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Discussion Starter #1
My husband just finished restoring a 1980 23' Crocker Stonehorse. Her relaunch was 1 month ago and we've only really done a 3 hour sail with her. We plan to sail from Sheepshead Bay, New York to Marthas Vineyard next week (yikes!). We plan to do it in 4-5 days with stops on Long Island, Fire Island, Block Island, and Buzzards Bay. If anyone has done this trip I would appreciate any advice. We hope to make 4-5 knots and have charted a decent course but I'm sure there are many things we haven't thought of. Thanks ahead of time!
 

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HANUMAN
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That's an confident itinerary you have going on. Nothing wrong with it, but the time frame is not going to allow you much R&R along the way. You might want to spend more than a couple of hours on Block Island :)

Have you considered going through LI Sound and seeing the sights?

Then again, if you prefer to be underway as much as possible, then I can't fault that. Remember, current is everything and Eldridges is your best friend.

I'm assuming it's not 4-5 days round trip.
 

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Old enough to know better
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Well I have no advice to add, other than it being one of the most beautiful small boats to do it in!
 

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Over Hill Sailing Club
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Have done that trip many times as have lots of folks here. If you have any particular questions, you'll probably get plenty of feedback. Much to think about as far as planning. Going outside, it's a long stretch with few good options if anything goes wrong. If you can only make 4 knots, you may want to go through the Sound.
 
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Discussion Starter #5
Thanks to all! Our boat is currently at Sheepshead Bay so given the time frame, we want to get there as quickly as possibly while still enjoying some sights which is why we decided to sail outside. For people who have done the trip going outside, any specific spots you recommend to stop for the night or a few hours? Is it better to go through Great South Bay and call for the drawbridge or will that take too much time? Our goal is to leave NY early Monday morning and hopefully get to MV by Friday afternoon (yes 5 days one way).
 

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Very ambitious sail. Are you certain that the outside route is actually that much faster? If you time your trip properly with the tidal current, a sail up the East River and through the Hell gate will get a tremendous boost in speed. Similarly at the East End you can get a big push from the current. Of course, if you time it wrong the current is a problem. Given that you are pretty close to Narrows at the start of that trip, I would consider the Sound. If unforeseen problems arise, the route through the Sound gives you many more options.
 

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Hey,

From Sheepshead bay I would definitely go up the east river and then through the sound.

If you go in the ocean there are VERY few places too stop. It can be difficult to get into great south bay and then you need to be back into the ocean to continue past Montauk.

In the sound there are LOTS of harbors to stop on, on both sides. There wont be big waves (unless the wind is from the east).

Good luck,
Barry
 

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Tartan 27' owner
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All of the south shore of LI inlets (Shinnecock, Fire Island, Jones etc) are pretty tricky and potentially dangerous if you hit them at the wrong tide. Local knowledge is strongly advised before tackling any of these inlets. Your first "safe" harbor will be Montauk harbor which is about 120 miles or so, or perhaps 2 full days (and nights) sailing, if sailing east on the outside. You don't have to take my word on this either as you can download coastal pilot #2 which covers these inlets:
http://www.nauticalcharts.noaa.gov/nsd/cpdownload.htm

I am not saying "it can't be done". I am saying that for my first time making a trip like this I would prefer going through the LI Sound where safe anchorages are abundant. The trip up the East River is a blast when the current is with you.

Your life, your boat, your call.
 

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The sound has some of the most delightful sailing around. September is a beautiful time, cooler weather, nice breeze, deep water, and lots of places to take a break.
 

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From Sheepshead Bay, you're not going to lose any time by taking the inside route. On the plus side, you'll have dozens of options on both sides of LIS for protected harbors, mooring fields and anchorages to choose from. Few options going on the outside, and some of those can be tricky depending on the tide (and weather). Going inside also gives you access to plenty of support services and shelter should things not go as planned. Have you and your husband done a trip of this duration before?
 

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We are all sounding like a bunch of safety weinies.

I say go for it.
Well... keep in mind the original poster is new on this forum and is someone we know nothing about in terms of experience, etc. Nobody has said anything that isn't readily apparent on a chart. The OP asked for opinions presumably because they wanted them and weren't 100% confident about going outside.

I would never tell anyone to go for it without knowing for certain they were up to the task. What's the worst that could happen? There's plenty of sad stories to choose from. So yeah, I'm a safety weenie. Guilty as charged. :)
 

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Since this is a new boat to the OP, it would not be a good idea to do a real shakedown on the outside, especially because the inlets to the east are notoriousy treacherous in adverse conditions.

