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

Pinfish Entertainment

Florida Keys' top spot for family fun with bowling, axe throwing, arcade & more!

Meetings Max
192

Islamorada

Three Waters Resort & Marina

The old Postcard Inn at mile marker 84, reborn in 2024 as a 214 room Tribute Portfolio resort across 15 waterfront acres, with three pools, three beaches and a 72 slip marina. The Cove is the adults-only half, 63 king rooms around a private beach lagoon.

Meetings Max
120
Total Space
1680 sq ft
Largest Room
1680 sq ft

Islamorada

Sea La Vie Beach Boutique

Se La Vie Beach Boutique is your go-to island-vibe boutique for chic, seaside-inspired fashion and lifestyle essentials.

Islamorada

Mangrove Marina

Full-service marina in Tavernier offering wet slips, dry storage, houseboat rentals & resort amenities in a protected mangrove setting.

Islamorada

White Waters Paradise Bait & Tackle

Open at 7 every morning, seven days a week, at mile marker 74.5 with live shrimp and crabs in the tanks and everything you need for lobster season. It shares a roof with Lobster Walk, so you can buy bait on the way out and dinner on the way back.

Islamorada

Reef Roamer Catamaran Snorkel Sail

Reef Roamer Catamaran Snorkel Sail is a family-owned, 44-foot sailing catamaran that has run reef trips from Old Conch Harbor in Tavernier since 2006. It offers morning and afternoon snorkel sails plus a sunset sail, with gear included and an easy staircase ladder that lets snorkelers of all ages get into the water.

Islamorada

Crustacean Plantation

Crustacean Plantation Inc. is a nonprofit sanctuary in Tavernier dedicated to conserving native Florida Keys hermit crabs—known as "Purple Pinchers"—through habitat support, education, and community outreach.

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

Michelle Nicole Lowe, Artist

Michelle Nicole Lowe painted the cover of the 2023 Keys Traveler, a watercolor marking two hundred years of the Florida Keys. She is a fifth-generation Conch whose great-grandfather sailed over from Green Turtle Cay, and she paints the fish, birds and old bridges she grew up around.

Islamorada

The Tipsy Octopus

The Tipsy Octopus — quirky souvenir & specialty shop in Islamorada, where island‑style treasures, art pieces and fun gifts meet a roadside stop filled with character.

Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.

Meetings Max
675
Total Space
16000 sq ft
Largest Room
10000 sq ft

Islamorada

Mission Wild Bird Hospital

Rescue, rehabilitate, and protect wild birds at Florida Keys' top sanctuary.

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 Bay Forever

Non-profit dedicated to preserving Florida Bay through restoration, advocacy, and education.

Islamorada

Forever Young Charter Company

Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.