We had a blast walking Duval window shopping and people watching a few times. There are many bars and restaurants to suit anyone's needs as well as shopping from local trinkets to coach and express.
There are some homeless folks and various street type performers vying for a $1.
You can generally get away with walking around cocktail in hand as long as its in a solo cup. Keep in mind it is still officially illegal-- not an open container city.
Many of the bars/ restaurants have music you can hear from the street if you want to stand and listen without going in. A few places tend to attract crowds out front like sloppy joes, Irish Kevin's, margaritaville, coyote ugly and Fat Tuesday to name a few.
If in key west, you have to walk Duval!
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