All Aboard for a Key West Bachelorette!


All Aboard!

For Heather’s bachelorette, we boarded the Key West Express early on Friday morning from Fort Myers and set sail to Key West. The journey is quick 3 hours complete with various seating areas, TV, bar, and restaurant!

While you can also travel to Key West by car (head south until you hit Mile Marker 0) or fly into Key West International Airport, we recommend taking the Key West Express. 

The drive from even Miami to Key West is miserably long.

Travel can be exhausting, and no one wants to start off an exciting trip by wasting time in the car! Getting to Key West by boat is more fun and can start off the bachelorette party with a bang.

Key West Express
Hot Mess Express Group Riding The Key West Express

Where We Stayed

We stayed at our adorable rental property called Oliva by Duval, which features 3 houses with 11 rooms. It is great for larger groups! We rented one room (2 beds, 1 bath and brought an air mattress) that opened up to the pool courtyard!

This courtyard definitely came in handy when we were all a little hungover. Plus if you have any early wakers in the group, it’s a nice to have a pool outside so they can start their day without waking everyone.

Olivia by Duval Pool Deck

Bachelorette Party Itinerary


  • Travel to Key West – We highly recommend the Key West Express
  • Check into the rental
  • Sit poolside and sip cocktails
  • Dinner at Santiago Bodega followed by dessert at Better than Sex
  • Bar Hopping Night on Duval Street! Here are some bars we recommend:
    • Irish Kevins – popular bar with live music
    • Garden of Eden – clothing optional bar
    • Durty Harrys – live music every night
    • Sloppy Joe’s Bar – oldest bar in Key West


  • Explore Key West via bicycles (most properties offer them or you can rent them)
  • Some points of interest:
    • Southernmost Point – prime picture taking spot! Also famous Key West icon.
    • Little White House – They do tours, if you’re into that sort of thing
    • Hemingway House
    • Mallory Square – This is always rated for the best place to see the sunset and also has great shopping!
    • Key West Lighthouse
  • Grab a light lunch while out and about
  • Kino’s Sandals – Because we are typical Floridians, we LOVE stopping into Kino’s Factory. We have several pairs and wear they almost daily.
  • Dress Up Night/ Theme Night: Pink Ladies
  • Dinner at one of the many great places in Mallory Square
  • Drag Show at 801 Bourbon Street or Aqua (Be sure to make a reservation)


  • Brunch at Blue Heaven
  • Hang out poolside at Dante’s. This is a pool and tiki bar right next to the Key West Express Port. It’s a fun way to spend your last couple hours before your board the boat!
  • Head home!
Key West Southern Most Point

Themes, Shirts & Swag


The Maid of Honor selected the cutest theme for our second night, Sandy and the Pink Ladies. Heather made for one super HOT Sandy! We paired our Pink Ladies jacket with black tights and some 1950’s inspired accessories!

The Bride Dressed as Sandy and Bridal Party as The Pink Ladies
The Bride Dressed as Sandy and Bridal Party as The Pink Ladies


Our nautical inspired shirts were made by a local designer perfect to wear on the Key West Express and out exploring.

Here are a few other example saying’s if you’re hosting a beach, boat or Keys bachelorette party:

  • Beachin’ bride and Beachin’ babe
  • Last Crawl Down Duval
  • Aloha Bride and Aloha Beaches
  • Ship Faced
  • Trading My Tail for a Veil and Time to Party Our Tails Off (mermaid theme)
  • Good Times and Tan Lines
  • I’m the Main Beach and Shell Yeah, Let’s Party
  • Sun, Sand and a Ring on My Hand and Sun, Sand and a Drink in My Hand
  • Last Sail before the Veil


The MOH also made all the party goers “emergency kits” which some much-needed items like:

  • Bottled Water
  • Ibuprofen
  • Hair Ties / Bobby Pins
  • Granola Bars
  • Makeup Remover Wipes
  • Travel Sized Sunscreen

We also all received koozies and stemless acrylic wine glasses as favors!

Budget Breakdown

If you have any great ideas for what should be added to a Key West bachelorette party itinerary, let us know in the comments below!

Based on 5 party goers and 1 Bride

Key West Express: $155, per person – if you travel on days other than the weekend it is cheaper. Also look out for their annual Black Friday sale!

Airbnb: $610 (two nights, one room, sleeps 5/6)

Drag Show: $20 in dollar bills for tips, per person

Koozie & Reusable Tumbler: $15 per person (Etsy)

Emergency Kits: $50 for all the supplies

Pink Ladies Jacket and Accessories: $25, per person

Custom Bachelorette Tanks: $18, per person (local crafter)

Total: $407/per person (plus meals/drinks)

**This is if you cover all of the Brides expenses

If you’re throwing a bachelorette party and need more ideas, be sure to check out our other trips or get some inspiration from our party ideas!

You can also learn more about us here!

2 comments on “All Aboard for a Key West Bachelorette!”

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