South Shore
The 5 ft. draft would be the biggest problem, but still OK. I came from a 38' sailboat with a draft of 4'2" and some of my friends draw 5'. You could still transit the Sh. Canal, you would have to time your trip west with a high tide at Moriches Inlet. It gets real skinny over that way. The good thing is the bottom is soft sand. At high tide, if you bump, just power right thru. (I can say that from experience).
I have a 27' Ranger Tug. I down sized for a few reasons. I love the boat, had to get used to the limited space.
I see someone mentioned the Connitiquot River. That is one of my favorite hang out spots. I anchor out, usually rafting up with other boats. No need to get a slip. The Snapper has ice, fuel and you can dink in for dinner or a drink.
I also love Fire Island. The slips are mostly owned by towns. There are 2 federal beaches. Watch Hill, across from Patchogue. The slips are 1st class and it's a short walk to the ocean beaches. Sailors Havon is another one, west of Watch Hill. It is across from the Islip or Bayshore areas. There are water taxis on the Fire Island side. You can go from beach to beach. If you like to walk, the boardwalk does the whole thing. There are grocery stores, resturants, bars, all the necessities. There are no cars, so it's very nice. Only the cops and fire dept have cars. Also very few permanent residents have cars. For the most part, you will see more deer then you do cars. Each beach has it's own "theme". There are family beaches, party beaches, gay beaches, RICH gay beaches, nude beaches, regular beaches, it's all good on Fire Island. All you need is a cooler full of beer and some sun block and your all set. I'm not sure of the town owned marina's. Some have different rates for transients, some don't allow transient's, some only allow transients during the week. You would have to go online and check them out. I will be making the trip from Greenport (a great place) to Connetiquot River in August. If the timing is right we can meet up and I can go over the charts with you.
chester613@outlook.com
The South Shore is very nice, so is the North Shore. The difference is the depth of the water. The North Shore see's 60', even 100'. The South Shore, you better be in the channel. 6 - 8 ft is normal. There is 20 ft. in the State Channel, that's probably the deepest part. Also the bottom on the North Shore is rocks, the South Shore is soft sand.
Where would you be coming from? New York Harbor is a trip worth making as well. City Island, Manhasset Bay, Port Jefferson, all very nice. You could also go south around Long Island and end up in Sheepshead Bay Brooklyn. Grab a mooring and have some of the best Italian Food in NYC. I would volunteer to help you plan your trip. Let me know where you are starting, how much time you have and what type of activities you enjoy.
Then you could do the same for me. We love exploring new places. In 2017, we are retiring, so we will have a bunch of time on our hands.
