I prefer to fly the Skyline route in the Bravo because ATC will almost always approve a West to East transition across Manhattan over Central Park to the East River. Then a right turn southbound along the East River back to the Battery (southern tip of Manhattan). In additional to the sights along the Hudson, you get to see Central Park South, The Museum of Natural History, The Museum of Modern Art, and the Guggenheim Museum on the leg across Central Park. And the East Side sights down the East River (59th Street Bridge, Cable crossing to Roosevelt Island, The UN Building, Manhattan Bridge, Brooklyn Bridge, South Street Seaport, and the Staten Island Ferry terminals.
You'll need to be talking to ATC and get Bravo clearance. Tell ATC that you want to do a Manhattan tour with a Central Park transition to the East River, followed by your choice of a circuit or two around the Statue of Liberty, or a continuation northbound up the Hudson. Start at the Verrazano Narrows Bridge and fly north up NY Harbor aiming for the East side of the Hudson River. You will get handed off to LaGuardia Tower near the Freedom Tower and they will be the ones to give you the Central Park transition clearance. You can't miss Central Park in the middle of Manhattan (a giant rectangle of green). When you get about half way up Central Park turn right 90 degrees. When you reach the East River make another right 90 and fly down the East River. At the bottom of Manhattan you can either fly straight ahead to the Statue of Liberty and circle there, or turn right back north up the Hudson to the George Washington Bridge to see the sights of upper Manhattan. If you fly to the GWB before you circle the Statue of Liberty, get approval to make a 180 and head back downriver until you reach the Statue where you can do a few circuits. Finish by flying back south to the Verrazano Narrows Bridge and west out of the Bravo.
This route keeps Manhattan on the right side of the plane and gives a great view to passengers. You're going to be busy flying the plane and looking out for traffic call-outs anyway.
I choose to limit my Manhattan flights to warm weather. If the engine quits you are almost certainly going to have to ditch because there is nowhere safe to put it down on land.
A night flight has its own special attraction. It isn't as easy to see some of the smaller landmarks as it is in daylight, but the overview of the lights is spectacular. If you're going to be in the area for a full day, you might want to try it both day and night.
Whatever you decide, enjoy.
