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 West
Hammerhead Surf Shop
Style + surf gear in Key West’s Historic Seaport — top apparel, shades & beach vibes.
Islamorada
The Tipsy Octopus
The Tipsy Octopus — quirky souvenir & specialty shop in Islamorada, where island‑style treasures, art pieces and fun gifts meet a roadside stop filled with character.
Key Largo
Captain Lew Charter
Key Largo private cruise on a 32' catamaran—snorkel, sunset, up to 6.
Islamorada
AquaBlue Adventures Sandbar Charter & Boat Tours
AquaBlue Adventures: Your go-to for expert-guided snorkeling, paddleboarding, and private eco-charters in the Florida Keys.
Islamorada
Sunrise Cuban Market & Cafe
Sunrise Cuban Cafe & Market — authentic Cuban cuisine, breakfast through dinner, right on the Overseas Highway in Tavernier.
Key West
Blue Horizon Charters
Blue Horizon Charters offers private boat adventures in Key West—ranging from sandbar escapes and snorkeling to sunset cruises—crafted by three lifelong friends passionate about island life and hospitality.
Key West
Key West Island Bookstore
Key West Island Books is a beloved independent bookstore in Old Town offering new, used, rare, & antiquarian books—including a strong selection by local authors, bestsellers & literary treasures.
Key Largo
Holiday Inn Key Largo
Holiday Inn Key Largo is a tropical hotel featuring two heated outdoor pools with a waterfall, a poolside Tiki bar, and an on-site marina.
Weddings Max
140
Meetings Max
140
Total Space
3070 sq ft
Largest Room
2400 sq ft
Key West
Beached Bum Life
Beached Bum Life — laid-back beachwear, sunglasses & coastal essentials for seaside living.
Key West
Oldest House Museum & Gardens Key West
Old Island Restoration Foundation — preserving historic buildings & culture in Key West since 1960.
The Lower Keys
Coupon Bight Aquatic Preserve
Coupon Bight Aquatic Preserve is a 5,400-acre protected area south of Big Pine Key, where vibrant seagrass beds, coral patch reefs, mangroves, and hard-bottom habitats support rich marine biodiversity.
Marathon
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Key Largo
Sandy Dreamz Boutique
A unique beach boutique offering "Beach to Bar" styles for her, boating adventure wears for him plus fun time items for the little ones and charming memorabilia to take home.
Marathon
Starfish Marathon Snorkeling Tours
Explore vibrant coral reefs and marine life on fun, family-friendly snorkeling tours in Marathon!
