A Maid of Honor HQ three-day sample
Gatsby lawns, Montauk surf, and rosé that never runs out.
The Hamptons, NY carries 7 bachelorette-friendly nightlife venues and 8 curated daytime activities in this guide, with a 4.30-star Google average across 1 rated spots. The 3-day sample below anchors Friday at Duryea's Lobster Deck and Saturday night at The Surf Lodge.
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The three days
Day 1 · Friday
Day 2 · Saturday
Day 3 · Sunday
The shortlist
Montauk's iconic waterfront lodge hosts live music on the dock every summer evening — the single best place to watch the sun drop into Fort Pond Bay.
Bohemian Montauk motor lodge turned summer cocktail destination with a campfire pit, string lights, and an effortlessly cool crowd.
Italian-accented wine bar where the aperitivo hour runs long, the negronis are perfectly stirred, and every table looks like a Vogue editorial.
Lobsters pulled from traps in Montauk Harbor and served at weathered picnic tables with sweeping water views — the definitive Hamptons lunch.
The Hamptons institution since 1988 — wood-fired Tuscan cooking and a regulars list that includes everyone who's anyone from June to Labor Day.
Tom Colicchio's farm-to-table restaurant inside a Greek Revival mansion with produce from its own kitchen garden — elevated and deeply seasonal.
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. The Hamptons lodging tightens fast in peak wedding season (April–June and September–October).
Budget $550–$1,100 per bridesmaid for a three-day weekend in The Hamptons, 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 /the-hamptons 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 The Hamptons catalog. Free. No card.
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