The Long Island Loop – Points of Interest

Discussion in 'Sea Ray Lifestyle & Cruising' started by Alex F, Dec 21, 2009.

  1. Alex F

    Alex F Well-Known Member

    Nov 14, 2006
    East Coast
    2005 420DB with AB 11 DLX Tender, Raymarine Dual E120 MFD/Radar/XMWeather, ST7001 A/P, AIS, SeaLift
    T-Cummins 450Cs Straight-Drives, 9KW Onan Generator, 40HP Yamaha for tender.
    One of the trips I always wanted to do is explore beautiful LI, NY shores. Since I’d like to explore both sides of the island (south and north shores) I’ll call it “The Long Island Loop”. Coming from Jersey shore I’m thinking that it most logical to explore south shores first (traveling from west to east after reaching the LI south shore), then make my way over to the north side of the island, via Shinnecock Canal, and continue my way from east to west on the LI sound side. At this time I think that making total of 4 stops, spending about 1.5 days at each stop, and completing the trip in about a week or so would look like comfortable itinerary. As the first stop I’m looking at Fire Island, which from what I hear is pretty inviting place. Thus, I need to choose another 3 (1 on south shore and 2 on north shore) interesting stops to complete my LI loop.

    I know we have good number of members from LI area. I would appreciate any suggestion regarding what towns and marinas to pick for my subsequent stops. If you could also suggest some details on things to do on shore and navigation tips that would be great.

    Thanks,
    Alex.

    If anyone wants to skip reading through all of the posts in regards to planning, you might just want to read my write-up on the trip here (page #12) http://clubsearay.com/forum/showthread.php?t=26021&page=12
     
    Last edited: Sep 18, 2010
  2. Lazy Daze

    Lazy Daze Well-Known Member TECHNICAL Contributor

    Apr 21, 2009
    PA
    Various
    Various
    I'm not from LI, but I've found Port Jefferson to be very cool. Nice shops to walk around and visit (a little on the pricey side, which is why I say "visit" :smt001).

    The "break-water" at the entrance to the harbor has a nice sandy shore on the harbor side. You'll often see many boats anchored there for lunch.

    On edit: I should mention that I haven't been there in a number of years, though.
     
    Last edited: Dec 21, 2009
  3. Rich

    Rich New Member

    96
    Jan 5, 2008
    Jericho, NY
    270 Amberjack 2005, Raymarine C70, Fishing Package
    350 Mercruiser w/ Bravo III Drives
    I agree with Port Jefferson, but before, I would stop at Greenport, which has a handful of nice marinas. Afterwards you go through Plum Gut and head west. A stop in Stamford CT for lunch - Crab Shack - worth the visit !! have a great time.

    Rich
     
  4. Lazy Daze

    Lazy Daze Well-Known Member TECHNICAL Contributor

    Apr 21, 2009
    PA
    Various
    Various
    I forgot about that place! :thumbsup: Bringing back some good memories!
     
  5. Alex F

    Alex F Well-Known Member

    Nov 14, 2006
    East Coast
    2005 420DB with AB 11 DLX Tender, Raymarine Dual E120 MFD/Radar/XMWeather, ST7001 A/P, AIS, SeaLift
    T-Cummins 450Cs Straight-Drives, 9KW Onan Generator, 40HP Yamaha for tender.
    Rich,
    I don't want to get my crew tired from running around, so I was thinking to leave CT as a trip of its own. I'm sure it has tons of cool places.

    Greenport looks like a nice place. Do you have some detailed tips on Greenport?
     
  6. Alex F

    Alex F Well-Known Member

    Nov 14, 2006
    East Coast
    2005 420DB with AB 11 DLX Tender, Raymarine Dual E120 MFD/Radar/XMWeather, ST7001 A/P, AIS, SeaLift
    T-Cummins 450Cs Straight-Drives, 9KW Onan Generator, 40HP Yamaha for tender.
    Port Jeff, could be one of the stops heading home. I need to look in to it in more details.
     
