3-Day Key West Bachelorette Itinerary

Why Key West for a Bachelorette

Key West is what happens when you take Duval Street and shrink the rest of the world to 1.25 miles. Everything from your hotel to the bars to the boat ramp is walkable or a 5-minute golf-cart ride.

The vibe is more Margaritaville than rooftop pool. If your bride wants flip flops, Painkillers, and a pirate ship sunset cruise more than she wants bottle service, this is the right call.

Day 1: Arrive and Crawl Duval

Afternoon: Check in and Pool Time

Land at EYW (Key West International) by mid-afternoon. The airport is a 10-minute Uber from Old Town and rides run about $15 to $20 each way.

Drop bags at The Gates Hotel or Casa Marina and meet at the pool. Pre-game with poolside Painkillers and matching sashes for the photo before the night kicks off.

Evening: Sunset at Mallory Square

Walk to Mallory Square by 6:30 p.m. for the Sunset Celebration. Street performers, sword swallowers, and the actual sun going down over the Gulf are the show.

Grab a conch fritter cone from a cart on the way for $8.

Night: Dinner and the Duval Crawl

Dinner at Blue Heaven with a reservation made 3 weeks out. The yellowtail snapper at $34 and the Key Lime Pie at $14 are the orders.

Then start the crawl. Hit Sloppy Joe Bar for the live band, the Green Parrot for the dive-bar dance floor, and finish at 801 Bourbon Bar for the legendary drag show. Cover at 801 is $5 to $10 and the drag queens roast the bride mercilessly.

Day 2: Boat Day and Beach

Morning: Brunch and Coffee

If anyone is alive before 10 a.m., do Cuban Coffee Queen for breakfast sandwiches at $10 with to-go cafe con leche. Or push brunch back to 11 at Blue Heaven for the lobster benedict at $26.

Afternoon: Sandbar Tour

Book a half-day sandbar tour with Fury Catamaran or a private charter through Key West Paddle. The sandbar tour is roughly $135 per person and includes the boat, a cooler, and a drift snorkel stop. Private charters for 8 to 12 run $1,800 to $2,500 for a 4-hour trip.

Pack a waterproof speaker, a cooler with White Claws, and a bridal float that doubles as the photo prop.

Evening: Pool Recovery and Dressy Dinner

Back at the hotel by 5 p.m., shower, and head to La Te Da for dinner at 8. The grouper at $42 and the rosé list make this the dressy night of the trip.

Night: Drag Show and a Tiki Bar

Catch the late drag show at La Te Da or walk over to Aqua Key West for a more high-energy version. Finish with one Painkiller at The Rum Bar.

Day 3: Brunch and Bike

Morning: Brunch at Two Friends Patio

Late brunch at Two Friends Patio for the Bloody Mary bar at $14 and the famous karaoke if anyone is brave enough at 11 a.m.

Afternoon: Hemingway House and Photo Walk

Tour the Hemingway House at $19 per person and meet the 6-toed cats. Walk to the Southernmost Point Buoy for the requisite group photo. The line moves but plan 30 minutes.

Late Afternoon: Spa or Pool

Book mani-pedis at Nailtini, where every service comes with a complimentary martini, mimosa, or wine. Pedicures run $50 and you can book the whole group together.

Evening: Conch and Goodbye

Light dinner at Half Shell Raw Bar with the peel-and-eat shrimp at $24 and a final round of Pirate Painkillers. Walk back to the hotel and pass out before the 8 a.m. flights.

Budget Breakdown

Item	Per Person
Hotel (3 nights, mid-range, double occupancy)	$450
Flights (from a major hub)	$300
Sandbar tour	$135
Meals (3 dinners, 2 brunches, snacks)	$350
Bars and cover charges	$200
Hemingway, Nailtini, transport	$120
Estimated total	$1,555

Final Tips

• Book the sandbar tour the day you book flights. Saturdays sell out 6 weeks ahead in season.
• Hotels on Duval are loud. If your group is mostly going to bed before 1 a.m., book on Truman or Eaton instead.
• Skip the cars. Golf carts and walking are how Key West works, and parking is a nightmare.
• Bring 2 swimsuits per day. You will go through them.