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Goodwind90 07-19-2016 05:41 PM

Sailor from Long Island
 
1 Attachment(s)
Hello Sailors!

I'm new to Sailnet and looking forward to getting involved with some sailing discussions and more excited to learn from all you veteran sailors out there!

I'm 26 years old and have been sailing since I was in diapers on my father's Cape Dory 27. Growing up, I raced dinghies (opti's, blue jays, 420's, lasers) at my local yacht club in the Great South Bay, NY. The summer I graduated high school, I became addicted to windsurfing and that completely took over my life, until now. My father sold the Cape Dory to his brother about 10 years ago and bought a 1989 Tartan 28, fixed it up, and raced it for several years, but never went on long cruises. Two years ago, he decided to purchase a Sabre 34 and sell the Tartan. With my new job as a construction project manager, a few years out of college with some money in my pocket, I decided to jump at the opportunity of interest-free financing on a boat that I knew was impeccably maintained for years. So, here I am, my second summer with the boat and I'm now obsessed with cruising. My girlfriend and I have done a few over-nighters on the bay with one 4-day trip last summer and we absolutely love the lifestyle. Owning this boat has truly changed my life for the better. We spent the winter watching youtube videos of cruisers sailing around the world (Sailing LaVagabonde is our favorite) and we aspire to experience that adventure some day as well! I am now re-evaluating my career choices to find the best way to achieve this lifestyle some day as well.

I'm currently planning a trip from my home port through Fire Island inlet to Block Island, then Newport, then west to NYC, and back home, stopping along the way at different ports and harbors for the nights. If anyone has some experience sailing this route and can offer some advice, I would greatly appreciate it. I have charts, Eldridge book, nav tools, a handheld GPS, VHF, and basic nav skills. It's a big step from my little bay that I grew up in, but it's something I need to do.


Cheers and Happy Sailing!

-Chris

CalebD 07-19-2016 07:00 PM

Re: Sailor from Long Island
 
Welcome to SailNut Chris.

You have a nice boat to start out your cruising adventures. Your itinerary sounds infinitely do-able and you'll probably have a blast doing it. The is a whole great world out there beyond the GSB.
You probably already know this but timing your exit at FI Inlet to the tides is a good idea. You probably also have anchors and all the rest of required safety gear.

Be safe, have fun.

JimsCAL 07-19-2016 08:27 PM

Re: Sailor from Long Island
 
Toughest part of that trip is the first leg. Once you exit the Fire Island inlet, there's really no easy place to stop in bad weather until you get to Montauk.

Enjoy the trip.

RobGallagher 07-19-2016 08:55 PM

Re: Sailor from Long Island
 
The wind, prevailing from the SW will undoubtedly swing around and be on the nose for the duration of your trip out. Your return trip will undoubtedly encounter winds from the WSW.

Make all your plans, prayers, chants, set all your tide and weather apps, chart plotters, etc. as if you are headed to Atlantic City then turn left as you exit the harbor. It's your only chance of sailing when cruising.

:)

SanderO 07-20-2016 06:10 AM

Re: Sailor from Long Island
 
I would consider moving your home port to the north shore... I think the mini cruising opportunities are better from there as a starting point. But if you have the time and hit up some of the harbors on this cruise you'll figure that out. Perhaps start with a home port in Oyster Bay, Cold Springs, Huntington, NPT or Pt Jef. Then maybe move to the East End... Greenport, Three Mile, Sag Hbr, Dering Hbr... The East end is a great jump off point to Narragansett, Block, Martha's Vinyard, Cap Cod and Natucket. Great South Bay is not really good for mini cruising. I've sailed this region since 85 and this is my advice.

If you live mid Island obviously you have to drive a but to get to the boat. Not a big deal except dealing with Hampton traffic. Spending a bit of time getting to your boat in a great location is much more important than driving 10 minutes to a boat located in a crappy sailing area. I know many sailors who kept their boat in the East End and drove from NY or even NJ... for just the reason that the sailing / cruising is much better out east for multiple reasons.

Your first planned trip is a perfect example of the down side to home porting in the Great South Bay... sailing east is pretty long sail without any place to duck in and it a lee shore too. You also can visit the various harbors by car and check them out before sailing to them or arranging for a seasonal summer spot. You can even find decent in water winter storage and extend you sailing season as most moorings are pulled.

