Multi-Day Routes Through the Backcountry
Everglades City is one end of a 99-mile marked water trail that takes the better part of a week to paddle, and it is also a fine one-night stop on a much shorter road trip; the gap between those two trips is the entire point of planning ahead here.
The Wilderness Waterway, the real expedition
The Wilderness Waterway runs 99 miles through interior mangrove wilderness between Everglades City and Flamingo, typically taking 7 to 9 days of self-sufficient sea kayaking or canoeing. Paddlers sleep on chickees, elevated wooden platforms over open water, and on shell-mound or barrier-island ground sites; individual site availability shifts with storm damage and repair work, so check the current NPS wilderness trip planner rather than treating any single campsite as guaranteed open. A backcountry permit through Recreation.gov runs a $21 administrative fee plus $2 per person per night, and paddlers carry every drop of their own drinking water, since none exists along the route.
A shorter version, without the full traverse
For two to four days rather than a full week, the Ten Thousand Islands kayak-camping loop bases out of outer barrier beaches like Tiger Key, Picnic Key, Pavilion Key, and Jewell Key: uninhabited islands, surf fishing, dolphin sightings, and genuinely dark skies without the Wilderness Waterway’s full mileage. A boat-assisted kayak trip covers the outer-island approach for anyone who would rather skip the long open-water paddle out and still camp on the islands themselves.
The road-trip version, four days, no camping required
Day one in Naples or Marco Island; day two based in Everglades City for the park boat tour, a mangrove-tunnel airboat outside the park, and a stone crab dinner; day three east on Tamiami Trail through Big Cypress, ending at Shark Valley’s tram tour 50 miles away; day four into Miami or south toward Key Largo. This version needs a rental car and nothing else, and it links directly to the single-day version of each stop in the day trips guide .
Whichever route gets picked, the same rule applies at every boardwalk and canal stop along the way: hold at least 50 to 60 feet back from any alligator and never feed one, since it is illegal and it is what makes an alligator dangerous around people.
The verdict: the Wilderness Waterway is a serious backcountry undertaking that needs real paddling experience and a permit booked months out, while the four-day road circuit needs only a rental car and a hotel reservation, so pick based on honestly assessed paddling skill rather than ambition alone.