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.

Filters
Keys Season Deals
Destination
Category
Islamorada

Islamorada Fishing Charters Florida Keys

Offshore and inshore sportfishing charters in Islamorada.

Islamorada

Blackbeard Private Charters

Blackbeard Private Charters offers personalized boat excursions in the Florida Keys, including trips to the Islamorada Sandbar, snorkeling at Alligator Reef, sightseeing, and sunset cruises.

Islamorada

The Caribbean Resort

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Islamorada

Foraged Living Floral Atelier + Boutique

Handmade floral design, vintage decor & regionally sourced treasures in Islamorada.

Islamorada

General Store At Caloosa Cove Marina

Oceanfront resort in Islamorada with suites, marina, pool, and on-site dining.

Islamorada

Ocean Drive Indoor Golf

Golf Ocean Drive offers indoor golf simulator bays for players of all ages and skill levels in a fun, climate-controlled setting in Islamorada.

Islamorada

Amber Waves Boutique

Amber Waves Swim is a boutique in Islamorada's Art District offering chic, functional swimwear and accessories designed to flatter every figure.

Islamorada

Indian Key Historic State Park

Historic island ghost-town accessible only by boat / kayak.

Islamorada

Florida Keys Dive Center

Three-dive adventures, snorkeling & scuba charters from Islamorada with courses & lobstering.

Islamorada

Florida Keys Outfitters Fly Shop & Guide Service

A fly shop and guide service in Islamorada since 1989, and home to a saltwater fly fishing school now in its 37th year. Among the instructors is Chico Fernandez, who has been fishing salt on a fly since the 1950s and designed three of the patterns already in your box.

Islamorada

History of Diving Museum

Explore the fascinating history and evolution of diving at the History of Diving Museum!

Meetings Max
50

Islamorada

Amiga Mia Home - Boutique

Amiga Mia Home is a women-owned boutique in Islamorada built inside a redesigned vintage travel trailer. It stocks artisanal, boho-chic home decor and personal accessories, from ceramic planters to woven macrame crossbody bags and other handcrafted pieces.

Islamorada

Otherside Boardsports

Otherside Boardsports in Islamorada offers lessons, rentals, and retail gear for paddleboarding, kiteboarding, winging, wake, foil & more.

Islamorada

David Wirth Gallery

David Wirth’s Wirth Gallery showcases striking marine sculptures, bespoke fish-hook creations, and unique slab wood art, all inspired by coastal life and craftsmanship.