Finally I would recommend you get a seasonal mooring NOT a seasonal slip. Living aboard on the mooring is way more pleasant than trying to live in a parking space in marinas usually filled with power boaters. But you'll need a dink to get to your boat and again this is more like the "cruising lifestyle" then going from marina slip to marina slip. You learn to anchor well and avoid the cost of moorings as well. In 31 years of cruising LIS and Southern New England the only transient mooring I think we paid for was in Edgartown. Unfortunately some harbors are so crowded with moorings (Huntington, Dering Hbr).... you are required to anchor pretty far from shore... but that has its advantages as well.

Good luck! Watch out for the idiots who don't stand watch and are letting GPS drive their boat's auto pilot. Sadly this is becoming very very very common in this region.

BarryL 07-20-2016 01:02 PM

Re: Sailor from Long Island
 
Hey,

Welcome.

I'm a little confused - are you planning on doing this trip in one short, or over the entire summer? The circumnavigation of Long Island as you have listed it is probably around 300 nm. How long do you think this will take?

The Long Island sound is a very rich cruising ground. Between the CT and LI sides there are probably harbors every 5-10 miles. The only real exception to this is the Long Island side between Mt. Sinai and Mattituck - thats about 20 nm with no harbors in between. On the CT side there are still plenty of harbors.

Anyway, if you haven't been there, you should look into Active Captain. The problem with the LIS is that there are SO many marinas and harbors that making a decision on which ones to see is the real challenge. You can anchor out, hang on a mooring, stay in a bare bones marina, or one that is more like a country club.

Good luck,
Barry

Goodwind90 07-20-2016 01:08 PM

Re: Sailor from Long Island
 
Quote:

Originally Posted by SanderO (Post 3586241)
I would consider moving your home port to the north shore... I think the mini cruising opportunities are better from there as a starting point. But if you have the time and hit up some of the harbors on this cruise you'll figure that out. Perhaps start with a home port in Oyster Bay, Cold Springs, Huntington, NPT or Pt Jef. Then maybe move to the East End... Greenport, Three Mile, Sag Hbr, Dering Hbr... The East end is a great jump off point to Narragansett, Block, Martha's Vinyard, Cap Cod and Natucket. Great South Bay is not really good for mini cruising. I've sailed this region since 85 and this is my advice.

If you live mid Island obviously you have to drive a but to get to the boat. Not a big deal except dealing with Hampton traffic. Spending a bit of time getting to your boat in a great location is much more important than driving 10 minutes to a boat located in a crappy sailing area. I know many sailors who kept their boat in the East End and drove from NY or even NJ... for just the reason that the sailing / cruising is much better out east for multiple reasons.

Your first planned trip is a perfect example of the down side to home porting in the Great South Bay... sailing east is pretty long sail without any place to duck in and it a lee shore too. You also can visit the various harbors by car and check them out before sailing to them or arranging for a seasonal summer spot. You can even find decent in water winter storage and extend you sailing season as most moorings are pulled.

Finally I would recommend you get a seasonal mooring NOT a seasonal slip. Living aboard on the mooring is way more pleasant than trying to live in a parking space in marinas usually filled with power boaters. But you'll need a dink to get to your boat and again this is more like the "cruising lifestyle" then going from marina slip to marina slip. You learn to anchor well and avoid the cost of moorings as well. In 31 years of cruising LIS and Southern New England the only transient mooring I think we paid for was in Edgartown. Unfortunately some harbors are so crowded with moorings (Huntington, Dering Hbr).... you are required to anchor pretty far from shore... but that has its advantages as well.

Good luck! Watch out for the idiots who don't stand watch and are letting GPS drive their boat's auto pilot. Sadly this is becoming very very very common in this region.


Thank you, Sander0, for all the useful advice. I definitely see the advantages of a north shore home port for cruising and will definitely consider a mooring when the time comes! I understand the GSB isn't ideal for mini cruising because it takes me about 2 hours to get to the inlet from my dock in Babylon, but for now I need to work with what I have. The prevailing SW winds in the summer for day sailing is what I've grown accustomed to and since I currently live within walking distance to my boat, perhaps when I upgrade to a larger yacht, I will move to the North shore.

As for my planned trip, I was going to try to plan to leave as early as possible in the right conditions to make it to Montauk by the end of the day. If that seems unlikely, I have already scoped out Shinecock Inlet by car and spoke to a few sailors who have tucked in there for the night. Once I get to the east end, it should be fairly smooth sailing to my various destinations until I start to approach NYC on my way back around. I'll have to do my research for where to stay each night along the way (Port Jeff, Cold Spring, Oyster Bay, etc.) and that sounds fairly simple. The part that I'm a little anxious about is heading down the east river (with the tide, of course) and finding a place to anchor in NY Harbor. It would be nice to spend the night at an anchorage where I could overlook Manhattan and then leave in the morning (weather depending) for my last leg back home. Do you have any advice for this part?

