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
General Store At Caloosa Cove Marina
Oceanfront resort in Islamorada with suites, marina, pool, and on-site dining.
Key Largo
Largo Cargo Co.
Key Largo’s go-to gift & souvenir shop with tropical apparel, Key Lime treats, and beach gear.
Marathon
Skipjack Resort and Marina
Relax at Skipjack Resort & Marina in the Florida Keys—luxury suites, marina, pool, and fresh seafood!
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
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.
Marathon
Sunset Bay Park on Grassy Key
Sunset Bay Park (Grassy Key) — serene waterfront park on Grassy Key ideal for sunset viewing and island relaxation.
Islamorada
Amiga Mia Home - Boutique
Amiga Mia Home is a boutique in Islamorada offering artisanal home decor and personal accessories inspired by natural, organic, and boho-chic design.
Key West
Key West Community Sailing Center
Learn to sail and enjoy vibrant community events at Key West Sailing Center!
Key West
KINO Sandals
Handcrafted leather sandals, made in Key West since 1966 — classic styles for men, women & kids.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
Key West
Salty Dog Key West
Salty Dog Key West – iconic apparel & gift shop on Simonton Street, offering unique coastal gear, island-themed fashion, and pet merchandise.
Islamorada
Wild Dolphin Tours
Wild Dolphin Tours — intimate dolphin-watching and snorkeling excursions in Islamorada where wild pods, reef adventures and island calm meet.
Key West
Argo Navis Key West Sailing Charters
Argo Navis is a 75-foot luxury catamaran offering intimate, all-inclusive sailing experiences in Key West, including sunset cruises, brunch sails, and private charters, with curated food and drink pairings.
