The prime times to be out on the water and chasing huge stripers is from late June until early October.  The mystique of night fishing for stripers is magical and this is my favorite time on the water, as often my vessel will be the only one out there.  Summer nights in July and August are wonderfully productive as the weather is normally stable. These calm conditions are optimal for perfectly presenting a bait to the wily, cow sized bass that will be making Montauk waters their summer feeding zone.

I also enjoy angling for other local gamefish, especially bucktailing for
doormat fluke, and if this interests you then Montauk once again is the place to be.  In my opinion any day the fluke season is open one could go out onto these fabled waters and catch the fluke of your dreams  If you really want to tilt the odds in your favor then come out and fish with me in Mid-May or August and you'll have a great opportunity at catching multiple fluke in the jumbo to doormat size range. 
-Captain Tom Mikoleski