  7. gnealon

    gnealon New Member

    570
    Apr 8, 2009
    West Babylon, NY
    2005 280 DA, Garmin 4208
    "Ship Faced"
    Twin 5.0L Merc BIII
    Alex - I did a trip from Lindenhurst LI to Greenport over the summer. Beautiful trip!!! We stayed at Mitchell park marina. Its a really nice Marina and very close to the town... included Claudio's (famous seaford restaurant). If you are going w/ kids... they have an antique carousel there which is pretty cool.

    Have fun and be careful! If you venture into the Great South Bay make sure your maps/gps is updated. Its very shallow and many passages are narrow. :wow:
     
  8. katricol

    katricol Active Member SILVER Sponsor

    Mar 4, 2008
    LONG ISLAND SOUND
    2000 540DA
    CAT 3196 660 HP
    Alex..many great sites on L I . Montauk (the end) would be a must see. Sag Harbor, definately ! Shelter Island has numerous anchorages that are gorgeous for a lunch or overnight. Don't worry about great peconic bay , a good gps will make it easy. Agree about Greenport and Mitchell's, and also Port Jeff. My charts are on boat, but if you like to anchor-up pm me . Ric
     
  9. bmac

    bmac Active Member

    Jan 11, 2008
    Holbrook, NY
    2006 58 Sedan Bridge, Walker Bay Generation 390 RIB w/40hp Yamaha, 2014 Wellcraft 232 CC w/Yamaha
    MAN 900 CRM
    Alex

    That's a lot of helm time over the course of a week, especially if you plan on spending a day and a half in each port. Nonetheless, it can be done IF the weather cooperates and your comfortable being in the Ocean and the LI Sound (which can seem like the Ocean). I would suggest from NJ your first stop being Freeport, then on to Westhampton Beach through FI Inlet, Great South Bay and Moriches Bay. I'd then go on to the Shinnecock Locks out into the Peconic and out to Greenport. I prefer Townsend Manor Marina to the Town Dock, (no gawkers, has a pool and is still a short walk to town). I'd then continue on to Port Jefferson and stay at Danford's Inn and Marina. This is where it gets tough for you. From PJ you'd have a long day of travel home through the Sound and East River. I'd give some thought to staying over the last night at Chelsea Piers in Manhattan (can be rough as it's not protected) or my preference, Liberty Landing in NJ. Good luck in your planning and don't hesitate to ask any questions.
     
    Last edited: Dec 21, 2009
  10. Larry

    Larry Active Member

    Oct 19, 2006
    Oakland, NJ
    2004 42 Sundancer
    Hydraulic platform
    Cockpit air
    KVH M3
    450hp Cummins
    I totally agree with everyhthing that Ric and Brian said above. It is a tough call, there are allot of great places Montauk, Greenport, Sag Harbor, and Port Jeff should all make it to your short list. I agree running from Port Jeff home (no other have to ports on the North Shore heading West) would not be practical and that you should have stop over, I would go to Liberty Landing just because of the rocking at Chelsea.
     
  11. Rocket

    Rocket Member GOLD Sponsor

    555
    Jan 14, 2008
    Long Island NY
    2007 48 Sundancer
    Previous: 2004 420DA, 2007 320DA, 2006 240DA
    Cummins QSC 540 8.3
    Alex - I agree with BMAC, trip around LI would be at least 10 days. Head in the FI inlet, if you have kids and it is a weekday stay at Atlantique. It is a great place about 1/2 hour from the inlet which you have a bay side beach or can walk over to the ocean. No town but private if you like to camp out. If you need some action from there, you can dink over to ocean beach, lots of restaurants and shops. I recommend you stay on the inside go east throught the great south bay, through moriches bay, and Westhampton town dock is a definite. (2 hour ride from FI to Westhampton) If you head through moriches, you need to plan with High tide through a certain area. A great little town, 1 night stay over is fine.I would head east on the inside to Tiana bay and up through the Shinnecock canal, up to Greenport. Some nice places to stay with pools. Do not miss Montauk, i would stay at the yacht club for a few days. From there you can head back on the ocean and skip the north shore or if you choose the north shore will probably need another stop before you reach home.
     
