1. Good places to stay?
Downtown Tampa: Hilton, JW Marriot, Hyatt, Aloft Tampa Downtown, Sheraton Hotel
Close to Stadium: Aloft Tampa Midtown, AC Hotel by Marriot, any of the hotels near the Airport
Close to nightlife: See downtown tampa above, Epicurean Hotel,
2. Good Cuban food?
Columbia in Ybor, Le Segunda Bakery, La Terisita, West Tampa Sandwich Shop
3. Best beach?
For partying and a younger crowd, St. Pete Beach (near Post Card Inn)
For a family oriented touristy experience, Clearwater Beach
For a quiet not as crowded experience, Indian Rocks, Sand Key
4. Nightlife? (I'm 21)
Most the college kids go to Soho (South Howard). There are about 10 bars within a mile of each other. Some of the most popular are Bar Howard, Macdintons, Soho Saloon, and Yard of Ale
If you're into line dancing and country music, check out Dallas Bull
If youre into a more young professional crowd (college kids still go here), check out downtown tampa (Parks and Rec, Gen-x, American Social, etc.)
5. How is the tailgating and where do I park?
Tailgating is probably a $&#@show if you havent been before. The two main things are that (1) if you want to park with friends or family, you have to drive in together because they won't allow you to save spots and (2) you need to buy your parking in advance (you can do this on Raymond James Stadium's website)..
Lot 4 (on the north side of the stadium) usually has a younger crowd, as thats the side the student section is on. Most of the fraternities rent out houses or lots to tailgate out of in the area, so although you may see one or two fraternity tailgates at the stadium, the majority will not be at the stadium.
Lot 6 (on the south side of the stadium) is usually more family oriented. That is also the side on which they usually have "Bulls Bay" set up which I am not sure if they do anymore.
6. Flags allowed in?
They will let you in with a flag but if one of the sentry security guards (aka glorified mall cops) decide they don't like it, they will kick you out (I got kicked out during last year's USF-UCF game because I had a trump flag)