# Sailor from Long Island



## Goodwind90 (Jul 19, 2016)

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


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## CalebD (Jan 11, 2008)

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.


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## JimsCAL (May 23, 2007)

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.


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## RobGallagher (Aug 22, 2001)

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.


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## SanderO (Jul 12, 2007)

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.


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## BarryL (Aug 21, 2003)

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


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## Goodwind90 (Jul 19, 2016)

SanderO said:


> 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.
> 
> ...


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


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## Goodwind90 (Jul 19, 2016)

BarryL said:


> Hey,
> 
> Welcome.
> 
> ...


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!


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## SanderO (Jul 12, 2007)

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.


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## JimsCAL (May 23, 2007)

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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## SanderO (Jul 12, 2007)

JimsCAL said:


> 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 water of Long Island Sound and southern New England for almost 40 years. As I gotten older (and hopefully wiser) I have decided that taking it more leisurely is what I enjoy. 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 at hop out to Montauk, then spend some time exploring places like Block Island, Shelter Island and Newport, and then head home.


This is spot on advice... you're talking probably 300 miles for the total journey without tacking and entering and exiting harbors... If you sail 6 days... that's 50 per day... and at average 4 knots that's 12 hrs each leg and that only leave 3 days ashore. Cruising is not just sailing... but enjoying the destinations... and there is some nice stuff on LIS to see.


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## BarryL (Aug 21, 2003)

Hey,

I agree with the other guys. For a week, your plans are too ambitious. I think that sailing to Block is a good destination. I would then head west and check out Garndiners bay - orient, Greenport, Montauk, Shelter island, etc.

A few comments - Don't stay at Orient By The Sea - it's too small. In greenport, I've stayed at Townsend Manor and it was great. I've also stayed at Montauk Yacht Club - great place but expensive.

Good luck,
Barry


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## Goodwind90 (Jul 19, 2016)

Sander0, JimsCaL, and BarryL, I cannot thank you guys enough for the helpful advice! This is exactly why I joined and posted- to get valuable insight from experienced cruisers. Considering your advice, I have decided to taper back my plans a bit and save the NYC part for next year. My new plan is to sail to Montauk Lake, Block Island, Jamestown RI (a friend lives there), and then backtrack home. This way, I'll have plenty of time to enjoy each destination and adjust plans based on weather. 

Sander0, thank you for all the information on the harbors and ports. I will be referencing this thread for the information in your post for some time!

Thanks again!

-Chris


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## baywater (Sep 27, 2011)

hi Chris your new itinerary sounds much more doable. Ive done the Block Island and Montauk runs from Babylon at different times and my favorite format now is to cruise near the inlet the evening before leaving and sleep on the hook inside Sore Thumb or grab a berth in the State Park boat BASIN AT Robert Moses. The boat basin is rarely busy often nearly empty. 

Sent from my SAMSUNG-SGH-I317 using Tapatalk


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## Goodwind90 (Jul 19, 2016)

baywater said:


> hi Chris your new itinerary sounds much more doable. Ive done the Block Island and Montauk runs from Babylon at different times and my favorite format now is to cruise near the inlet the evening before leaving and sleep on the hook inside Sore Thumb or grab a berth in the State Park boat BASIN AT Robert Moses. The boat basin is rarely busy often nearly empty.
> 
> Sent from my SAMSUNG-SGH-I317 using Tapatalk


Baywater, thanks for the advice! I've seen sailors stay overnight at Sore Thumb and depart early in the morning to save time. I will definitely be doing that as well. I used to stay overnight there on my grandfathers 1960-something Tartan 27 when I was a little boy so it will surely bring back some great memories


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## baywater (Sep 27, 2011)

me too...

Sent from my SAMSUNG-SGH-I317 using Tapatalk


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## SanderO (Jul 12, 2007)

Goodwind90 said:


> Sander0, thank you for all the information on the harbors and ports. I will be referencing this thread for the information in your post for some time!
> 
> Thanks again!
> 
> -Chris


Chris... feel free to contact me via PM and then phone or meet me in NPT and we can discuss all manner of sail related things and LIS etc.