  12. Alex F

    Alex F Well-Known Member

    Nov 14, 2006
    East Coast
    2005 420DB with AB 11 DLX Tender, Raymarine Dual E120 MFD/Radar/XMWeather, ST7001 A/P, AIS, SeaLift
    T-Cummins 450Cs Straight-Drives, 9KW Onan Generator, 40HP Yamaha for tender.
    Guys, this is great info you're giving me. Some of you are also confirming what I kind of anticipated that it's not possible to cover the island in one trip. Based on your suggestions, it looks like most of the cool stops are on the south shore, aside from Greenport and Port Jeff. I'm sure I'll have to comeback on another trip to cover those stops that I'll miss the first time. BTW, this trip is also in a way to prep admiral going to Black Island some day (may be the following season).

    I'll be travelling with kids so this is why I would like to spend more time exploring the shore and towns vs. travelling between the stops. That's why I thought spending approx. 1.5 days at each stop could be a good approach. Meaning, once I get to the island and start hopping between the ports, if I could be in a port by 12-1pm, then I can spend remaining day and next full day.

    So far looks like the following are making the preliminary must see list of stops:

    Fire Island or Freeport
    West Hamptons area
    Greenport
    Sag Harbor
    Montauk
    Shelter Island

    I do realize that 6 stops are overwelming even if I streach the trip to include both weekends (total of 9 days). I'
    m also taking off the PJ, b/c it looks like a lot of travelling just for a single stop.

    BTW, besides visiting nice towns I'd love to explore some whild and may be spend overnight on anchor in place like Shelter Harbor.

    Any thoughts on best way to narrow down the list considering the fact that most likelly I'll be making my way back via south shore?
     
    Last edited: Dec 22, 2009
  13. bmac

    bmac Active Member

    Jan 11, 2008
    Holbrook, NY
    2006 58 Sedan Bridge, Walker Bay Generation 390 RIB w/40hp Yamaha, 2014 Wellcraft 232 CC w/Yamaha
    MAN 900 CRM
    Well Alex, to help you along, are you interested in visiting towns to walk around with great restaurants (Freeport, Westhampton Beach, Greenport), places with a beach (Fire Island), traditional historic boating, fishing and yachting ports (Greenport, Montauk, Sag Harbor) or just a place to relax (Shelter Island, btw that's where the picture on here is from). Oh, and once you get to Montauk, Block Island is less than 45 minutes away, usually a pretty easy trip. I'd try and stick to 4 ports in 9 days. We usually do 4 in 15 and always feel hurried to relax.

     
  14. JohnEGraham

    JohnEGraham Member

    907
    Aug 5, 2008
    Long Island, NY.
    250 Sundancer 1998 5.7.
    350 Merc / Bravo 3
    Hey, As far as the list, one problem is going through Moriches inlet ( if you go that way) you have to figure in the tides. ( plenty of info on this site, but a couple of hours around high tide is needed)
    so you have:
    Fire Island ( beach area, resturant ) or Freeport No Beach but Food
    West Hamptons. Most use West Hampton beach to be able to time the tides though Moriches
    Greenport A Must! Townsed+
    Sag Harbor ( big money)
    Montauk + Everything there
    Shelter Island (Quite )
    So I would vote for Skip Freeport & Shelter Island for an active family with kids.
    I would hit Fire Island on the way back.
    Hey, With 20 Plus inches of snow on the ground here its nice to think about all of this. :)
     
  15. Larry

    Larry Active Member

    Oct 19, 2006
    Oakland, NJ
    2004 42 Sundancer
    Hydraulic platform
    Cockpit air
    KVH M3
    450hp Cummins
    I think it maybe a wise call to omit Port Jeff this trip (still worth going but maybe if you are doing the CT coast it will make sense to hop over). All the other places you have listed are great destinations in themselves, obviously if you can elongate your trip while up in the area do so, and try to hit Block, it is only a short hop over from Montauk and you will not regret it.
     
