Just flew back from Tampa this morning. Stayed right across the street from the Convention center at the Marriott Waterside. Nice hotel with a very good lobby bar and outdoor patio bar on the water. Also a third floor pool bar.
There is a pretty good hockey bar called Hattrick's. If the Lightening are in town you should go - they play just a few blocks from the convention center. There is a free trolley (think St Charles Street Car) that goes from downtown to Ybor City. Lots of bars in Ybor. We had dinner at Columbia which is a very cool spot - FYI the bartender had three bottles of Pappy last night.
Went to Bern's and its a great experience. I thought the steak was ok (needed a lot more seasoning) but the atmosphere was fantastic. I could sit and drink in their bar all night. Think Goodfellas meets Casino. We were drinking with a local chick later and she said its looks like the inside of a whore house. Pretty spot on. Didn't know anything about the Dessert Room and the waiter didn't mention it - but we were drunk as fuck so he might have been trying to get us the hell out of the there.
Years ago we would go to Tampa and spend most of the time in Clearwater. That's a good spot. There is a crab place called Crabby Bills in St. Pete that was fun if you like to drink beer and pick boiled crabs.
Of course you have Mons Venus, and there is a Hard rock Casino near downtown.. I didn't go, but a few others went and they said it was fun. One of them won $800 so he was pretty happy.