Another vote for the 650 V-strom, the KLR650, or my favorite 650-class dual sport bike, the Suzuki DR650. Any one of these will allow you to ride places you would never think of taking a Harley.

I recommend against cruisers of any make, because the feet-forward riding position does not afford good control of the bike, and makes it difficult, if not impossible, to stand on the pegs when encountering an obstacle.

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Not in jail.