Welcome to Chokoloskee
Home of hard stories, soft sunsets, and the best kind of trouble.
Chokoloskee is a small island at the very edge of the Everglades, connected to Everglades City by a short bridge and surrounded by quiet water and backcountry routes. Though tiny in size, it has one of the richest stories in Southwest Florida. Early settlers built a remote frontier community here long before roads reached the region, giving the island a rugged heritage that still shapes its character today.
At the center of that story is the historic Smallwood Store, a 1906 trading post that served as a lifeline for families, fishermen, and travelers navigating the Ten Thousand Islands. Local folklore about plume hunters, smugglers, and the notorious Edgar J. Watson adds a layer of mystery that visitors still find fascinating.
Today, Chokoloskee is peaceful, welcoming, and known for its exceptional fishing and quiet, laid-back charm.
Explore the Outdoors
No matter where you stay in the region, you’re only minutes from amazing ways to experience the Everglades & the Ten Thousand Islands.










