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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Islamorada
Old Conch Harbor
Dockside Rawbar & Grill in Upper Islamorada serves fresh local seafood with a market on site, plus water sports, fishing, and excursions. Call 305-853-1010.
Key West
Shooterz Pool Hall
Shooterz Pool Hall in Key West is a casual sports bar, restaurant, and lounge on Flagler Avenue where you can relax, play pool, watch the game, and join the fun on the Road to Vegas APA League.
Islamorada
Cigars In the Keys
Cigars In The Keys, located at Mile Marker 82 in Islamorada, offers a curated selection of premium cigars, including exclusive blends crafted by Yaxel Ortiz, in a relaxed, welcoming environment.
Key West
Cruisin’ Tikis Key West
Cruisin’ Tikis Key West offers fun, BYOB tiki-bar boat cruises—including sunset sails, swim-stop excursions, and eco tours—aboard floating tiki bars navigated by USCG-certified captains.
Marathon
Dolphin Connection
Interact with dolphins in their lagoon habitat and help support marine conservation.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key West
Florida Keys Flight Academy Key West
Florida Keys Flight Academy — flight training and scenic tours in Marathon, where aspiring pilots and adventure seekers soar over the stunning Florida Keys.
Key West
Green Turtle Charters
Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.
Key West
Island Memories
Island Memories is a quaint establishment nestled in the heart of Key West, FL, offering a unique experience for visitors and locals alike.
The Lower Keys
Paddlin' Madeleine - Paddleboard Tours & Rentals
Intimate paddleboard tours & rentals in Key West’s hidden waters
Key Largo
Key Largo Tiki Tours
Float, sip & unwind—tiki cruises and private charters in Key Largo’s waters.
Key Largo
Jimmy Johnson's Big Chill
Waterfront dining & live music 7 nights a week at Key Largo’s bayside hotspot.
