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
Natacha's Boutique
Natacha’s Boutique in Islamorada offers island clothing, handmade jewelry, coastal decor, hammocks, and hair braiding services.
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
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
Key Largo
Fischer and Sons Jewelers
Family‑owned jewelers offering custom designs, repairs, and gifts since 1954.
Key West
Besame Mucho
Besame Mucho is a romantic and curated boutique in Key West's Bahama Village, offering a lovingly selected array of bath & body products, fragrances, jewelry, vintage finds, and thoughtful gifts in an atmosphere that delights and calms.
Key West
Magie Ruley-Island Inspirations
Bright, tropical acrylic art by Key West painter Maggie Ruley — bold colors, island scenes, and happy vibes.
Key West
Clarence S.Higgs Memorial Beach Park
Higgs Beach Park in Key West features sandy beaches, turquoise waters, historic sites like Fort West Martello, a beachside café, a children’s playground, and recreational amenities including snorkeling, kayaking, and tennis.
Key West
Sunset Pier
Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.
The Lower Keys
Big Pine Key Park
Big Pine Community Park is a vibrant, waterfront recreation hub on Big Pine Key, offering tennis, basketball, bocce, a skate park, playgrounds, a fitness trail, and a spacious community center.
Key West
Astro City Playground
Astro Park Playground is a family-friendly outdoor recreation area in Key West featuring a playground, beach access, barbecues, and beach wheelchairs, open daily from 7:30 AM to sunset.
Key West
Millionaire Gallery
Millionaire Gallery specializes in high-end photography and fine art from world-class photographers, with locations in the Keys and online sales.
Islamorada
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
Key West
Simonton Beach Key West
Picturesque city beach on Simonton Street in Key West with easy access and tropical ambiance.
Islamorada
Cheeca Lodge & Spa
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.
Meetings Max
675
Total Space
16000 sq ft
Largest Room
10000 sq ft