Agree with others who have recommended the LIS route for all the reasons stated. I would also recommend staying inside Fishers Island Sound, minding all the rocks along that way until past Watch Hill Passage.

Minding the Eldridge Tide and Pilot book is an absolute necessity, primarily for timing passages, but also for safety in areas like the Race (south of New London).

Also, I would be surprised if the average speed for a Stonehorse 23 is as high as 4kts, especially there is a dinghy under tow, as the current will not always be fair and favorable winds synchronized with favorable currents is wishful thinking. This sounds like an endurance contest even if the weather is perfect. Making it to BI in 4-5 days would be an accomplishment IMHO.
 

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Bristol 45.5 - AiniA
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I guess I am a safety weinie too - at least for myself. Obviously we have done some challenging passages, but have always weighed the odds. In this case, with a new to me boat I would take the inside passage. If things worked well I might choose the outside passage for the return trip.
 

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Over Hill Sailing Club
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If you can get inside, maybe through Fire Island Inlet (follow a local commercial boat in) into Great South Bay, you can make it out to Gardiner's Bay/Block I. Sound through the Shinnecock Canal. This requires going through Moriches Bay which is notorious for its shoals. I have been through there a number of times with a 3' draft but it needs to be a sunny day with someone up on the bow to spot the sand bars. It's a scenic, interesting trip, going in and around Shelter Island and such but a lot of work. I'd opt for the East River and LI Sound.
 

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That's an ambitious cruise in that timeframe. At 4kts, it must be at least 50 hrs of sailing, probably closer to 75, after tacking/gybing/headwinds/foul current, etc, is my guess. Even 1kt of foul current is going to seriously extend a trip on a 4kt boat. Are you sailing through the night or planning 12 to 15 hour days?

Add me to the chorus of taking the route through the Sound. You could certainly find bad weather and some rough seas over 5 days. You'll need to prepare for a bailout or to be held up. Comes with the territory.

Beautiful time of year for that trip. Crowds are down after Labor Day. Weather is usually warm during the day and cooler at night and the breeze is up. However, storms are storms and they are still around.

When are you going to return to NYC? Unfortunately, weather does start to go downhill fast in Sept.
 

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If you can get inside, maybe through Fire Island Inlet (follow a local commercial boat in) into Great South Bay, you can make it out to Gardiner's Bay/Block I. Sound through the Shinnecock Canal. This requires going through Moriches Bay which is notorious for its shoals. I have been through there a number of times with a 3' draft but it needs to be a sunny day with someone up on the bow to spot the sand bars. It's a scenic, interesting trip, going in and around Shelter Island and such but a lot of work. I'd opt for the East River and LI Sound.
That is a nice route, though chances are it would be a motor job virtually the entire way...

Only problem is, the fixed bridge clearance of only about 21' over the Shinnecock Canal...

:)

I agree with most others, sounds like LI Sound is the better way for these folks to go...
 

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If you can get inside, maybe through Fire Island Inlet (follow a local commercial boat in) into Great South Bay, you can make it out to Gardiner's Bay/Block I. Sound through the Shinnecock Canal. This requires going through Moriches Bay which is notorious for its shoals. I have been through there a number of times with a 3' draft but it needs to be a sunny day with someone up on the bow to spot the sand bars. It's a scenic, interesting trip, going in and around Shelter Island and such but a lot of work. I'd opt for the East River and LI Sound.
There are 3 problems with the inside-the-barrier-island route. 1.) shallow water, particulary at the east end of Great South Bay and in Moriches Bay. 2.) there are several draw bridges to deal with and the reversing currents can be a challenge for a sailboat if not timed correctly (you will not be able to hold a fair current all the time). 3.) There is a 25' fixed bridge clearance in the Shinnecock canal, requiring you to remove your mast and restep it (assuming the gin poles are still there). Agree with smurphny's conclusion about the scenic part, though.
 

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Over Hill Sailing Club
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Oops. Have only gone that way in powerboats so didn't even think about the clearance.
 

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You are getting good advice to go inside. You should consider at least Moriches and Shinnicock inlets as un-navigatable. Even after rounding Montauk Point, if you are looking for rest or shelter you have to sail to the harbor which is a couple of hours to the west. Then you'll lose another couple of hours going back East when you leave.
If you go inside to, say, Oyster Bay, then Mattituck or Essex Ct., and on the BI. Sail with the current as much as possible. That will be a memorable trip. The outside route will be an endurance ordeal.
 
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