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A Maid of Honor HQ three-day sample

Bachelorette weekend in Naples.

Yacht charters and Fifth Avenue polish

Naples, FL carries 3 bachelorette-friendly nightlife venues and 5 curated daytime activities in this guide. The 3-day sample below anchors Friday at Ocean Prime and Saturday night at Bar Tulia.

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The three days

Friday through Sunday, hour by hour.

Day 1 · Friday

Arrival, dinner, first drink.

  • Afternoon: Flights into RSW (Southwest Florida Intl). Check into lodging — Naples Bay Resort & Marina is the bridesmaid-favorite base for this trip. Getting-ready outfits on, bride in the center of the group photo.
  • 7:30pm · Dinner at Ocean Prime — Fifth Ave private dining + a Wine Spectator list (Seafood + steak · $$$$)
  • 10:00pm · First drink at Bar Tulia — Fifth Ave staple with house-infused spirits + Tuscan Mules

Day 2 · Saturday

The signature day.

  • 11:00am · Cool Beans 'Last Sail Before the Veil' cruise — Bachelorette catamaran cruise on the Gulf (3 hr · $60–$120/pp)
  • 8:00pm · Dinner at Chops City Grill — In-house aged steaks + craft cocktails (Steakhouse · $$$)
  • 10:30pm · The main event — Easy Tiger — Perry Hotel rooftop with a Lynnette Marrero cocktail program Open late.

Day 3 · Sunday

The soft landing.

  • 11:00am · Brunch at The Boathouse — Naples Bay waterfront brunch (Seafood · $$)
  • 2:00pm · Departure. Group photo before the airport run to RSW — roughly 40 minutes from the usual lodging cluster. Bride gets the window seat.

The shortlist

Top venues in Naples.

Bar Tulia

Fifth Ave staple with house-infused spirits + Tuscan Mules

Easy Tiger

Perry Hotel rooftop with a Lynnette Marrero cocktail program

Blue Martini

Dancing + live music at Mercato

Ocean Prime

Fifth Ave private dining + a Wine Spectator list

Chops City Grill

In-house aged steaks + craft cocktails

The Boathouse

Naples Bay waterfront brunch

See the full Naples destination guide →

Questions bridesmaids ask

Before she sends it to the group chat.

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

How much does a Naples bachelorette weekend cost per person?

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

No — the destination guide at /naples 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 Naples 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 Naples catalog. Free. No card.

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Naples destination guide →All FL bachelorette cities →All 3-day weekend samples →Build a weekend with the planner →