The Gulf meets the Everglades at the start of the Florida Keys Overseas Paddling Trail in Key Largo. While paddling past the fossilized coral reefs that comprise the Keys, you'll see critters like rays, manatees, sea turtles, and dolphins. On Big Pine Key, visit the Blue Hole and keep a lookout for Key deer, a diminutive (and endangered) subspecies of whitetail. The trail ends in Key West, where the wildlife is typically either inebriated or descended from a six-toed cat given to the town's most famous resident, writer Ernest Hemingway. — Katie McKy
See more: NORTH AMERICA’S BEST PADDLING TOWNS.
This story will appear in the June 2015 issue of Canoe & Kayak.