When we went to HHI we realllllly enjoyed One Hot Mama's (cheap & and very casual BBQ) and Truffles Cafe (nice, slightly upscale casual dining). We also liked Roastfish & Cornbread for the local flare (couldn't get Dye's to call us back even after leaving like 3 messages). Just OK for us was the Alligator Grille (had a coupon from Restaurants.com so that was a help since it was a tad pricey and the portions were small) and Guiseppe's Pizza (wished we'd tried the Mellow Mushroom for pizza instead). Both of these places were OK, really, they just didn't meet the expectations as we'd heard rave reviews for the pizza at Guiseppe's and who could get full on the tiny portions at the Alligator Grille (although the food was good there just wasn't ENOUGH of it). We did NOT like the Mexican place that was right there at the harbor across from the resort (within walking distance). Not sure of the name (San Miguel's maybe)? It was one step above awful for us. Nickel & dimed us for extra sour cream and looked at us like we had 2 heads when we asked for more tortilla chips etc. (Get a grip people - it's chips and sour cream not gold!!)
If we ever go back to HHI we would definitely go back to One Hot Mamas, Truffles Cafe and likely to Roastfish & Cornbread but would skip the others in favor of trying new places.