I've attended the Champs Sport Bowl (also site of the Citrus Bowl) and Outback Bowl twice each in 2010 and 11 while I lived in St. Pete Beach, FL for a few years. The Outback Bowl is a great site for a game and they do a nice job. Very nice stadium and we scalped tickets for around 35 to 40 bucks. The teams stayed a few hotels down from my condo building and there are a lot of team events on the beach for fans to get involved in. There is ample parking right outside the stadium, shuttles from the most of the beach hotels, and it's in a nice area. The tailgating wasn't too bad either. The Citrus Bowl was a complete dump of a stadium, but now renovated. Tickets were cheap to scalp going around $25. The neighborhood is pretty bad, and parking, while ample, is had to navigate getting into and out of. Plenty of strip clubs and dive bars not far from the stadium for those looking for an adventure pregame. I wouldn't recommend heading out to the local pubs in the stadium area post game. It's probably in the worst area of Orlando.
If we wind up in the Gator Bowl, St. Augustine is an amazing city (the Historic District anyway) and is about an hour south of Jacksonville. They'll have the Nights of Lights going on which is beautiful during the bowl which I highly recommend. Its been rated a top ten most beautiful city during Christmas in the world. Lost of history, great museums, plenty to see, eat, drink, and the beach is a 10 min drive.
Amelia Island/Fernandina Beach is about an hour north of Jacksonville and is also a great area to stay with great beaches, history, etc.. Jacksonville itself is unimpressive, and the beaches are ok. I've never been to the Bowl as it was held on the 1st and I preferred the Outback so I can't speak to that.
I'm hoping for the Outback myself. If we do make it there and anyone needs recommendations on where to stay, eat, drink in the beach areas (45 min drive), I'd be happy to assist.