The Long Island Loop – Points of Interest

I had an opportunity to share this thread with admiral. We were able to iron couple of things out that in the way helps to continue planning. She made a good point that for this trip we should limit to no more than a week due to the fact that this is not like every stop would have amusement parks, so the last thing we want is for the kids to get bored. I’ll try to have the ports of call with mixed activities. The other point admiral made is that she’d like to go to Black Island on the separate trip. I think this is fine, b/c when we’ll be back we can hit other ports.

Brian,
Your last suggestion for ports looks interesting and gave me an idea to make bigger jumps between the ports to cover those that are on must visit list. So, I’m thinking that something like this can work (I got some rough distance numbers from my PC planner):

NJ to Westhampton (~85-90nm)
Westhampton to Greenport (~25nm), stopping at Shelter Island for lunch.
Greenport to Montauk (~20nm)
Montauk to Fire Island (~55nm)
Fire Island to NJ (~60nm)

I was thinking that it might be easier to have longer run on the first day of the trip, that’s why I’m thinking to do Westhampton as first stop. If I make the WH as the last stop, then the longest trip would be on the way back home, which I’m not sure is the best approach.

What you guys think, is this a good rough plan? How long would you say it’s better to stay a particular port? If I recall, I’ve read that some marinas require 2 nights minimum stay (I think it was Townsend Manor Marina in Greenport). Would you think that I need to spend 2 nights there? I don’t know these towns too well, but from what I recall the only port that might be worth staying for two nights is the Montauk.
 
Sag Harbor is only a short ride (less than 1 hour) from either Montauk or Greenport. I would stay only one night and get to see Sag.
 
Hey, I like it.
NJ to Westhampton (~85-90nm)
Westhampton to Greenport (~25nm), stopping at Shelter Island for lunch.

Greenport to Montauk (~20nm)
Montauk to Fire Island (~55nm)
Fire Island to NJ (~60nm)

Re: Greenport for 2 days is fine for Kids. Lots of them. They have a great pool. They also have activities for the kids. They have a Painting activity when I was there and saw lots of kids / adults involved for a couple of hours, I don't have young kids ( 18, 19 now) so I don't know what other thing they have but they are worth a call.
The Main town has a new (old ) Merri-go-round. A Working Black-Smith where you watch them make items the old fasion way. The Townsend is at the end of the Canal so its real calm. Lots of Big - Big boats. We have a 25ft Sundancer and we where the 2nd smallest and felt like I was sleeping in my own bed. Bring you Dingy, if you have one, they have a seprate dock with plenty of thing to see.
 
Sag Harbor is only a short ride (less than 1 hour) from either Montauk or Greenport. I would stay only one night and get to see Sag.

Ric,
I see your point. However, as Brian had mentioned earlier, I have to avoid a situation when we hop from port to port and don't give ourselves chance to relux just a bit. So, I have to find the "golden middle" and find a port to stay two days. Despite the fact that I woul love to visit more ports I don't think I can add any more to my itinerary.

I'm pretty sure that thanks to this thread I'll be able to have a rough plan for the following year when I'll be able to add Block, Sag and other ports you guys have suggested.
 
Hey, I like it.
NJ to Westhampton (~85-90nm)
Westhampton to Greenport (~25nm), stopping at Shelter Island for lunch.
Greenport to Montauk (~20nm)
Montauk to Fire Island (~55nm)
Fire Island to NJ (~60nm)

Re: Greenport for 2 days is fine for Kids. Lots of them. They have a great pool. They also have activities for the kids. They have a Painting activity when I was there and saw lots of kids / adults involved for a couple of hours, I don't have young kids ( 18, 19 now) so I don't know what other thing they have but they are worth a call.
The Main town has a new (old ) Merri-go-round. A Working Black-Smith where you watch them make items the old fasion way. The Townsend is at the end of the Canal so its real calm. Lots of Big - Big boats. We have a 25ft Sundancer and we where the 2nd smallest and felt like I was sleeping in my own bed. Bring you Dingy, if you have one, they have a seprate dock with plenty of thing to see.

John,
Thanks for some details on Greenport. I have 5yr old (“little bunny energizer” who doesn’t sit still) and 12yr old girl. I’m sure they’ll be happy to participate in those activities that you had described. I do have a dingy with 4hp Tohatsu motor, which I’d love to use to explore places ones I get to a port.

Hey, believe me I know the feeling about being smallest boat. Every time we visited FT. Lauderdale the feeling remained whether we were in 175BR or 240DA.

Can you guys share some details on things to do in Montauk?
 
Skip the stop at Shelter Island for lunch. You could throw a rock from Shelter Island and hit Greenport, so why the extra hassle of tying up and casting off again? Besides, there are great places to lunch in Greenport. As for Townsend Marina, two days is plenty. The pool is great, very clean, and the on site restaurant is very nice and convenient. An added bonus is that you don't have to leave your slip to gas up. The gas lines reach all the slips which saves a lot of time as you fuel up for the next leg of your trip.
 
Skip the stop at Shelter Island for lunch. You could throw a rock from Shelter Island and hit Greenport, so why the extra hassle of tying up and casting off again?

