+1 on Columbia. World class Cuban food. Everything's good, but if you can't decide, check out the sampler platter. It's a little bit of this and that. Tampa Bay brew company in Ybor city has good brewpub beer and a gastropub menu. Diners, drive-ins and dives has been there. Ybor has a bunch of other restaurants but it isn't close to CCB, which is closer to TB stadium and the airport.
In orlando, check out downtown. Tons of places down there. There's a few good bottle shops. Check out Total Wine and Knightly Spirits. Link to downtown: http://www.downtownorlando.com/life/dining