Offshore fishing out of eastern Long Island is not a longer version of a bay trip. It is a different activity with different rules, a different failure mode, and a much higher chance of being cancelled. Anyone selling it as a scaled up day out is not being straight with you.
The Distance and the Day
The canyon water south of Montauk sits roughly thirty miles offshore, sometimes further depending on where the fish are holding. Trips run twelve hours or more and some go overnight, partly because bigeye tuna often feed at night or in the first light.
Bigeye, mahi mahi, and shark are the targets, and the window is roughly July through October with late August into September usually the strongest stretch. That is the honest version. Nobody can promise a canyon trip produces.
The Rules Are Real and They Have Changed
Shark fishing out of New York is heavily regulated and most of what people think they know is a decade out of date.
Anglers targeting shark or tuna need a federal Highly Migratory Species permit. Retention is one shark per vessel per trip, not one per angler, with a narrow exception for a couple of small species. Shortfin mako, the classic Montauk shark, is prohibited, along with a long list of others that must stay in the water and be released immediately. Targeting a prohibited species at all is a violation. Allowed species carry size floors, and non stainless, non offset circle hooks are mandatory when fishing bait.
In practice that makes a modern shark trip a catch and release fishery. If you want a cooler full of fish, offshore is the wrong booking. If you want to fight something large and put it back, it is exactly the right one. Charters in The Hamptons runs private offshore trips out of Shelter Island and is straightforward about walking through the permit and retention rules before anyone books.
Seasickness Is the Part Nobody Discusses
Peconic Bay stays flat when the ocean does not. Thirty miles out there is no such protection, and twelve hours is a long time to be miserable.
the CDC’s guidance on motion sickness is worth reading before the trip rather than the morning of. The short version: susceptibility varies enormously between people, behavioural steps come first, and anything pharmacological needs to be taken well before symptoms start because once nausea sets in absorption stops. Stay on deck, keep the horizon in view, eat something before you leave the dock, and be honest with the captain when you book.
Weather Decides Whether It Happens
This is the single biggest difference between offshore and every other charter on the East End. The canyons are fishable only in a settled forecast, and late summer weather out there turns fast.
Groups that give a two or three day window get out far more often than groups locked to one Saturday. A captain worth booking will cancel a marginal day rather than take you thirty miles out into something ugly, and will tell you when a date is not realistic instead of taking the deposit. That trait matters more offshore than anywhere else.
Who Should Not Book It
Kids. First timers. Anyone who has never done a long day in open water. Groups where half the party is unsure. A half day inside the bay will produce more fish, more comfort, and more people who want to go again.
For everyone else, book early, keep the dates flexible, and pack more water and more layers than seems reasonable.