I was thinking that in order to avoid tying up twice to do the stop on the way to Greenport. If we'll be staying 2 nights in Greenport, then it plays nicelly and I can spend little extra time in Shelter Isl and then finally get to Greenport.
 
NJ to Westhampton (~85-90nm)
Westhampton to Greenport (~25nm), stopping at Shelter Island for lunch.
Greenport to Montauk (~20nm)
Montauk to Fire Island (~55nm)
Fire Island to NJ (~60nm)

I was thinking that it might be easier to have longer run on the first day of the trip, that’s why I’m thinking to do Westhampton as first stop. If I make the WH as the last stop, then the longest trip would be on the way back home, which I’m not sure is the best approach.....

Alex

You're getting there and I think it works as you've laid it out. One, amongst many, consideration you might want to make is transiting Moriches Bay. You'll want to enter the bay 20 minutes after high tide at the USCG station. Westhampton Beach is just east of Moriches so as you have it laid out you'll need to time your arrival at the back end of a 90nm trip. No matter how far I travel by boat, that short transit through Moriches Bay is the one I dislike the most (it is supposed to be dredged next month). It might be a better idea to do Fire Island first and face Moriches at the end of your first hour of your next leg and then do Westhampton Beach as your last stop before heading home. That way you'll have Moriches done in your first 15 minutes of your last leg, can stop for fuel in the Great South Bay before heading out into the OCean for home through Fire Island inlet. Just a thought. (BTW, can you tell how much I hate Moriches Bay? This will raise some eyebrows, but when I go through the Mroiches I do NOT come off plane and I DO keep my eyes peeled to the bouys with the admiral watching for the inevitable fishing boat in the channel, but that's for another thread). This reminds me, I need to start planning my trip to Newport, Marthas Vineyard and Nantucket for last week of July and first week of August....
 
I think you have a pretty good idea what to do in Greenport. In Montauk, I would suggest staying at the Montauk Yacht Club. They have kid activities, a great pool, nice spa, good restaurants and a great waterfront bar. They also have a shuttle that takes you into town, which is your typical seaside town with the requisite shops and pizza places. Things to see and do; Montauk Lighthouse (commissioned by George Washington), Deep Hollow Ranch (oldest cattle ranch in the U.S.) great place to take the kids for beachfront horseback riding, Gossmans Dock, some shopping, fishing fleet, GREAT restaurant and ice cream place for the kids to end the day, golf at Montauk Downs (if you can get away with it and are so inclined), Star Island YC, home port of Frank Mundus of Jaws fame. You could spend your entire day at MYC around the pool, never leave and be content with the kids or do any or all of the above.
 
My wife just yelled at me asking what the hell I've been doing all morning. I think I need to run down to the boat....I mean supermarket right now....
 
Alex

You're getting there and I think it works as you've laid it out. One, amongst many, consideration you might want to make is transiting Moriches Bay. You'll want to enter the bay 20 minutes after high tide at the USCG station. Westhampton Beach is just east of Moriches so as you have it laid out you'll need to time your arrival at the back end of a 90nm trip. No matter how far I travel by boat, that short transit through Moriches Bay is the one I dislike the most (it is supposed to be dredged next month). It might be a better idea to do Fire Island first and face Moriches at the end of your first hour of your next leg and then do Westhampton Beach as your last stop before heading home. That way you'll have Moriches done in your first 15 minutes of your last leg, can stop for fuel in the Great South Bay before heading out into the OCean for home through Fire Island inlet....

Thanks for pointing out this troubled area. I'll be checking the tide schedule and see if how this fits better.

I think you have a pretty good idea what to do in Greenport. In Montauk, I would suggest staying at the Montauk Yacht Club. They have kid activities, a great pool, nice spa, good restaurants and a great waterfront bar. They also have a shuttle that takes you into town, which is your typical seaside town with the requisite shops and pizza places. Things to see and do; Montauk Lighthouse (commissioned by George Washington), Deep Hollow Ranch (oldest cattle ranch in the U.S.) great place to take the kids for beachfront horseback riding, Gossmans Dock, some shopping, fishing fleet, GREAT restaurant and ice cream place for the kids to end the day, golf at Montauk Downs (if you can get away with it and are so inclined), Star Island YC, home port of Frank Mundus of Jaws fame. You could spend your entire day at MYC around the pool, never leave and be content with the kids or do any or all of the above.

This is great info, do you have any recommendations for Shelter Island (what's the better spot to anchor, I'm sure there're number of spots)?

Any suggestions on things to do in Westhampton?
 
Last edited:
This is great info, do you have any recommendations for Shelter Island (what's the better spot to anchor, I'm sure there're number of spots)?

Any suggestions on things to do in Westhampton?

Two primary protected harbors for Shelter Island....Coecles Harbor and Dering Harbor. From Dering you can easily dinghy into town. If only anchoring I would suggest Coecles. Both are really short hops into Greenport, so if headed for Greenport I'd suggest lunch at anchor in Sag Harbor instead.

