If advanced paddling routes are what you crave, the possibilities are wide open. Try any leg of the trail.
Among the hotspots:
Estero River: Launch from Koreshan State Park or Estero River Outfitters and paddle downstream, into Estero Bay and to Mound Key. Allow at least six hours.
Captiva: Paddle the backside of Buck Key to the J.N. "Ding" Darling National Wildlife Refuge on Sanibel with a break at Blind Pass on the way back. Allow four to six hours.
Pine Island: Drop off a car in Bokeelia, then shuttle back to Matlacha, where you can launch and paddle northwest via Indian Field and Smokehouse Bay, then cut in at Jug Creek Allow five to six hours.
Two-day trip: Leave from Pineland or Jug Creek Cottages and paddle with camping gear to Cayo Costa State Park (make reservations); return the next day.
Many sections of the trail have protected waters that are comfortable when the wind is blowing.
Among the options:
Lovers Key: Launch from this Fort Myers Beach-based state park and sample the Blueway in one hour or less.
Bunche Beach: From this south Fort Myers preserve, try looping around the mangroves behind the beach for protected water; or take two hours and head to Hell Peckney Bay.
Manatee Park: The east Fort Myers park’s launch site is on a protected canal that leads to the Orange River, a tame, slender tributary of the Caloosahatchee.
Tarpon Bay: Part of the J.N. “Ding” Darling National Wildlife Refuge, this body of water is relatively protected from wind. It also features the Commodore Creek Canoe Trail, which takes paddlers on a gentle two-hour adventure.
Another source of day-trip ideas for paddlers is at the Florida Circumnavigational Saltwater Paddling Trail, http://www.floridadep.org/gwt/paddling/saltwater.htm. Click on Segment 12/Pine Island Sound-Estero Bay for a narrative of point-to-point paddles.