Montauk is not the Hamptons, and anyone from out here will tell you that with some pride. It's a fishing town, the last stop on the LIRR, and there is no Montauk photo without the ocean in it.
Three rooms, one road in, and a season that ends. Book the block before you book the band. Owners: claim your page free.
Be straight with yourself about the drive. From Nassau you're looking at two and a half hours on a summer Saturday, and past Amagansett there's one road in and no way around it. Your guests are making that trip too. The couples who pull off Montauk treat it like a destination wedding that skips the airport: a room block locked down early, a shuttle from the motels to the venue, and a plan for the people who rolled in Friday night. Montauk rooms are scarce and they know what they're worth in August.
Gurney's runs the whole weekend on the ocean side, the Montauk Yacht Club holds the harbor, and Navy Beach puts the party right on the bay sand at sunset. That's a short list on purpose. Montauk doesn't have forty venues, it has a handful that do it well, and they book the summer out a year ahead.
July and August put you up against tourist rates and a town running past capacity. Come late September, Montauk goes back to being a fishing town, the surfers get the water to themselves, and a venue that quoted you August money will suddenly talk. If your heart is set on getting married out there, set your date around Montauk's calendar instead of fighting it.
Nobody drives three hours for five hours of party, so give them a weekend. A welcome gathering at a clam bar Friday, the wedding Saturday, a lazy beach morning Sunday before the caravan heads west. Put the whole plan on one card in the welcome bags and your phone stops ringing. The other rule: tell guests to book rooms the day you book the venue, not when the invitation lands, because the motels sell out August by spring and the ones who wait end up sleeping in East Hampton and grumbling about it.
The wind out there is a member of the wedding party, so pin the veil, mic the vows or nobody past the third row hears them, and know that Montauk tents get engineered, not just decorated. What you get for the trouble is the reason people make the drive: the open Atlantic in every frame, cliffs instead of hedges, and a wildness the manicured end of the Island can't fake. Montauk doesn't do polished. That's the point of Montauk.