July 14, 2026
Lake Osceola, Winter Park: The Boat Tour That Outlasted Everything Else in Orlando
The narrow canals between Winter Park's lakes were dug for Gilded Age homeowners — and in 1938 they became the route for an attraction that has run longer than anything else in greater Orlando
Since 1938, a pontoon boat has been pulling away from a dock on Lake Osceola and threading into a canal barely wide enough to pass another vessel. That tour — the Winter Park Scenic Boat Tour — has run continuously ever since, which makes it the oldest continuously operating attraction in the Orlando area. Theme parks opened around it in the decades after, and the boat kept making its hour-long loop.
The route runs from Lake Osceola through canals to Lake Virginia and Lake Maitland — passages narrow enough that the trees on either bank close in overhead. The canals were dug to connect the lakes for the resort community that the town's founders had in mind from the start.
That ambition goes back to 1881, when New England businessmen Loring Chase and Oliver Chapman bought land around Lake Osceola. They were laying out a resort community of grand homes, gardens, and tree-lined streets, and the lakes were the centerpiece. Connect them with canals and a chain of separate ponds becomes a single navigable system — water to move across and build along. The canals were the infrastructure of a planned community, and they are what makes an hour-long tour through three lakes possible.
The banks along these passages grew a canopy of cypress and oak, and the backs of the lakefront estates line the water.
In 1858, David Mizell Jr. and his family became the first settlers, homesteading near Lakes Virginia, Mizell, and Berry. The settlement that grew around the Mizell plot was called Lake View. In 1870 it got a post office and a new name: Osceola. The town that the name once belonged to became Winter Park when Chase and Chapman drew up their resort. The lake still carries it.
The lake itself is shallow, working water. It holds largemouth bass, bluegill, black crappie, and channel catfish — the standard Central Florida mix. Anglers fish it with live bait and lures that imitate small fish or insects. The boat tour passes over all of that on its way through the canals.
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