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A Maid of Honor HQ three-day sample

Bachelorette weekend in St. Augustine.

Historic-district spa days, pottery studios, and fort photoshoots

St. Augustine, FL carries 8 bachelorette-friendly nightlife venues and 10 curated daytime activities in this guide, with a 4.50-star Google average across 16 rated spots. The 3-day sample below anchors Friday at Columbia Restaurant and Saturday night at The Ice Plant Bar.

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The three days

Friday through Sunday, hour by hour.

Day 1 · Friday

Arrival, dinner, first drink.

  • Afternoon: Flights into JAX (Jacksonville International Airport). Check into lodging — The Collector Luxury Inn is the bridesmaid-favorite base for this trip. Getting-ready outfits on, bride in the center of the group photo.
  • 7:30pm · Dinner at Columbia RestaurantSt. Augustine outpost of Florida's oldest restaurant — 1905 salad is iconic. (Spanish / Cuban · $$$)
  • 10:00pm · First drink at The Ice Plant BarCraft cocktails in a restored 1920s ice plant building with an industrial-chic vibe.

Day 2 · Saturday

The signature day.

  • 11:00am · San Sebastian Winery TourFree wine tasting in a converted East Coast Railway building downtown. (1 hour · $0–$10/pp)
  • 8:00pm · Dinner at Cap's on the WaterWaterfront seafood restaurant with Intracoastal views and fresh-catch specials. (Seafood · $$$)
  • 10:30pm · The main event — Ice Plant BarHistoric ice-house cocktail room — candlelit + seasonal cocktails Open late.

Day 3 · Sunday

The soft landing.

  • 11:00am · Brunch at The KookaburraQuirky Aussie-themed brunch with flat whites and smashed avo in the historic district. (Australian / Brunch · $$)
  • 2:00pm · Departure. Group photo before the airport run to JAX — roughly 55 minutes from the usual lodging cluster. Bride gets the window seat.

The shortlist

Top venues in St. Augustine.

The Ice Plant Bar

Craft cocktails in a restored 1920s ice plant building with an industrial-chic vibe.

4.7 · 4,305

Ice Plant Bar

Historic ice-house cocktail room — candlelit + seasonal cocktails

4.7 · 4,305

Prohibition Kitchen

Speakeasy-themed restaurant and bar on St. George Street with live music.

4.4 · 7,520

Columbia Restaurant

St. Augustine outpost of Florida's oldest restaurant — 1905 salad is iconic.

4.4 · 13,850

Cap's on the Water

Waterfront seafood restaurant with Intracoastal views and fresh-catch specials.

4.6 · 6,365

Osprey Tacos

Cash-only taco window with creative fillings — blackened mahi and birria.

4.7 · 1,708

Questions bridesmaids ask

Before she sends it to the group chat.

How many days do bridesmaids usually spend in St. Augustine for a bachelorette weekend?

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.

What is the right group size for a St. Augustine bachelorette trip?

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.

When should we book St. Augustine for a bachelorette weekend?

Lock lodging four to six months out, dinners six to eight weeks out, and the headline activity once the group flight count is confirmed. St. Augustine lodging tightens fast in peak wedding season (April–June and September–October).

How much does a St. Augustine bachelorette weekend cost per person?

Budget $550–$1,100 per bridesmaid for a three-day weekend in St. Augustine, FL — 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.

Is this weekend the same as the St. Augustine destination guide?

No — the destination guide at /st.-augustine 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.

Build her own St. Augustine weekend.

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 St. Augustine catalog. Free. No card.

Start her St. Augustine plan — free →