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Montauk is easier to do, lots of places to stay. and pretty straight forward to get to, and they have booze.
Cutty is tougher, ferry only, no vehicles allowed, bring everything you need cause the island doesnt have much to offer thats affordable.
I went last year and it was a great trip, but expensive.
You need do to both.
Just remember just because your in the meccas of surfcasting doesnt gurantee anything!!
I spent 7 days in montauk with 10 other surfcasters fishing 10 to 14 hours a day all over and the fish was worst then awful.
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