Good luck with finding hiking friends in the skeptics.
After TAM in 2008 I was hiking Whitney and some other peaks with ZERO others after trying to find other out-doorsy minded folk.
I generally prefer nights in or nights in the woods... but if we're going night out and I get $500 to blow, I'm spending it in Miami.
3:30 - Rifle range - $60 for ammo and range fees
5:30 - My house - Shower and change. Possibly sexy times.
7:00 - Sunset drinks at The Wet Lab - $30 (awesomely obscure oceanside bar)
8:15 - Dinner at Gigi - $55
(roasted pork buns, mushroom buns, grilled squash, honey bacon butter cornbread, PBR's)
10:00 - Coffee at Panther, short walk in the burgeoning art district - $13
11:15 - Fancy cocktails at the Delano Hotel's bar, in one of private poolside cabanas - $200
...probably more sexy times here
12:30 - Beers at Zeke's, and a walk down Lincoln Road. Awesome people watching there. - $35
1:30 - Buy a bottle of wine somewhere and walk down to the beach with it - $35
2:30 - Use leftover cash for a cab home, possibly some tacos on the ride back if there's enough there.