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.
1 of
Filters
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
Tennessee Williams Museum
Tennessee Williams Museum — dedicated to the life and works of the famed playwright in Key West’s Little White House complex.
Key Largo
CrossFit Key Largo
CrossFit Key Largo — strength, conditioning & community workouts on the ocean side, MM 100.
Key Largo
Jacobs Aquatic Center
Key Largo’s aquatic destination—swim, splash, train or relax poolside.
Key West
Hammerhead Surf Shop
Style + surf gear in Key West’s Historic Seaport — top apparel, shades & beach vibes.
Marathon
Marathon Pontoon Rental
Explore the Florida Keys in style with premium, dog-friendly pontoon boat rentals!
Key West
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West is a historic oceanfront resort featuring elegant accommodations, beachfront amenities, and classic island charm.
Weddings Max
300
Meetings Max
550
Total Space
11000 sq ft
Largest Room
5000 sq ft
Key West
Sloppy Joe's Bar
A legendary Key West bar & live-music venue—Sloppy Joe’s offers tropical nightlife, cocktails, and island vibes since 1933.
Marathon
Coco Plum Beach and Tennis Club
Charming family-friendly beachfront resort in Marathon featuring tennis, marina access, and relaxing coastal villas.
Key West
ZEN by Karen Moore
ZEN by Karen Moore offers handcrafted jewelry inspired by intention, energy, and coastal living, available at retailers throughout the Florida Keys and at exclusive pop-up events.
Key West
Beached Bum Life
Beached Bum Life — laid-back beachwear, sunglasses & coastal essentials for seaside living.
Key West
Saltwater Angler
The Saltwater Angler — Key West’s premier outfitter for fishing charters, technical gear, and apparel.
Marathon
Seven Mile Fly Shop
Full-service fly shop and guide outfitter in Marathon, FL, specializing in bonefish, permit, and tarpon fishing.
Key West
Key West Swimwear
Key West Swimwear offers stylish bikinis, one-pieces, tankinis, cover-ups, and accessories from top brands—perfect fits for beach days, vacations, and summer looks.
