Discover amazing Chokoloskee activities and premium in-home experiences.
Nestled at land’s end where the Everglades meet the Gulf, Chokoloskee is a timeless island community steeped in Old Florida mystique. Here, pelicans drift by weathered docks and sunrises paint endless mangrove horizons—a place where life ebbs with the tides and quiet adventure lingers on every salty breeze. Chokoloskee invites those seeking wild beauty and deep tranquility to slow down and sink into its swamp-country soul.
Meet alligators, tigers, otters, and more in a 30–45 minute sanctuary visit
Reserve a private boat for your group of 7 or more and explore the Everglades in search of manatees and wildlife.
Experience a sunset cruise with chances to spot manatees, dolphins, and wildlife in the Everglades.
Experience a private sunset cruise with chances to spot manatees, dolphins, and more in the Everglades.
Spot dolphins and manatees, then relax on a secluded 10,000 Islands beach in a smooth-water eco cruise
Experience wildlife, beach time, and shelling on a private boat tour for your group.
Spot gentle manatees and Everglades wildlife on a relaxed 90-minute covered boat cruise
Catch fish among mangrove-lined islands on a 2.5-hour trip with all gear provided.
Experience a half-day fishing adventure with all equipment and licensing included.
Catch and release in calm backwaters, spot manatees and alligators, and enjoy family-friendly fun
Experience a sunset cruise with chances to spot manatees, dolphins, and wildlife in the Everglades.
Relax on a private pontoon to Keewaydin with BYOB and beach gear included
Discover hidden island beaches, collect rare seashells, and watch wild dolphins on a guided small-group boat trip.
Explore secluded beaches, collect shells, and watch playful dolphins on a scenic Naples boat trip
BYOB private tiki cruise for up to 26, with beach time or wildlife watching, offered in 3 or 6 hours
Sail a private tiki boat to admire Port Royal mansions, spot wildlife, and toast the sunset.
Cruise the scenic canals of Port Royal and enjoy a relaxing guided boat tour.
Spot wild dolphins and comb remote islands on a private 2.5-hour cruise tailored to your group
Search shifting sandbars near Kice Island for standout shells on a relaxed, family-friendly boat outing
Design a private two-hour cruise to spot dolphins, shell, and explore the Ten Thousand Islands
Discover Marco Island's history and wildlife on a guided 2-hour cruise
Soak in golden hour on the Gulf with dolphin watching and a beach stop
Spot wild dolphins on a 2-hour cruise through the Ten Thousand Islands
Explore mangrove estuaries, spot dolphins and birds, and enjoy shelling on a secluded island
Reach remote islands and the best shelling beaches on a 2.5-hour tour; private charters available
Discover rare shells and marine life on a private guided adventure through the Ten Thousand Islands.
Discover rare seashells with expert guides on secluded Southwest Florida islands
Discover rare seashells with expert guides and enjoy a comfortable boat ride through Southwest Florida’s islands.
Capture close-up encounters with dolphins on a private 2–3 hour charter for up to six guests.
Effortlessly explore mangroves by pedal kayak on a relaxing 2-hour eco-tour
Glide through calm mangrove tunnels and learn about the coastal ecosystem on an easy, all-skill-levels tour
Explore Rookery Bay's wildlife-rich waterways with a biologist guide on a small-group 3-hour cruise
Explore hidden mangrove tunnels and mudflats with a biologist guide for a unique wildlife adventure.
Explore remote Keewaydin Island with a biologist guide and find unique shells on a secluded beach.
See birds return to Rookery Bay’s rookery at sunset on a guided cruise with a biologist captain
Enjoy a customizable private boat tour for your group with expert guides and luxury amenities.
Customize your cruise through hidden islands with expert captains, music, and luxury amenities for up to 17 guests
Spot playful dolphins and collect exotic shells on a guided mangrove cruise.
Paddle calm estuarine waters with a naturalist guide to spot birds, manatees, and dolphins
72-hour kayak, paddle board, or fishing gear rental with free delivery on Marco Island, Goodland, and Isles of Capri
Chokoloskee is a small island community that captures the essence of Old Florida with its unique blend of natural beauty and cultural history. Located at the edge of Everglades National Park, this hidden gem offers visitors an opportunity to experience untouched wilderness and rich local traditions. The sun casts a golden glow over mangrove forests while gentle ocean breezes carry whispers from days gone by.
Begin your adventure in Chokoloskee by exploring Ten Thousand Islands on a guided kayak tour. Glide through serene waters as dolphins play nearby, or watch for manatees surfacing gracefully beside you. For those seeking more excitement, embark on an airboat ride across expansive wetlands teeming with wildlife like alligators and exotic birds—a true spectacle against vast blue skies.
History enthusiasts will appreciate visiting Smallwood Store Museum where artifacts tell stories about pioneers who once thrived here amidst challenging conditions. As evening falls upon this tranquil oasis, savor fresh seafood at one-of-a-kind eateries overlooking picturesque sunsets reflecting off calm bay waters—moments that linger long after your visit ends.