Westhampton Beach you have two alternatives for marinas. The more expensive of the two is the Westhampton Bath and Tennis Hotel and Marina. Very nice facilities on the ICW with its own Ocean front beach. Short cab ride or long walk into town. The Westhampton Beach Town marina is also very nice, but no facilities other than bathrooms with showers, however it's only a 2 block walk into town. Not much to do in town except eat and watch the Hamptonites get parking tickets. A couple of nice restaurants, a great bakery, a movie and the requisite high end stores and ice cream shops. For adults I always recommend the town marina but with kids I'd suggest the Bath and Tennis Club.
 
so if headed for Greenport I'd suggest lunch at anchor in Sag Harbor instead....

Brian,
What part of Sag Harbor you think is worth visiting instead of Shelter Island?
 
Brian,
What part of Sag Harbor you think is worth visiting instead of Shelter Island?

If you're just anchoring for lunch I'd do Coecles Harbor in Shelter Island (I know I just corrected myself). It's more protected than the anchorages just outside the Sag Harbor breakwater. If you're looking to dinghy in then I'd suggest Sag Harbor and one of the mooring fields just inside the breakwater. The village in Sag Harbor is small but quaint though I'm not sure either it or Shelter Island are worth the hassle of a dinghy ride for a short visit. Either place on land lunch will be $$$$.
 
My plan was to stop by Shelter Island (as it was on the list as one of the must visit places) making it midway stop on the trip from Westhampton to Greenport. If all goes well this could be nice lunch, swim and engoy the beach couple of hours stop before we get tied up in the slip at Greenport. Since we'll be staying there for two nights, depending on the type of activities that will be offered during our stay we may consider taking the boat to SH for exploring the area and be able to swim during the day hours. I'm thinking that this could be plan B if kids get bored at GP.

BTW, I found the website http://www.bathandtennis.com/marina.html for Westhampton Bath and Tennis Hotel and Marina, the facility looks awsome. Do you recall by any chance what they charge per foot (I couldn't find the rate anywhere)?
 
Last edited:
My plan was to stop by Shelter Island (as it was on the list as one of the must visit places) making it midway stop on the trip from Westhampton to Greenport. If all goes well this could be nice lunch, swim and engoy the beach couple of hours stop before we get tied up in the slip at Greenport. Since we'll be staying there for two nights, depending on the type of activities that will be offered during our stay we may consider taking the boat to SH for exploring the area and be able to swim during the day hours. I'm thinking that this could be plan B if kids get bored at GP.

BTW, I found the website http://www.bathandtennis.com/marina.html for Westhampton Bath and Tennis Hotel and Marina, the facility looks awsome. Do you recall by any chance what they charge per foot (I couldn't find the rate anywhere)?

Last time I was there was a holiday weekend. I think the rate was either $4.50 or 5.00/ft. plus $30 per night electric.
 
I had some time to get back to my research for the trip and while looking for some info for Fire Island (first the place to stop by for lunch after we cross from NJ and then to spend a day or two on the way back home) I found interesting and very informative site http://www.loving-long-island.com/fire-island.html and http://www.loving-long-island.com/ocean-beach.html, at the bottom of the page there're few more good links.

Based on my preliminary findings I see marina few marinas I could use as a lunch stop:
-Flynn's
-Fire Island Pines
-Atlantique

Does anyone have experience in these places, are these good choices for a lunch stop?

It looks like that Atlantique might be tough to get to due to residents policy restriction.
 
Last edited:
We stayed at Flynn's one night last summer, It was ok. We got there late and only went there as a last resort.

Not sure how much there was for kids there, it seemed to be more of a club/bar. But if you're just thinking for lunch, it may be fine.

I wanted to check out Sailors Haven and the Sunken Forest while in the area, but ran out of time. Here's a link:
http://www.nps.gov/fiis/planyourvisit/sailorshaven.htm


I forget what we paid to dock at Flynn's but we were given $100 back in coupons for drinks at the bar.
 
Last edited:
Flynn's is great for lunch and it's a short walk to the beach which is great. It's first come though, they don't take reservations. Also their marina is very tight and they have dockhands that jump right on to the bow of your boat to guide you into the tight slips. Kinda strange the first time you experience it. Also not a good overnight place if you have kids. They party till 4am and the shuttle/ferry constantly picks up and drops off right from their docks. Very noisy.
 
Alex If you are looking for a place for a quick lunch and then head back out east you can hit Nickys over in Bayshore it is across the bay but you can fuel up and do pumpouts if you want and the food is good but not much else to do there. I dont know what inlet you plan on coming in but if you come in Fire Island inlet which looks to be about 80 miles from barneget Light inlet. Either way you kind of have to head to the north side of the bay either by Kismet which also has lunch or by Ocean bay Park where flynns is. There is a lot of places to eat between kismet and Ocean bay park.There is no place by fire island to fuel up all gas docks are on the mainland Bayshore, Oakdale, Patchogue and more out east I just dont fuel up out there. Rich
 

Forum statistics

Threads
112,950
Messages
1,422,865
Members
60,932
Latest member
juliediane
Back
Top