DeLand/ Winter Park
First, Stetson is a far better place for a real college education with real people than Rollins unless you are just looking for a country club (with a chip on its shoulder that it is not in New England) and not a college where people are there to learn.
Cress-- fine dining. Higher aspirations than any other restaurant in town and usually attains them. Expensive and generally worth it.
Norville Barnes -- good steaks and other similar fair. But expensive (more than it seems to need to be) and the burlesque decor is a bit off putting for families. The same owner's Abbey across the street is the place for unique beers and the Stetson intellectuals (and faculty bands), but also quite expensive. The happening place for Stetson people these days is the newly reopend DaVincis (but no food there).
Penachos -- the real thing in Mexican food. I actually like this one the best of all because it is authentic, but dont expect it to be like lame chain Mex places. Very inexpensive.
Everything else is OK, not great. Odums=ok Thai, Wasabi=ok Japanese, DeLand Fish House=sort of ok fried fish, Bill & Franks Brick House = ok BBQ (have the pulled pork & sweet potatos). Nobody seems to know how do make memorable BBQ in Florida. But the sweet potatos are amazing.
DeLand is a funky cool place if you look around. Much more interesting than the overbuilt and commoditized Winter Park. But if you want life to be like a magazine ad it may not be the place for you.
Deland also has some hidden gems. If you truly want to experience deland's local fare you might want to head west on 44 til you get to the saint johns river. On the banks is the best little catfish joint in Volusia county called the shady oaks fish camp. Homade potato salad, hush puppies and whole catfish fingerlings dipped in seasoned cornmeal and fried crisp. A real hole in the wall but good. If you dont feel so daring you can head back to deland and go to emy's time out tavern. This is a nice little hole in the wall german place that serves homemade german food. Emy is from germany and she might be performing her german music if you are there on the right sunday. Homemade bread , steaks, pickle salads and great steaks! Mexican is the other popular ethnic food in deland and my favorite is El Rancho at the corner of hwy 17 and hwy 92. This place is owned by a mexican family that serves all the mexican classics as well as grilled steaks and fried whole talapia. Very good!! If you don't want to spend money and want to pick nic,,there are a killer taco truck south of the corner of 44 and truckroute.
If ALL this sounds too wild,,just walk across the street from stetson to the Original Holiday house. This is your grandmas favorite place to eat. Carved roast beef turkey or ham with a huge salad bar. Imagine thanksgiving or christmas dinner any time you want it.