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A Maid of Honor HQ three-day sample

Bachelorette weekend in Annapolis.

Schooner sails, crab feasts, and harbor-town charm

Annapolis, MD carries 2 bachelorette-friendly nightlife venues and 7 curated daytime activities in this guide. The 3-day sample below anchors Friday at Cantler's Riverside Inn and Saturday night at Middleton Tavern.

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The three days

Friday through Sunday, hour by hour.

Day 1 · Friday

Arrival, dinner, first drink.

  • Afternoon: Flights into BWI (Baltimore/Washington Intl). Check into lodging — Annapolis Waterfront Hotel is the bridesmaid-favorite base for this trip. Getting-ready outfits on, bride in the center of the group photo.
  • 7:30pm · Dinner at Cantler's Riverside Inn — The definitive Annapolis crab pick since 1974, on Mill Creek (Crab house · $$$)
  • 10:00pm · First drink at Middleton Tavern — 250-year-old waterfront tavern with nightly live music + oyster bar

Day 2 · Saturday

The signature day.

  • 11:00am · Woodwind schooner sunset sail — 74' schooner into the Chesapeake with cocktails aboard (2 hr · $55–$90/pp)
  • 8:00pm · Dinner at Carrol's Creek Cafe — Spa Creek views of the Bay Bridge + city skyline (Chesapeake seafood · $$$)
  • 10:30pm · The main event — Pusser's Caribbean Grille — Painkillers on the City Dock waterfront deck Open late.

Day 3 · Sunday

The soft landing.

  • 11:00am · Brunch at Boatyard Bar & Grill — Award-winning crab cakes + a great raw bar (Seafood / raw bar · $$)
  • 2:00pm · Departure. Group photo before the airport run to BWI — roughly 30 minutes from the usual lodging cluster. Bride gets the window seat.

The shortlist

Top venues in Annapolis.

Middleton Tavern

250-year-old waterfront tavern with nightly live music + oyster bar

Pusser's Caribbean Grille

Painkillers on the City Dock waterfront deck

Cantler's Riverside Inn

The definitive Annapolis crab pick since 1974, on Mill Creek

Carrol's Creek Cafe

Spa Creek views of the Bay Bridge + city skyline

Boatyard Bar & Grill

Award-winning crab cakes + a great raw bar

See the full Annapolis destination guide →

Questions bridesmaids ask

Before she sends it to the group chat.

How many days do bridesmaids usually spend in Annapolis 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 Annapolis 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 Annapolis 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. Annapolis lodging tightens fast in peak wedding season (April–June and September–October).

How much does a Annapolis bachelorette weekend cost per person?

Budget $550–$1,100 per bridesmaid for a three-day weekend in Annapolis, MD — 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 Annapolis destination guide?

No — the destination guide at /annapolis 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 Annapolis 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 Annapolis catalog. Free. No card.

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