Share the wild coast with shorebirds and marine life on this 50-mile loop. Park at the Gulf Coast Visitor Center, pick up permits, and file a trip plan (you should have intermediate paddling and navigation skills). Launch from the boat ramp and head southeast along the shore on a three-mile paddle to the town of Chokoloskee. Continue southeast 3.5 miles to Wilderness Waterway marker 127, then turn Gulfward to pick your way through the mangrove maze of Rabbit Key Pass. Go past the white-sand paradise of Turtle Key before the .3-mile crossing to Rabbit Key. Lunch on shellcovered shores before heading southeast for the 3.7-mile crossing to Pavilion Key’s long, sweeping beach. Make camp on the island’s northeastern side.

The next day, head southeast between two mangrove-covered islands, then it’s an 8.2-mile open ocean crossing to Mormon Key. Follow the shoreline to the mouth of the Chatham River, then snake up sandbar-lined waterways to the upland campsite at Watson Place. (Tip: Gather wood for a fire to ward off bugs.) Continue .6 mile up the river on day three and veer left at the major fork. Continue until the water opens into Last Huston Bay and the Wilderness Waterway. Paddle northwest, reaching Sunday Bay in 3.2 miles, then turn north to the Sunday Bay Chickee, an elevated tent platform (with outhouse!).

On the final day, head east-northeast to the Wilderness Waterway marker 125. Paddle across Cross Bay, Shoal Mud Bay, and Hurdles Creek, then head west to the Turner River  and Chokoloskee. Take the canal for a lazy two-mile cruise toward Everglades City, then turn under the causeway bridge to reach the ranger station.

Permits: Reserve campsites 24 hours in advance (November-April). (239) 695-3311; nps.gov/ever

Gear Up: Rent kayaks, paddles, spray skirt, PFDs, and pumps from Saltwater Sports: (239) 262-6149; saltwatersportsflorida.com.