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That's hard to say without knowing the route you're taking. You could head straight down to Naples and cut across but that would put the halfway point somewhere in the middle of the Big Cypress National Preserve. The most direct route cuts through Belle Glade, but there's a whole lot of nothing until you get to Andytown, which hardly qualifies as a city. Your best bet is to take the Turnpike to Route 1, which puts the halfway point at Deerfield Beach, but Boca Raton and Pompano Beach are within the margin of error.

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