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## GMC (Sep 14, 2009)

Sounds like you've got a good adventure planned. It looks like your modified plan still has you doing a lot of sailing, which is what it is all about, but like an earlier post, I've been tending to put my long sails in at the beginning and end and stay/cruise in sort of a defined area. I don't know LI yet (I sail out of New Bedford), but I went to a wedding out in Sag Harbor area and it seems to me there is a good week's worth of sailing/cruising in that Gardiner's Bay, Peconic Bay, Montauk, Greenport area alone. I sail with my wife, who has limited interest in long passages. Earlier this summer, we sailed down to Newport. It took about 7 hours with the conditions. Once we got to Narragansett Bay, she was not participating in anything but hops between harbors in the bay for a week. It seems we could spend a summer in that bay and not see it all. My only point is, I've been there with the need to get out there put the miles in and see as many places as possible, but that east end of Long Island might satisfy your first long trip and not burn anyone out. By the way, almost no one ever reports back after a post like yours, so if you are inclined, let us know how it went.


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## GMC (Sep 14, 2009)

As an aside, I use a couple handheld Garmins in conjunction with Opencpn. For planning, Opencpn is great for hundreds of reasons, which you'll see if you check it out. If you've got the right cables, you can set your waypoints and routes on Opencpn and transfer right over to you handheld. Not the only product like that, but it is free and comprehensive.


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## davidpm (Oct 22, 2007)

I have a mooring no one is using so far this summer.

If is off the coast of Madison, CT near Tuxis Island.

Let me know if you need exact directions.


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## CalebD (Jan 11, 2008)

Oh, and keep a watchful eye out for whales in Long Island Sound and the Atlantic. They are around. I believe that the CG has added a whale warning in the notice to mariners for our local waters.

Dead Whale, Struck by Ship Days Ago, Resurfaces in Hudson River | NBC New York

We saw a Humpback in LI Sound last September.


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## Goodwind90 (Jul 19, 2016)

GMC said:


> Sounds like you've got a good adventure planned. It looks like your modified plan still has you doing a lot of sailing, which is what it is all about, but like an earlier post, I've been tending to put my long sails in at the beginning and end and stay/cruise in sort of a defined area. I don't know LI yet (I sail out of New Bedford), but I went to a wedding out in Sag Harbor area and it seems to me there is a good week's worth of sailing/cruising in that Gardiner's Bay, Peconic Bay, Montauk, Greenport area alone. I sail with my wife, who has limited interest in long passages. Earlier this summer, we sailed down to Newport. It took about 7 hours with the conditions. Once we got to Narragansett Bay, she was not participating in anything but hops between harbors in the bay for a week. It seems we could spend a summer in that bay and not see it all. My only point is, I've been there with the need to get out there put the miles in and see as many places as possible, but that east end of Long Island might satisfy your first long trip and not burn anyone out. By the way, almost no one ever reports back after a post like yours, so if you are inclined, let us know how it went.





GMC said:


> As an aside, I use a couple handheld Garmins in conjunction with Opencpn. For planning, Opencpn is great for hundreds of reasons, which you'll see if you check it out. If you've got the right cables, you can set your waypoints and routes on Opencpn and transfer right over to you handheld. Not the only product like that, but it is free and comprehensive.


GMC, I really appreciate your input and advice. My girlfriend and I are definitely looking forward to the long sails as well as anchoring at each destination to explore and relax. I know I'll be in some great day sailing areas which would be great to explore during the trip, but I may need to save that for the next one with the limited time that I have. I have a goal in mind, which is to sail to Jamestown or Newport from Block Island with my friend who lives in Jamestown, so I'm willing to sacrifice some day sailing to achieve this goal. This will undoubtedly be the first of many cruises for me in that area, so I'll have plenty to explore next time  And I will definitely report back after my trip; it's the least I could do for everyone who has responded to this thread!

That OpenCPN application seems like an invaluable tool at first glance! I will surely be playing around with this over the weekend and utilizing it for my trip. Thanks again, GMC! I'll be contacting you when I sail to Buzzard's Bay one day!


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## Goodwind90 (Jul 19, 2016)

davidpm said:


> I have a mooring no one is using so far this summer.
> 
> If is off the coast of Madison, CT near Tuxis Island.
> 
> Let me know if you need exact directions.


Davidpm, thanks a lot for the offer! Not sure if I will in that area for this trip, but I will keep you in mind for future trips!


