See our whole list of best summer paddle trips.

• Distance: 43.5 miles
• Time: 2 days

Blue-haired snowbirds aren’t the only ones flocking to south Florida in winter: The dry season’s warm, lower-humidity conditions also attract actual birds by the thousands. And dropping water levels concentrate freshwater alligators in the remaining waterholes, making winter prime time for a wildlife-spotting expedition. Find the best option in the Everglades’ Ten Thousand Islands area on this 43.5-mile, five-day loop linking inland swamps and gulf beaches.

From Everglades City, paddle 9 miles southeast and up the Lopez River to Crooked Creek Chickee, a covered tent platform hovering over the water on stilts. Day two, hop on the inland Wilderness Waterway, a 99-mile route through mangrove swamps, open bays, and sawgrass prairie connected by wide rivers and narrow forest tunnels. Follow it 10 miles to Sweetwater Bay Chickee, near a freshwater zone where gators bask on sunny streambanks. Then paddle the Chatham River to Pavilion Key (11.5 miles; time your trip to match the outgoing tide), then Rabbit Key (another 4 miles), both white-sand beach sites on the Gulf of Mexico where chances for glimpsing white pelicans, bald eagles, and dolphins are high. You might also see sea turtles and manatees in the grasses off Rabbit Key, especially closer to spring. Head back to Everglades City via Chokoloskee Pass on an incoming tide.

One animal sighting you don’t want: raccoons raiding your dinner. Store food in a kayak compartment or hard-sided cooler.

Average January high/low 78°F/54°F Dry season December to April Permit Pick up at Gulf Coast Visitor Center; $15 plus $2/person/day Kayak rentals