Church Street - Chillers/Big Belly Brewery/Latitudes is a great spot, the first couple of floors are just OK, but the rooftop bar is a great place to hang out. I also like the German bar right next to it (Schumann's). Orlando City Soccer Club has a bar on the other side of the RR tracks called Lion's Pride. You have a couple of burger spot/bars on either side of the tracks, Graffiti Junktion has an outdoor plaza, and the fans who enjoy LGBTQ entertainment can go to Hamburger Mary's.
If you then head north on Orange Avenue, there are a bunch of spots (including on the side streets) - Chela Tequila & Tacos and Corona Cigar Company are both in a one-block development at the corner of Church & Orange. Across Pine Street from Corona is a speakeasy called Hanson's Shoe Repair. On Orange, between Pine & Central, you have 3 gastropubs, Orlando PourHouse, The Underground Public House, and Avenue Gastrobar (there's a fourth one 2 blocks north called Finnhenry's). At Pine, you have Tanqueray's (in the basement) and on Central you have Ember.
Wall Street - another block north and you have a whole block to the east of Orange Avenue that is not open to traffic and is all bars. For a lot of big events, bowl games, etc., this becomes a big party area.
Farther north - the two blocks between Wall and Jefferson have a bunch of older bars, but some have been renovated recently, including Orange County Brewers.
There are a bunch of other spots within 2 blocks to the east or 2 blocks to the west of Orange Avenue. So about 10 blocks from north-to-south and about 4 blocks to either side of Orange Avenue, you should have plenty of options.