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## Goodwind90 (Jul 19, 2016)

CalebD said:


> Oh, and keep a watchful eye out for whales in Long Island Sound and the Atlantic. They are around. I believe that the CG has added a whale warning in the notice to mariners for our local waters.
> 
> We saw a Humpback in LI Sound last September.


I will keep a lookout for whales! Would love to witness a breach! Thanks CalebD!


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## captbill2209 (Feb 16, 2016)

Sounds like a great trip! very jealous, if you ever need a crew Im 26 and in the construction industry also. Live in massapequa , boat is in Napeague Harbor. Enjoy the trip and post pictures when you return.


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## Goodwind90 (Jul 19, 2016)

captbill2209 said:


> Sounds like a great trip! very jealous, if you ever need a crew Im 26 and in the construction industry also. Live in massapequa , boat is in Napeague Harbor. Enjoy the trip and post pictures when you return.


Always looking to meet new sailors and enjoy the bay! PM me and we'll set something up! Napeague is far! I've windsurfed there a few times.


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## Goodwind90 (Jul 19, 2016)

CalebD said:


> 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.
> ...





JimsCAL said:


> 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 said:


> 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.





BarryL said:


> Hey,
> 
> Welcome.
> 
> ...





baywater said:


> hi Chris your new itinerary sounds much more doable. Ive done the Block Island and Montauk runs from Babylon at different times and my favorite format now is to cruise near the inlet the evening before leaving and sleep on the hook inside Sore Thumb or grab a berth in the State Park boat BASIN AT Robert Moses. The boat basin is rarely busy often nearly empty.
> 
> Sent from my SAMSUNG-SGH-I317 using Tapatalk





GMC said:


> Sounds like you've got a good adventure planned. It looks like your modified plan still has you doing a lot of sailing, which is what it is all about, but like an earlier post, I've been tending to put my long sails in at the beginning and end and stay/cruise in sort of a defined area. I don't know LI yet (I sail out of New Bedford), but I went to a wedding out in Sag Harbor area and it seems to me there is a good week's worth of sailing/cruising in that Gardiner's Bay, Peconic Bay, Montauk, Greenport area alone. I sail with my wife, who has limited interest in long passages. Earlier this summer, we sailed down to Newport. It took about 7 hours with the conditions. Once we got to Narragansett Bay, she was not participating in anything but hops between harbors in the bay for a week. It seems we could spend a summer in that bay and not see it all. My only point is, I've been there with the need to get out there put the miles in and see as many places as possible, but that east end of Long Island might satisfy your first long trip and not burn anyone out. By the way, almost no one ever reports back after a post like yours, so if you are inclined, let us know how it went.





captbill2209 said:


> Sounds like a great trip! very jealous, if you ever need a crew Im 26 and in the construction industry also. Live in massapequa , boat is in Napeague Harbor. Enjoy the trip and post pictures when you return.





Goodwind90 said:


> Always looking to meet new sailors and enjoy the bay! PM me and we'll set something up! Napeague is far! I've windsurfed there a few times.





SanderO said:


> 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:
> 
> ...


Hey Guys,

Just wanted to check in and thank you all again for all your help with what became an epic adventure for my girlfriend and me! Here's a summary of our trip:

