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Clear allTwo pubs by the water handle birthdays in Jacobs Well, and guest numbers will usually settle which one you ring first. Montauk Tavern looks over Calypso Bay Marina, while Jacobs Well Hotel spreads a party across four separate spaces.
How the pair differ for a birthday crowd:

Jacobs Well Hotel lists a lawn marquee for up to 200 and a beer garden for 400, so that number sits comfortably there. No figure is given for Montauk Tavern, so ask the events team about its marquee.
Yes. Montauk Tavern says long lunches can be arranged and the kitchen serves all day. It trades from 10am to midnight daily, so a daytime booking is easy to raise.
Jacobs Well Hotel has large screens, a stage and microphones across its spaces. Montauk Tavern does not list that gear, so ask before you build a slideshow around it.
Ask what format suits your numbers. Jacobs Well Hotel offers food stations, canapés, buffets and a shared banquet, and the banquet needs at least 30 guests. Montauk Tavern shapes food and beverage packages to each event.