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.
On Island Time at Island Fest
Art, Crafts, Great Food.....Oh my!
From vintage cars to vibrant arts and crafts, at the Islamorada Island Fest March 28-28 you can spend your day savoring keys cuisine, listening to local live music or running into friends from across the island chain.
Get back to the roots of the islands
Afro Roots Fest in Islamorada
Experience a weekend April 3-5 that showcases the roots of the islands through music and the diverse cultures that have formed the communities and laid back vibe locals and visitors can't get enough of.
I would walk 120 miles
Explore the keys by foot
The Florida Keys offer numerous places to stretch your legs to explore the beautiful and unique natural ecosystems found throughout the chain of islands.
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Key Largo
Rainbow Reef Dive Center (Boats)
Rainbow Reef Dive Center is a top-rated PADI 5-Star Dive Center in Key Largo offering daily dive and snorkel trips, customized dive/hotel packages, gear sales and service, dive training, and full-service support for divers of all levels.
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
Maria Wagner Artworks
Painting with Maria — original tropical art & interactive paint parties in Islamorada, where island vibes meet creative expression.
Key West
Sunshine Apparel_1
Sunshine Apparel_1 — stylish, island-inspired clothing boutique in Key West.
Islamorada
Florida Keys Watersports
Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.
Key West
Key West Sunshine Club
Key West Sunshine Club is a Bahama Village boutique with curated apparel & accessories (women, men, kids), local-artist pieces, and its own clothing line.
Key West
Wilhelmina Harvey Park
Wilhelmina Harvey Park — a neighborhood rec park with playground, picnic area and walking trail on Big Pine Key.
Key West
Southernmost Trolley Stop
The southernmost trolley stop is in Key West, Florida, located at the iconic Southernmost Point buoy.
Key West
Rodriguez Cigar Factory
Explore Key West’s historic Rodriguez Cigar Factory & shop artisan cigars.
Key Largo
Key Largo Parasail
USCG-certified parasail adventures: soar over Key Largo’s waters in style.
Key West
Life On The Rocks Charters
Life on the Rocks Charters offers fun, customizable boat trips around Key West—sandbar hopping, snorkeling, sunset cruises, and more.
The Lower Keys
Sugar Loaf Lodge
Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.