We left the dock in Babylon last Saturday (8/28) evening, sailed out of the Great South Bay, and spent the night at Sore Thumb- a small anchorage just inside the inlet. We left Sore Thumb Sunday morning just after sunrise and exited Fire Island inlet with an outgoing tide in super calm conditions. The wind, as RobGallagher predicted, was out of the east at around 5 knots as we were leaving, so we motor-sailed for the first few hours until the wind shifted and picked up a bit out of the SE. We originally planned to stop for the night at Shinnecock Bay, but as we approached the inlet, the wind was too perfect to stop sailing and the forecast for the next day called for practically no wind, so we decided to sail straight through the night to Block Island. Best decision ever! We sailed under the milky way and shooting stars with a beautiful 10-12kt South breeze for the entire night until the wind completely died between MTK and Block. We motored for the final 10 NM and at around 4am we were in 130 feet of water between Montauk and Block! By first light we were approaching land and entered Block Island inlet to New Harbor just at sunrise on Monday, after 24 hours of sailing. Found a great spot in the anchorage with plenty of room even though it was the most crowded when we arrived. After cleaning up the boat and eating a nice meal, I slept like a baby for a few hours and we just relaxed on the boat for the rest of the day/night. That night, I took some long exposure shots of the stars as the boat was swaying on the hook and they came out pretty cool. The next few days we were able to explore the island a bit, make friends with a liveaboard couple who needed our help changing an anchor light on their 48' Hatteras Trawler, and just relax and enjoy the scenery on the boat. However, on the first day, it was obvious that we would need to cut the trip short and head home early due to TS Hermine approaching. The forecast for Thursday called for rain and light winds in the morning, but clear skies and steady northeast winds gusting to 15kts with east swell for the evening and through the night into Friday. So, we decided to sail straight home through the night and it was *unbelievable*!! I couldn't have asked for more favorable conditions! Fair winds and following seas!! I reefed the main and used my 130 jib for the entire ride and it was a delightful sleigh ride! I was averaging 6.5kts for a while and even hit 7kts at one point which is a record for me and my boat! The thrill of the ride kept me awake through the night, but the toughest part was the period between 3am and 5:45am (first light). Once the sun rose and warmed us up, we were greeted with schools of dolphins jumping next to and all around us! The steady offshore winds and following seas made for a fast and smooth ride home and we actually made it back to Fire Island inlet 6 hours ahead of schedule! Took us 24 hours to get to Block and only 18 hours to get home which was nice and all, but I was hesitant to enter the inlet during an outgoing tide. I was ready to just sail around and kill time for 3 hours until the tide turned, but I figured the strongest time of the current has already passed and it would only be a slight outgoing current, so I decided to motorsail in and it worked out just fine  Since we cut the trip short, we decided to spend the night at Atlantique anchorage in Fire Island near the inlet and met our friends on land for some drinks that night. At that point, the joyous feeling of accomplishment had sent in and it was just pure bliss sailing in to my home port.

It was truly an unforgettable experience and I learned so much from it. I will always be grateful for all the help and encouragement I received from you guys on this forum. As a token of my gratitude, I have posted a bunch of photos from our trip for you all to view in this Dropbox link in my next post (#11).

I can't wait to start planning our next sailing adventure and will be sure to reach out to you guys for advice again when I do!

Happy Sailing!
-Chris


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## Goodwind90 (Jul 19, 2016)

Here's the Dropbox link to my photos from the trip:

https://www.dropbox.com/sh/jhsfg0ezc9rdvkc/AACB21djn9ExgUar9nhJMWcia?dl=0


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## baywater (Sep 27, 2011)

YES!!!!!!
Chris Im thrilled to read your write up and hear you had a really fine trip! You had pretty much best case scenario ...Ive had two trips with sloppy following seas from Moriches to Montauk where the breeze coming up on reaching the lighthouse was a huge relief... Glad the Thumb worked out for you.
I lived on Block for awhile and treasure the experience. Compliments on your 28' and have a great September sailing...its the best time of all.


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## JimsCAL (May 23, 2007)

Sounds like you are hooked Chris! Welcome to the club. Block Island is one of my favorite places. Anchoring can be interesting and getting a mooring in the summer is a challenge, but it's worth the efforts. Now you can explore all those other places - Newport, Watch Hill, Martha's Vineyard, etc. on future cruises.


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## Bleemus (Oct 13, 2015)

Well done. Fine Tartan you have. Will serve you well for many adventures. Great photos. 


Sent from my iPad using Tapatalk


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## Goodwind90 (Jul 19, 2016)

baywater said:


> YES!!!!!!
> Chris Im thrilled to read your write up and hear you had a really fine trip! You had pretty much best case scenario ...Ive had two trips with sloppy following seas from Moriches to Montauk where the breeze coming up on reaching the lighthouse was a huge relief... Glad the Thumb worked out for you.
> I lived on Block for awhile and treasure the experience. Compliments on your 28' and have a great September sailing...its the best time of all.





JimsCAL said:


> Sounds like you are hooked Chris! Welcome to the club. Block Island is one of my favorite places. Anchoring can be interesting and getting a mooring in the summer is a challenge, but it's worth the efforts. Now you can explore all those other places - Newport, Watch Hill, Martha's Vineyard, etc. on future cruises.


