If you love to fish, Montauk is the place to be. I recently saw an ad somewhere that described Montauk as a "quaint little drinking village with a fishing problem" and that's about as good of a description as any. A number of boats down at the harbor are ready for hire to take you and your group on daily tours to catch whatever is in season. I am hoping that maybe this summer or fall I can convince my family to go out with me, I think it would be cool!
Lenny's is a great spot to grab lunch, watch them all come back in, and check out the catch of the day. If you want to charter your own boat or dock your boat there are a number of marinas nearby, including the Gone Fishing Marina, Rick's Crabby Cowboy Marina, the Montauk Marine Basin, and Uihlien's Marina. The Montauk Yacht Club and Star Island Yacht Club are also available for dockage, and Star Island has a number of shark tournaments in the summer months. I am hoping to check out the upcoming one in June-- watch out JAWS, here I come!