Potential answers for "Traveling hobo-style"

⭐⭐⭐⭐ HOPPINGAFREIGHT
⭐⭐⭐ BOHOCHIC
⭐⭐ RIDETHERAILS
⭐⭐ TATTERS
⭐⭐ STEADYWORK
⭐⭐ SWAGMAN
⭐⭐ RAILS
⭐⭐ VAGABOND
⭐⭐ KINGOFTHEROAD
⭐⭐ TRAMP

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Border of a table   Emotionally cool   Puerto Rico or Maui