Pre-Dominiom war when everything is pretty chill. Starfleet kinda seems fun until you realize that you have to basically do military training and all this bullshit to join and then you gotta go die in space half the time. I'd maybe just try and get a runabout or the equivalent and just sorta wander around with some pals and look at totally safe and previously explored space things. I would also open a Volcel Precinct on Risa.
Open a speakeasy that gives bathtub gin to Federation seamen (commissioned officers have to barter) while they're in dock above Earth. Just drinking synthehol has to get old. We'd have watchwords and shit to make it fun.