My friends and I have fished the sound all of our lives and have caught plenty of nice stripers in it. Ask the guy what type of fishing you'll be doing. I like to chunk the out going tide at night, inshore this time of year. Hell, I like the incoming also. I don't think to many LI sound charters chunk or live line bunkers but you never know until you ask. Usually it's trolling or plugging. I'm not much for trolling but plugging for them can be fun.
That being said, If I were to charter a bass trip I would still opt to spend more and go out of Montauk. You have more of a chance of landing a fish of a lifetime, 50+ pounders are not uncommon. Down side is it will cost you double the $350 for just a 6 hour trip. Full tides, special nights or moon tides usually cost more. The guy I use offers a 3 trip discount but he is likely booked for the season. You have to book the good ones before the Rockland County Outdoor Expo.
For the amount you want to spend I would just do a party boat out of Montauk preferably drifting eels. Also try the same thing out of Connecticut fishing "The Race". Google "fishing the race connecticut" I'm sure you will find lots of info about how and when to fish there. One of the more well known party boat fleets of Montauk is
http://www.vikingfleet.com/ $85/per person and you can probably rent gear from them. They sell the rigs so you may want to buy your own before hand and save some bucks. The July 10th pool winner was 39.3 lbs. check the reports before you go, if you go.
PCBs are a fact if you eat them, but the fish out of Montauk and The Race are more apt to be ocean run. You can usually tell this by the fact that some of them will have sea lice on them. Lice supposedly mean fresh from the ocean fish, but even that is a debatable. Well let me stop here before I get even farther off topic.
Good luck however you decide to fish.
