Chokoloskee, FL

Chokoloskee sits right at the southern tip of Florida's Ten Thousand Islands, connected to neighboring Everglades City by a single short causeway. Life here is slow, quiet, and completely tied to the water. Long before roads reached the island, locals relied on boats for everything from groceries to mail, and that secluded, frontier feel never really left. Today, it attracts avid anglers, paddlers, and people looking for a peaceful coastal hideaway surrounded by endless mangrove channels and national park waters.

ATTRolekinderhook / CC BY 3.0

The community's history is on full display at the Smallwood Store, a rustic trading post built on wooden stilts over the water in the early 1900s. While the building now serves as a local museum and boat tour launch, it still anchors the island. Living in Chokoloskee means easy mornings on the boat ramp, tight-knit neighbors at the marina, and direct access to some of the best backcountry fishing in the country.