  16. Lazy Daze

    Lazy Daze Well-Known Member TECHNICAL Contributor

    Apr 21, 2009
    PA
    Various
    Various
    Have you looked at any of the town's websites? Sometimes they're informative, sometimes not. There's usually a contact phone number on there to call someone - tell them exactly what you're planning and ask for their thoughts on where to go / what to do in their town. Let them sell you on their town! :smt001
     
  17. rcknecht

    rcknecht Active Member

    Mar 23, 2009
    toms river,nj
    340 Sundancer 2001
    T 454 MPI
    Alex,

    We did the "loop" with our 300 in 2001. Our first stop was to meet a friend at his Marina in Edgewater NJ. Then we went under the GW and through the Spuyten Duyvil swing bridge up the Harlem River, through Hells Gate and anchored at Port Jeff. From Port Jeff we went up the CT River to Essex. We stayed at the Essex Inland Marina. Essex was a great place. Then we went through the Plumb Gut and stayed in Green Point, Silver something marina... We planned on anchoring by Shelter Island, but it rained for three days. We did not do much on the South, just went through the Shinacock cannel and inlet and headed for the Manasquan Inlet. You might want to take a short run to Block Island if you make it to the end of LI it is not that far, and I here it is a great trip... Port Jeff was a great anchoring spot.

    Bottom line is, I think the Sound (North side of the Island) is more fun since it is deep, protected, and has interesting ports of call...
     
  18. jg300da

    jg300da New Member

    Oct 9, 2006
    None
    Your
    Business
    Alex,

    Since you are entering through the Shinnecock Canal, Sag Harbor is a must and of course Greenpoint and Shelter Island. Then it's just a right turn in Gardiners Bay and halfhour to Montauk, our favorite. Heading west along the north shore from Plum Gut it's pretty vacant until you reach Port Jefferson, also a must see. From there it's about 1 1/2 hrs west to Huntington/Northport with plenty of shopping and great places to eat. Further west it's Cold Spring Harbor, Hempstead Harbor and Port Washington, the last two have excellent Brewers Marina facilities.
     
  19. bmac

    bmac Active Member

    Jan 11, 2008
    Holbrook, NY
    2006 58 Sedan Bridge, Walker Bay Generation 390 RIB w/40hp Yamaha, 2014 Wellcraft 232 CC w/Yamaha
    MAN 900 CRM
    Although a lot of people will transit it, Moriches Inlet is considered to be non-navigable. My insurance policy specifically excludes coverage for that Inlet. Moriches Bay is also a difficult transit and must be done close to or at high tide at the Moriches USCG Station. One note is that the Bay is supposed to be dredged this winter which should help the navgating that needs to be done through this stretch. Fire Island Inlet is no prize lately either but is still navigable as the USCG does a good job of moving markers when necessary. If I were you I'd consider the following:

    Home to Watch Hill (a federal marina on Fire Island)
    Watch Hill to Greenport (Townsend Manor) (3hrs.)
    Greenport to Block Island (Champlins or Boat Basin) (1 1/2 hrs.)
    Block Island to Montauk (Montauk Yacht Club) (45 mins)
    Montauk to home.
    I think the big issue for you will be fuel on the way home. Unless you leave from Montauk and go back through the Shinnecock Canal there's really nowhere to stop for fuel unless you duck in at Jones Inlet. You might therefore want to add a night at Westhampton Beach on the way back.

     
  20. Alex F

    Alex F Well-Known Member

    Nov 14, 2006
    East Coast
    2005 420DB with AB 11 DLX Tender, Raymarine Dual E120 MFD/Radar/XMWeather, ST7001 A/P, AIS, SeaLift
    T-Cummins 450Cs Straight-Drives, 9KW Onan Generator, 40HP Yamaha for tender.
    This is the best way to "survive" the winter season :grin:. I always try to plan my trips during winter, so come spring my mind is more in to technical items to get the boat ready and finish other planned boat projects.

    Absolutelly, I always search the web to find as much as I can. BTW, calling up the township to ask more details on activities is a good idea. But, as you know, that the best source of information is from people who've been there. I'm positive that some of the details I'm getting here from board members is not written in any cruising guide.
     
    Last edited: Dec 23, 2009

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