Thank you both! I am definitely hooked and cannot wait for longer cruises in our area and even further. Thinking I'll need _at least _ 2 weeks for the next passage so I can make it to Newport. Now, the trick is to find a new career path to allow for this lifestyle! It would be great to rendezvous with you Long Island sailors one of these days!


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## CalebD (Jan 11, 2008)

Some fantastic photos in your dropbox folder Chris. You can look at the Milky Way anytime you want to now!

Sorry Hermine screwed up your plans but you did the right thing by getting off the water before she squatted here for a few days. Your mellow would have surely been harshed by the conditions we had.

It is good to build your confidence by first taking short-ish trips and you have done just that. Congratulations. Enjoy planning your next, longer trip.


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## SanderO (Jul 12, 2007)

Fabulous Chris! WOW you really push it late! The westward sail sounds like one for the memory bank... Hold on to that one!

You need to get that boat into the sound and sail in Gardiner's bay... lot's of very lovely places in Southern NE.

Chris, stunning album... thanks for sharing!


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## folicacid (Sep 12, 2016)

nice to be here.
my first sail experience was in Algeria last month, very excited.
I am really love this sport


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## GMC (Sep 14, 2009)

Nice trip and thanks for reporting. What navigation did you use?


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## Goodwind90 (Jul 19, 2016)

CalebD said:


> Some fantastic photos in your dropbox folder Chris. You can look at the Milky Way anytime you want to now!
> 
> Sorry Hermine screwed up your plans but you did the right thing by getting off the water before she squatted here for a few days. Your mellow would have surely been harshed by the conditions we had.
> 
> It is good to build your confidence by first taking short-ish trips and you have done just that. Congratulations. Enjoy planning your next, longer trip.





SanderO said:


> Fabulous Chris! WOW you really push it late! The westward sail sounds like one for the memory bank... Hold on to that one!
> 
> You need to get that boat into the sound and sail in Gardiner's bay... lot's of very lovely places in Southern NE.
> 
> Chris, stunning album... thanks for sharing!


CalebD, Thank you very much for the compliments and encouragement! I'm not too upset about the trip getting cut short because I was able to catch some of the awesome surf that Hermine left us on Long Island  I feel much more confident after this trip and will be planning the next (longer) one soon!

SanderO, Haha yeah my girlfriend and I had to plan it around her changing jobs and it worked out perfectly.

I will never forget this trip, especially the westward sail home! After a few more trips like this (much longer ones) and participating in the Clipper Race, I am hoping to have enough ocean experience to purchase a larger boat in the Mediterranean, sail it back, and possibly keep it on the North Shore (that's my rough 5-year plan). This way, I can take advantage of all the ports and harbors of New England on a regular basis.

Thank you, SanderO, for all your helpful input and advice for this trip. I will be sure to reach out to for some advice on planning my next trip!


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## Goodwind90 (Jul 19, 2016)

GMC said:


> Nice trip and thanks for reporting. What navigation did you use?


Thank you, GMC, for helping me plan it! I used a handheld Garmin 72h and plugged in all my waypoints and routes that I charted before the trip using mapsource.

The top of my upgrade list consists of an Auto Pilot system (manning the helm for several hours on end was grueling) and obviously fixed GPS system to accompany it. Do you have any recommendations?


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## SanderO (Jul 12, 2007)

Chris,
No problem! You're more than welcome to come up to NPT and do some sailing with me... Bring your partner of course or not if she's not able to. I like the plan! But I think you need to enter something like the Marion Bermuda race and get some ocean experience before attempting a delivery from the Med to NY. Looking for the right boat takes time and you can't buy without survey and sea trials and fitting out with upgrades probably. You need spares and lots of familiarity with a boat you are going to cross the pond in. I think FL is one place to find inexpensive boats. But anyplace where a couple divorces or the owner decides he's too old can be a good buy. I don't think a crossing makes sense for a shakedown cruise. ;-)


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## SanderO (Jul 12, 2007)

The PITA in sailing up and down the Sound and out east to Nantucket is the timing of the journey with the tides and wind. When they work perfectly you can make a passage rather quickly. I've hit 12 knots going thru the race! And I've see boats literally making no way sailing against the current in Plum gut. Timing is everything!


