The Ultimate Guide to a Key West Girls’ Trip

Sun-soaked days and frozen drinks? Say no more. Whether you’re planning a bachelorette, birthday escape, or just a much-needed girls’ getaway, Key West delivers on all fronts. From pastel streets and buzzing beach bars to island adventures and late-night dancing, this corner of the Florida Keys has everything you need for an unforgettable trip with your favorite crew.

Here’s your no-stress guide to planning the ultimate girls’ trip to Key West.

Where to Stay

When it comes to the ultimate girls’ trip basecamp, Blue Flamingo Resort checks every box. Located just minutes from Old Town and Duval Street, it’s close enough to the action—but tucked away enough to actually relax. Our newly renovated double bedrooms and suites are perfect for friends, with plenty of space and comfort for everyone. Spend the day lounging at one of our two pools, then take our complimentary guest shuttle into Old Town—or stay poolside for live music, happy hour specials, and fun.

What to Do: From Day Drinks to Sunset Sails

Hit the Pool

Ease into island time with a pool day at one of Blue Flamingo’s two pools—weekends here are always lively with DJs, luxury cabanas, and weekend pool parties.

Brunch Hard

Fuel up with avocado toast and mimosas at hot spots like Blue Heaven, Harpoon Harry’s, or Toasted Coconut, located on property. Don’t be surprised if breakfast turns into a boozy brunch.

Explore Duval Street

It’s iconic for a reason. Duval is packed with bars, shops, and live music at any hour. For a classic crawl: start with frozen drinks at Fat Tuesday, pop into Sloppy Joe’s, and end with drag karaoke at Aqua.

Take to the Water

Book a private catamaran or sunset sail with champagne and snacks. For something more active, try paddle boarding, a sandbar cruise, or jet ski tour. Fury is the number one company to look to for all things on the land and water.

Snap the Perfect Photo

Don’t miss: the Southernmost Point buoy, pastel conch houses, murals on Petronia Street, and that golden-hour glow on the docks.

Hang at The Backyard

Grab lunch (and margs) while lounging in The Backyard. From zesty tacos to pizza and burgers, the food scene here from one of our two venues, Toasted Coconut and Rum Row, is worth sticking around for. Expect all the lawn game favorites—shuffleboard, bocce, cornhole, ping pong, and more.

Catch the Sunset at Mallory Square

This nightly celebration features performers, cocktails, and crowds gathering to watch the sun dip below the Gulf. It’s a must—show up early for the best view.

Break a Sweat

Start your day with a beach walk along Smathers, or break a sweat at FYT Key West—a local favorite studio nearby. From mat Pilates to HIIT, it’s our go-to for a fun group workout.