Even though earlier posts got a fair amount of traction, I completely abandoned this genre after feeling personally dissed by Lena Dunham's belittling of travel guides during an episode of Girls. Anyway, I'm over it. Here are my picks for a fab day or two in Montauk, NY all rolled up into a loose itinerary. (PS you might notice that these recommendations match very closely to other's. That bc there are only like 10 establishments out there. Quality not quantity.)
Where to Stay
Preface: Most places generally sell out well before the start of the summer season and/or require a two-night min on weekends. Going right before Memorial Day or right after Labor Day is a good option. That said, if your looking to venture out during prime time, I recommend calling around as there are always cancellations, and you won't get very far with most of the related 1997-style sites.
The Breakers is my go-to spot. Don't get too sketched out by the pics. It's clean, relatively inexpensive, and right across the street from the beach. They also have a pretty badass retro motel sign for photo ops.
Camping at Hither Hills could also be super fun, but it very crowded in Summer and booking is COMPETITIVE. No joke, you need to book that shit a year in advance. Makes sense since it's only $35/night and right door are $500+/night hotel counterparts. If you're up for an adventure, you can just show up here early on a Saturday morning (like 5 am early) and, again, ask about cancellations. There are about 2-3 last minute openings every week, but 8-10 cars waiting to jump on them.