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## RobGallagher (Aug 22, 2001)

Good stuff!


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## Goodwind90 (Jul 19, 2016)

SanderO said:


> Chris,
> No problem! You're more than welcome to come up to NPT and do some sailing with me... Bring your partner of course or not if she's not able to. I like the plan! But I think you need to enter something like the Marion Bermuda race and get some ocean experience before attempting a delivery from the Med to NY. Looking for the right boat takes time and you can't buy without survey and sea trials and fitting out with upgrades probably. You need spares and lots of familiarity with a boat you are going to cross the pond in. I think FL is one place to find inexpensive boats. But anyplace where a couple divorces or the owner decides he's too old can be a good buy. I don't think a crossing makes sense for a shakedown cruise. ;-)





SanderO said:


> The PITA in sailing up and down the Sound and out east to Nantucket is the timing of the journey with the tides and wind. When they work perfectly you can make a passage rather quickly. I've hit 12 knots going thru the race! And I've see boats literally making no way sailing against the current in Plum gut. Timing is everything!


Thanks for the offer, SanderO! I would love to come out for a sail one of these days! How late do you keep your boat in the water? Would love to discuss my 'plan' and your suggestions on the boat! Yes, I was looking at the current charts in the Eldridge book and timing at The Race seems very crucial.

I'll send you a PM now.


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## JimsCAL (May 23, 2007)

Goodwind90 said:


> The top of my upgrade list consists of an Auto Pilot system (manning the helm for several hours on end was grueling) and obviously fixed GPS system to accompany it. Do you have any recommendations?


I note you have a wheel, not a tiller. A wheel mounted system (versus below decks) is you least expensive and fine for coast cruising. Most common choice is the Raymarine EV-100. 
Marine Wheel Pilot Systems


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## SanderO (Jul 12, 2007)

Chris,
I have very strong opinions about APs driven by GPS.. almost as strong as the insanity of routes for sailboats.

I am with you in how tiring helming is for hrs on end. 2 hrs in a stint can be exhausting or boring... or maybe at times thrilling. But there are 24 hrs in a day so you gotta have an AP if you sail for more than a few hrs... I am in love with my AP who is named affectionately Alison. She's been helming most of the miles sailed for 25 yrs. YIKES...never complains and doesn't have to be fed.

I have a below decks Alpha 3000. It's quite robust and has been in very stinking conditions when I would prefer not to be getting the brunt of it.

She does not take instructions from a GPS. I am the one who tells her what course to steer and I do it with a nice large dial with degrees ticked off.

I have to mechanically engage and disengage the ram. Disengaged there's no drag or impact on the helm at all.. nada.

You can adjust for yaw which quiets down the helm and she corrects less and doesn't respond to every wave for example.

I get the compass course from a GPS plotter where I can either enter the mark I need to go to... or by using the GOG line on the plotter which tells me where I would go if things remain the same. Often all I do is look at the COG line which is infinity long and turn the course dial as Alison steers until it intersects the mark I want to make. Have to verify that the course is through clear water, no rocks, shoals etc... and that's it. I check it everyone once in a while... I also have data on the plotter which tells me things like xtrack error or course to waypoint as well as course sailed

I don't bother with waypoint libraries and such... I have WAY more than enough time to set a waypoint one at a time. For example if I sail from NPT to Newport... I need to go from the R2 I think to the Green can at Sand city... to North of Eaton's Neck... That's 3 which can be done with eyeball navigation... then assuming fair winds... a waypoint at Fisher's Island another R2.... a few cans in Fisher's Island sound... don't bother with waypoints just use the course / heading lines on the plotter.... get to Watch Hill then a waypoint at PT Judith and finally Castle Hill. This is a 24 hrs sail or something with max 6 or 8 marks to make. I think I have enough time to manually set them.. Don't you? Of course once set they can be used again... or I can also follow my track which is also handy... no waypoints necessary.

I can play with trim, clean the boat, cook, eat...watch of course, check the track on the plotter, check the weather forecast... And Alison dutifully steers. What a gal! 

Essential equipment:

reliable AP
electric windlass and chain
GPS plotter with AIS and RADAR
VHF with GPS and AIS... hand held and fixed mount.
Wife

Notice in the pic the little used winch where a B&G T7plotter is mounted... it rotates and is adjacent to AP controls... I can see both real world and plotter and steer w/ Alison... there's a second windlass up down switch next to Alison. I can reach the throttle and see the engine gauges from this steering station. Display includes a flux gate compass too.

