A Maid of Honor HQ three-day sample
Gurney's pool-club days, rosé beach picnics, and lighthouse photoshoots
Montauk, NY carries 9 bachelorette-friendly nightlife venues and 8 curated daytime activities in this guide, with a 4.31-star Google average across 14 rated spots. The 3-day sample below anchors Friday at Duryea's Lobster Deck and Saturday night at The Sloppy Tuna.
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The three days
Day 1 · Friday
Day 2 · Saturday
Day 3 · Sunday
The shortlist
Live music venue with local bands and a laid-back surf vibe
Local craft brewery with outdoor patio and food trucks
Montauk's most legendary outdoor party bar with DJs and dancing
Morning pastries and coffee before a beach day
All-day cafe popular for brunch smoothie bowls and avocado toast
Upscale seafood at Gurney's with panoramic ocean views
Questions bridesmaids ask
Three days — fly in Friday afternoon, do the big dinner + nightlife Friday night, the signature daytime activity plus another dinner Saturday, and a late brunch Sunday before wheels up. Two nights works for drive-in groups; four only if the bride wants a full resort day.
Six to ten bridesmaids is the sweet spot — big enough for a proper reservation, small enough to share one rental home and one group dinner table without splitting the party.
Lock lodging four to six months out, dinners six to eight weeks out, and the headline activity once the group flight count is confirmed. Montauk lodging tightens fast in peak wedding season (April–June and September–October).
Budget $550–$1,100 per bridesmaid for a three-day weekend in Montauk, NY — that covers a shared rental home, two big dinners, one activity, and nightlife. Upgrading to a boutique hotel or a private chef pushes the per-person into $1,200–$1,800.
No — the destination guide at /montauk lists every venue. This page is a three-day sample itinerary you can hand to the bridesmaids on day one. The AI planner at /plan builds a fully personalized weekend around the bride.
This is the shared sample. The AI planner personalizes every hour around the bride — parallel tracks for the pregnant friend and the sober bridesmaid, a trip terms sheet for the group chat so nobody gets a Venmo surprise, and every venue lifted from the real Montauk catalog. Free. No card.
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