Except we forgot about the "winning money" portion of the agenda and instead just had fun.
On our first night, we walked to our favorite truckstop/Denny's/motel/casino - the Wild Wild West.

source
Andy: So, Elmo, Marilyn Monroe and Elvis Presley at a bus stop . . .
Rachel, Kara and I, waiting for the rest of the joke: And . . ?
Andy: No, right there. There's 3 people dressed like that waiting for the bus.
Sure enough, we turn are heads and see these 3 characters on the bench at the stop.
Only in Vegas.
Night number two brought our adventure all over the strip and included a visit to an off strip microbrewery. It was here that Andy maybe had a beer too many and we walked off to the next bar.
Kara: We should call Kerri. (pulls out phone)
Andy: YEAH! PHONE BOMB!! (pulls out his phone)
Nagging wife a.k.a. me who is worried about tipsy Andy breaking his expensive phone: Honey, put your phone away, we'll just use Kara's.
Andy: PUT YOUR FACE AWAY!
The next bar we were walking to happend to be a pub that had a 7 second challenge.

source
Atop the bar were hourglasses, all timed to 7 seconds. You were allowed to order the beer of your choosing and if you could chug a full pint in under 7 seconds, your drink was free.
Andy: Guinness please.
Bartender: And ready, set, go. (turns hourglass)
Roughly 5 seconds later Andy set his glass down, victorious.
Bartender: Good job, man.
Andy: I feel like I was cheating. That was like drinking milk.
The rest of our visit was a bit tamer and we ended coming home within our budget. Including the time we spent at the airport after a lengthy flight delay during which Andy found the Star Wars slot machines and lost more money.