Thanks again!
-Chris

Goodwind90 07-20-2016 01:21 PM

Re: Sailor from Long Island
 
Quote:

Originally Posted by BarryL (Post 3586961)
Hey,

Welcome.

I'm a little confused - are you planning on doing this trip in one short, or over the entire summer? The circumnavigation of Long Island as you have listed it is probably around 300 nm. How long do you think this will take?

The Long Island sound is a very rich cruising ground. Between the CT and LI sides there are probably harbors every 5-10 miles. The only real exception to this is the Long Island side between Mt. Sinai and Mattituck - thats about 20 nm with no harbors in between. On the CT side there are still plenty of harbors.

Anyway, if you haven't been there, you should look into Active Captain. The problem with the LIS is that there are SO many marinas and harbors that making a decision on which ones to see is the real challenge. You can anchor out, hang on a mooring, stay in a bare bones marina, or one that is more like a country club.

Good luck,
Barry


Hi Barry,

MY plan is to take a full week off of work so I can try to do the whole trip in 9 days. Do you think that's too ambitious?

The Active Captain site is a great tool and I plan on utilizing it, but I also wanted to see if anyone on here could provide any suggestions for this first time around. For instance, should I stay in Manhasset Bay, Hemstead bay, or Little Neck Bay before my trip to NY Harbor? Should I anchor at Ellis Island or closer to Staten Island before my final leg back to Fire Island? Am I overthinking this? I'm sure a lot of these decisions will be made on the fly based on the conditions and my timing. I just want to make sure I'm as prepared as possible for this trip.

Thanks for your insight, Barry!

SanderO 07-20-2016 04:03 PM

Re: Sailor from Long Island
 
When the time is right you will move your homeport... 2 hrs out and 2 hrs will be better spent driving a bit to the north shore. Most harbors on the Sound take some time to get out... but nothing like that!

Going west from BI... my suggestions are:

Sail a lovely reach to Watch Hill and they stop for the night in Stonnington. Fabulous little town.
From Stonnington... you can visit Mystic... a short way to the west and West Harbor is nice anchorage on Fishers. Good holding bottom in these three (BI has a lot of eel grass!)

From west end of FI sound... sail along the north side... perhaps duck in to Saybrook and you can sail up to Essex. Old Lyme has a fabulous boat yard... small and all sailboats. Walk to a shopping center.

Sail on the north side of LI shoal and head for the Thimbles... you can anchor or take one of the 5 or 6 moorings. Very cool anchorage... between a bunch of tiny private islands.

Next sail to Port Jef. Anchor on the east or west side of the channel. (I anchor on the east up close to the beach) good holding too. If you have a dink... check out Seatauket... or motor over to the Pt Jef town pier and tie along side (free) and visit Pt Jef. Nice town. Too bad they sited their power plant in the harbor.

Next you can check out Northport and Huntington and maybe anchor inside of Eaton's neck for a lunch stop. Great spot. You can anchor far out at NPT or pay for a transient mooring... or tie over night at the town pier... cheap. Super town lots going on there. Copenhagen Bakery is fabulous...

Next Huntington... transient moorings only IIRC.

Next Cold Spring Harbor and Oyster Bay. CSH is nicer to stay on the hook.

10 miles across the sound is South Norwalk... and the islands where you can anchor...

Then you might want to visit port Washington after rounding Sands Point... or anchor off (or rent a mooring at City Island.) The west side you can see the Throgs neck and Manhattan beyond.

Plan you run down the East River... You have to go in a fair or slack tide... There are a few docks on Manhattan and in Queens if you want.

Then you sail out of NY Harbor to the Atlantic and back to the GSB. Maybe anchor in Staten Island (never done it).

You can use Navionics on a mobile device... works fine.

JimsCAL 07-20-2016 04:27 PM

Re: Sailor from Long Island
 
Nine days is ambitious. You will be going a lot of sailing (or motoring) and not a lot of time spent enjoying the harbors you visit. I have been cruising the waters of Long Island Sound and southern New England for almost 40 years. As I have gotten older (and hopefully wiser) I have decided that taking it more leisurely is what I enjoy. I'll spend a few days in a place I like (like Block Island or Watch Hill) and make short hops especially when the wind and weather are not cooperating.

If you only have 9 days, consider a hop out to Montauk, then spend some time exploring places like Block Island, Shelter Island and Newport, and then head home.


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