If you need help.... ask. Sailors are helpful.


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## Goodwind90 (Jul 19, 2016)

JimsCAL said:


> I note you have a wheel, not a tiller. A wheel mounted system (versus below decks) is you least expensive and fine for coast cruising. Most common choice is the Raymarine EV-100.
> Marine Wheel Pilot Systems


Thanks for the recommendation JimsCAL! I will look into this system. Seems perfect for my boat for the cruising I'll be doing with it. The only thing I need to look into is power consumption. I might need a solar panel to keep my two 12V batteries charged while the AP is in use.


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## Goodwind90 (Jul 19, 2016)

SanderO said:


> Chris,
> I have very strong opinions about APs driven by GPS.. almost as strong as the insanity of routes for sailboats.
> 
> I am with you in how tiring helming is for hrs on end. 2 hrs in a stint can be exhausting or boring... or maybe at times thrilling. But there are 24 hrs in a day so you gotta have an AP if you sail for more than a few hrs... I am in love with my AP who is named affectionately Alison. She's been helming most of the miles sailed for 25 yrs. YIKES...never complains and doesn't have to be fed.
> ...


SanderO,

You have quite the set up and I appreciate you taking the time to explain it all. Alison sounds great, but she sure is expensive! I agree with your take on APs driven by GPS- you want redundancy and minimize the chance of computer error, so I understand how manually plugging in your desired heading can be safer. I'm looking forward to getting the tour and seeing your set up in action hopefully soon! I'm curious about how you power all these gadgets.

I still have lots of research to do so I will post in the appropriate thread when I have narrowed down my options.

Thanks again for your helpful input!

-Chris


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## JimsCAL (May 23, 2007)

Goodwind90 said:


> Thanks for the recommendation JimsCAL! I will look into this system. Seems perfect for my boat for the cruising I'll be doing with it. The only thing I need to look into is power consumption. I might need a solar panel to keep my two 12V batteries charged while the AP is in use.


I have a similar (but older) autopilot on my boat. Power consumption is surprising low. Does pull a couple of amps when the drive motor turns on, but it's off MUCH more than it's running. I've never had a problem with it running down my batteries, but I mostly use it when motoring, so the alternator is keeping the batteries charged.


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## Bleemus (Oct 13, 2015)

I wish I had some photos of the AP I spent years with. Huge green box with a counter rotating knob that looked like a compass. Was built for commercial fishing trawlers and never skipped a beat. Forget the brand sadly. Makes the Alpha look futuristic. 

Sent from my Pixel C using Tapatalk


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## BarryL (Aug 21, 2003)

*Autpilot and Routes*

Hey,

I don't understand all the hate towards using routes and having the AP navigate the route. Personally, if I am going somewhere (instead of just out day sailing) I will most likely have a route set in my plotter, have the plotter running the route, and the AP steering towards the waypoints. This assumes that I can sail towards the waypoints. If not, I will still try to follow the route, but taking may take me far off the route.

I have my routes preloaded for a number of reasons:
-I like to look at paper charts and ensure that the route I want to take is safe and makes sense
-If the destination of far away (say 30+ miles) I will have alternate destinations listed in case the weather goes downhill
-I am on the only one on the boat who can sail, read a chart, etc.
-When the plotter is running the route I can see at a glance how far it is to the next waypoint, how long it will take to the next waypoint, how far to the destination, how long to the destination, etc. This enables me to make good decisions like perhaps I need to go faster (motorsail?) in order to make it to my destination before dark, before the current turns, before I run out of water at low tide, etc.
-I don't like surprises. Having the route set ahead of time means I can spend more time thinking about what beverage to have at the destination, what restaurant to eat dinner at, or how to fix whatever has broken during the trip.

Having the AP follow a route is little different from aiming the boat at a waypoint, and engaging the AP. The benefit is that the route allows the AP to compensate for changes in current, wind, etc. When the AP reaches a waypoint it beeps and I must press a button before it goes to the next waypoint.

All in all there are lots of way to operate your boat and you can decide what works best for you.

Barry


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