Couple descending wooden ship-themed stairway with nautical decor.

Things to Do

In The Florida Keys, adventure is just a footstep (or paddle, or fin) away. Whether you’re chasing sunrise paddle-trips, sunset sails, or discovering hidden mangrove tunnels, there’s always something new to try. Museums, wildlife tours, water sports, quirky local events—every destination brings its own flavor of fun. These listings span every kind of experience: rugged and wild, soft and serene, absurdly beautiful. So map out some time, pack your curiosity, and let the Keys pull you in.

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Islamorada

Elena Madden Studio Gallery

Elena Madden paints water and light from memory, never from a photograph, in Conté crayon and acrylic layered until the surface seems to move. Her studio gallery sits in Islamorada's Morada Way arts district, and her 22-foot tarpon hangs in the lobby at Cheeca Lodge.

Islamorada

Saltwater Outfitters

Upscale clothing and fly fishing store with swimwear and brands such as Pelagic, Salt Life, Huk, and Columbia.

Islamorada

Islamorada Wine Co.

Cozy wine bar with charcuterie, craft beer & boutique wines.

Islamorada

Key Dives

Explore top-rated scuba diving and reef conservation adventures in the Florida Keys!

Islamorada

Why Knot Boat Rentals & Charters

Why Knot Exclusive Rentals — custom boat rentals and captained charters in the Florida Keys for your perfect day on the water.

Islamorada

Cayo Vida Marina

A small working marina on Old Highway at the top end of Islamorada, open from 6 in the morning for people who are actually going fishing. Live and frozen bait at the counter, charter boats on the dock, and Cayo Vida shirts on your way out.

Islamorada

Islamorada's Art on a Whim Gallery

Judith Chesher stocks her shop with work from around thirty Keys artists, and as she puts it, the Keys are full of artists doing all kinds of weird things. It sits in Rain Barrel Village, a few steps from a forty-foot lobster.

Islamorada

Captain Michael Fishing

Captain Michael Party Boat Fishing offers affordable, group-friendly deep-sea fishing trips aboard a 65-foot vessel, departing daily from Robbie’s of Islamorada.

Islamorada

Florida Keys Farmers Market

A lively weekly farmers market in Islamorada with fresh produce, local art, and live music.

Islamorada

Z Flight Watersports | Islamorada FL

Soar with Z-Flight Watersports—book your unforgettable adventure today.

Islamorada

Purple Pineapple Boutique

Walk into Purple Pineapple Boutique in Islamorada and you'll immediately feel like you've found your people. Owner Lisa has filled this Village Square gem with breezy resort wear, dresses, rompers, two-piece sets, the best denim in the Keys, tarnish-free waterproof jewelry with select locally made styles, exclusive Purple Pineapple candles, Marlin's Cocktail Co. products, and a heartfelt Crafts Against Cancer collection handmade by Lisa's mom Peggy — all in a warm, kid-friendly space with a play area for little ones and a shave ice truck just steps away.

Islamorada

La Jolla Resort

La Jolla Resort: Classic Keys charm, beachfront views, family fun!

Islamorada

Islamorada Mercantile

Lifestyle boutique with resort wear, gifts & island essentials.