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.
Paddle through scenic mangrove tunnels with expert guides and spot local wildlife in a small group setting.
Spot gentle manatees and Everglades wildlife on a relaxed 90-minute covered boat cruise
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.
Catch and release in calm backwaters, spot manatees and alligators, and enjoy family-friendly fun
Experience wildlife, beach time, and shelling on a private boat tour for your group.
Experience wildlife and beach time on a 3-hour eco-tour through the 10,000 Islands.
Experience a half-day fishing adventure with all equipment and licensing included.
Experience a guided boat tour to spot manatees and wildlife in the Everglades with your group.
Experience a private sunset cruise with chances to spot manatees, dolphins, and more in the Everglades.
Catch fish among mangrove-lined islands on a 2.5-hour trip with all gear provided.
Experience a sunset cruise with chances to spot manatees, dolphins, and wildlife in the Everglades.
Spot dolphins and manatees, then relax on a secluded 10,000 Islands beach in a smooth-water eco cruise
Discover rare seashells with expert guides on secluded Southwest Florida islands
Discover rare shells and marine life on a private guided adventure through the Ten Thousand 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.
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.
Enjoy flexible four-day rentals with free delivery to your home or rental property.
Enjoy flexible five-day rentals delivered to your property for easy water adventures.
Cruise the Ten Thousand Islands on a private tour to discover wildlife and gather tropical seashells.
Enjoy flexible six-day rentals delivered to your property for easy water adventures.
Enjoy flexible three-day rentals with free delivery to your home or condo for easy water adventures.
Enjoy flexible weekly rentals delivered to your property for easy water adventures.
Enjoy flexible two-day rentals with free delivery to your home or rental property.
Search remote island beaches for rare seashells with expert local guides.
Enjoy a customizable private boat tour exploring Marco Island and the 10,000 Islands with your group.
Enjoy a customizable private boat tour for your group with expert guides and luxury amenities.
Spot playful dolphins and collect exotic shells on a guided mangrove cruise.
Enjoy a full day exploring islands, wildlife, and local spots with your group on a private boat tour.
Customize your cruise through hidden islands with expert captains, music, and luxury amenities for up to 17 guests
Explore Marco Island waterways at your own pace with free gear delivery to your door
Cruise the Ten Thousand Islands, spot dolphins, and collect exotic shells on a 2-hour family-friendly adventure
Spot playful dolphins up close on a 2-hour guided boat trip with guaranteed sightings.
Explore mangrove tunnels and channels at your own pace with included maps and gear.
Spot playful dolphins in their natural habitat on a guided 2-hour cruise.
Explore mangrove tunnels and channels at your own pace with included maps and gear.
Explore mangrove tunnels and channels at your own pace with included maps and gear.
Watch dolphins and hunt for shells as you cruise to a secluded beach for a Gulf Coast sunset
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.