Hit the Clevelander Bar, 1020 Ocean Dr. on the beach for Monday night football, you'll enjoy it. Sad part is most that is topless on the beach, you really don't want to see.....
Stayed there at the hotel for a few nights back in the late 90's, it was an absolute blast in a retro art-deco sorta way...Creaky old elevator, funky old kidney shaped pool on the side with the obligatory pool bar, beach right across the street, great place to be when winter sets in back here in the real world...
Yep, my personal favorite on South Beach. I used to spend a lot of time down there back in my hay days consulting, kept my fishing boat at Haulover and one of my best buddies has a place in North Miami beach right on the beach that I would stay at when in town to fish. Great place to get away to have fun!
Place had a European youth hostel feel to it, I can't swear I was the only guest from North America there, but it felt that way at times...
The Gansevoort is nice you wont be disappointed. Plus its at the North End of the beach on Collins Ave so when you are driving or taking a cab you wont have to battle with the insane traffic on the South part of Collins. Take your girl to Lincoln Road she can walk around and check out the shops and make reservations at my friends restaurant called the Meat Market http://www.meatmarketmiami.com/enter.html one of the best restaurants in Miami.
At the Lincoln Road outside mall, don't be alarmed at all the fags holding hands, might even get lucky to see some hot lesbo's tounging eachother! You might want to check out Pacific Time on Lincoln Road too, great but pricey place to eat!
Stayed here last year. http://www.standardhotels.com/miami/ You'll need to take a cab to get to beach, but the hotel was very cool. Each room feels like it's own private bungalow.
The Victor is pretty cool. 2nd floor infinity pool that overlooks Ocean Drive. http://hotelvictorsouthbeach.com/ The Tides is nice too. http://www.tidessouthbeach.com/ Even if you don't stay at the tides, great food and drinks, and an awesome place to lay on the couches out front and people watch. But there's an eyeful anywhere you go.