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
Capt. Sterling's Everglades Tour
Captain Sterling's Everglades Eco-Tours offers personalized, small-group boat excursions through the Everglades National Park, Pennekamp Park, and Florida Bay, led by experienced guides passionate about wildlife conservation.
Key Largo
RR Island Boutique
Stylish, affordable women’s boutique in Key Largo — RR Island Boutique
Key West
Shade Ceramics and Shutter Photography
Shade & Shutter Key West is a serene, artisan gallery where handcrafted ceramics meet evocative nature photography.
Key West
Bliss Jewelers
Bliss Jewelers is a family-owned luxury jewelry boutique in Key West, offering a curated selection of fine jewelry and timepieces from renowned brands like Omega, Breitling, and Tag Heuer.
Key West
Edward B. Knight Pier
Popular with residents and tourists alike, the Edward B. Knight Pier is dog-friendly!
Key West
Cora Beth Fishing
Cora Beth Fishing offers personalized, limited-load party boat and private fishing charters from Key West Bight Marina.
Key West
Key West Seaplane Adventures
Soar over crystal waters and land on the Gulf—Key West’s premier seaplane tours to Dry Tortugas and beyond.
Marathon
Kingsail Resort
Kingsail Resort offers waterfront accommodations with marina access, free kayak rentals, and a lagoon-view pool in Marathon, Florida Keys
Islamorada
DRIFT Island Collective
DRIFT Islamorada // Island Collective — thoughtfully curated coastal apparel & artisan goods in Islamorada, where island style meets relaxed living.
Key West
The Water Traveler Vacations
The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
Key Largo
Jimmy Johnson's Big Chill
Waterfront dining & live music 7 nights a week at Key Largo’s bayside hotspot.
