Bridge
Coming in the Fire Island Inlet, you will clear the single span 65' Robert Moses fixed bridge. Continuing east and hugging the inner shoreline of Fire Island, there is plenty of water for you in the East Channel. Anchor off Atlantique or Ocean Beach, or like Bob says, hit Sailor's Haven or Watch Hill. The West Channel will take you straight up to the vicinity of the Bay Shore Marina off of R #2, with fuel, pump out, and restaurants. Also plenty of water in the North Channel, but stay east of the double span Robert Moses Causeway - it has a reported clearance of 60', and the water gets shallow on the west side of that bridge. An up to date chart and/or chartplotter is a must, as is a reliable depth finder. But the Great South Bay is a nice place to spend a few days.When you're ready to continue to Block, you will have to go back out the Fire Island Inlet to the Atlantic and head east. Do not attempt to enter the Moriches Inlet. I would use caution at the Shinnecock Inlet - I have heard that sailboats will duck in there for a night on the way out to Block, but I don't have any knowledge of it, and it does get shallow in there.If you have time on the way to/from Block, Benny is right about Greenport, Sag Harbor, Pt Jefferson, Montauk, and Northport. To that, I would add Mattituck, Huntington, Oyster Bay, and Norwalk. And of course, coming down the East River through the city is unbelievable. Just make sure you read the tide charts and go with the flow, otherwise you will be fighting up to a 5.5 kt current. Have fun....