won't do this again

[hellosailor]

Done differently? Depends. Why did the shackle open? Did it fail? Was it not seized or secured?

Sounds like you need to do a rigging inspection, and check that everything is in good order. Which is also a good way to keep busy when you find you're stuck on the boat (waiting for whatever) from time to time with nothing to do but wait.

[Stu Jackson]

What kind of shackle?