Key West Bachelorette Itinerary (3 Days)
A 3-day Key West bachelorette itinerary with hour-by-hour plans for a sunset sail, brunch, drag shows, and group logistics for 6 to 12 women.
Quick Answer
This 3-day Key West bachelorette itinerary runs a brunch-and-Duval evening on Friday, a private sunset catamaran sail on Saturday, and a snorkel-and-shopping Sunday. Base in a colorful Old Town cottage so the group walks everywhere with no car. Budget roughly $700 to ,300 per person for lodging, a shared sail, meals, and nights out. Book the sunset sail and the house first, since both fill fast in spring.
Before You Go
Book the Old Town cottage and the Saturday sunset sail before anything else, since both fill months ahead in spring and around Fantasy Fest in October. A cottage near Duval lets 6 to 12 women skip rental cars and walk to brunch, shops, and the marina. Fly into Key West (EYW) if fares work, or into Miami (MIA) and drive 3.5 to 4 hours down US-1. Coordinate a color palette for photos and split shared costs on a group app before arrival.
Day 1 (Friday)
Arrive by mid-afternoon, settle into the cottage, and stroll to the Southernmost Point buoy for a group photo around 4 p.m. Grab frozen cocktails at the Rum Bar, then browse the boutiques along Duval and Whitehead Street before dinner.
Have dinner around 7:30 p.m. in the garden at Blue Heaven, then catch the drag show at Aqua on Duval Street around 9 p.m. for a lively, photo-friendly night. Keep the evening walkable and easy, wandering between bars with the bride, since last call runs to 4 a.m. and no one needs to drive.
Day 2 (Saturday)
Start with a relaxed brunch at Firefly or Two Friends around 10 a.m., then spend the early afternoon by the pool or shopping. The centerpiece is a private sunset catamaran sail, roughly $600 to ,200 for the group, boarding around 5 p.m. with champagne, music, and the best photos of the trip.
Back at the dock by dusk, freshen up at the cottage and head to a nice group dinner around 8:30 p.m. at Latitudes or Santiago's Bodega for shared plates. Cap the night with cocktails on Duval or a quieter wine bar, depending on the bride's energy. Keep it flexible so the group can stretch it out or wind down.
Day 3 (Sunday)
Book a mid-morning snorkel trip to the reef around 9:30 a.m., roughly $60 to 10 per person, for clear turquoise water and easy group photos. It is the calm, pretty counterpoint to Saturday's sail and a great final memory on the water.
Back by early afternoon, do a leisurely lunch and last-minute shopping along Duval, then catch the Mallory Square sunset before a final dinner. Keep Sunday night light if anyone flies out Monday, and settle the group app tab before everyone scatters so no one is chasing payments after the trip.
Booking Checklist
Lock these before the trip so the weekend flows and the maid of honor is not coordinating on the fly.
- Old Town rental cottage near Duval, booked 4-plus months ahead
- Private sunset catamaran sail for Saturday, deposit paid
- Mid-morning reef snorkel trip for Sunday
- Dinner reservations at Blue Heaven and Latitudes
- Flights into EYW, or into MIA plus a rental for the US-1 drive
- Group payment app and a coordinated photo color palette
Keep Planning
Frequently Asked Questions
- Is a private sunset sail worth it for a bachelorette?
- Yes, a private sunset catamaran sail is the highlight of most Key West bachelorette weekends. It runs roughly $600 to ,200 for the group, often includes champagne and music, and gives you the best photos of the trip on calm, golden-hour water. Book it two weeks ahead on weekends, confirm whether drinks and light decorations are allowed, and tip the crew 15 to 20 percent. Split the cost on a group app.
- Where should we stay in Key West?
- Stay in an Old Town cottage or house near Duval Street so the group walks to brunch, shops, the marina, and nightlife with no car needed. It keeps 6 to 12 women together and cuts rideshare to zero. Expect roughly $250 to $500 per person for three nights sharing. Book four-plus months ahead for spring, since walkable Old Town rentals for a group are the hardest piece to secure late.
- What should we do besides the beach in Key West?
- Key West is more about the water and the streets than the beach, so plan a sunset sail, a reef snorkel trip, and plenty of strolling. Browse the boutiques on Duval and Whitehead, photograph the Southernmost Point buoy and pastel houses, catch a drag show at Aqua, and watch the Mallory Square sunset celebration. Brunch at Blue Heaven and Firefly rounds it out. Smathers Beach is fine for a quick swim.