Start from Chokoloskee, a historic island community, and paddle to the Watson’s Place campsite on the Wilderness Waterway.

This route follows historic water trails, passing through mangrove tunnels and pristine estuaries. Along the way, paddlers encounter wildlife, including alligators and sea turtles. Watson’s Place was once home to the infamous pioneer Edgar Watson, whose past adds a historical element to the experience.

Backcountry campsite, freshwater well, shelter from strong currents.

Depart from the Gulf Coast Visitor Center in Everglades City for a manageable 5-mile loop around Sandfly Island.

Perfect for intermediate kayakers, this trail showcases tidal flats and mangrove forests while providing excellent fishing opportunities. Native American shell mounds found on Sandfly Island hint at the deep history of the region.

Shorter-distance route, tidal-driven experience, picnic-friendly island.

Launch from Goodland or Marco Island and paddle toward Cape Romano’s striking abandoned dome homes.

The eerie, futuristic-looking dome structures, slowly being reclaimed by the sea, create an unforgettable sight. The surrounding waters offer excellent opportunities for dolphin sightings and snorkeling.

Landmark photography spot, clear water areas, remote beach access.

The Calusa people once thrived in this area, constructing massive shell mounds still visible today on some islands.

Tides and wind conditions strongly influence paddling here; outgoing tides can make return trips challenging.

November through April, when temperatures are cooler and bugs are less aggressive.

Waterproof maps, GPS, insect repellent, sunscreen, at least one gallon of water per person per day.

From Miami, take US-41 west for about 80 miles to Everglades City (approx. 1 hour 45 minutes).