Spring Break in Naples
Randy's Seafood - casual (long waits but soooo worth it) awesome oysters - http://www.randysfishmarketrestaurant.com/
Wylds Cafe - awesome awesome upscale - http://www.wyldscafe.com/
Cilantro Tamali - small family owned mexican chain - heard great things about Iguana Mia too but haven't gone.
I love Bonefish Grill too (chain but awesome) - http://www.bonefishgrill.com/home.asp
I like Tommy Bahamas, even though it's a chain and branded. The food is good and islandy, and you can't help but relax to the live music and warm breezes. Great pulled pork sandwich.
For the best key lime EVER in your life, go to Bella Maria on Fifth Avenue. You might need to call ahead to get her to make a key lime tart for you. It's just beyond... I have no words. Buy the whole big thing and eat it for breakfast, lunch and dinner. Yum. Instant vacation feeling.
Seconding Randy's Fishmarket. Everyone raves about it. I'm not a seafood eater, but my finicky mother said the coconut shrimp was the best she's ever had. And she's had a lot.
For a hometown feel, Gatsby's Pizza is excellent. It's in a nondescript strip mall behind the Walgreens at 41 and Wiggins Pass, so almost in Bonita Springs. But it's owned by a family from Columbus, Ohio, so it's filled with Buckeye paraphrenalia and the folks are fun. The pizza is thin crust and covered with spicy pepperoni, if you like. Yum. Our favorite.
For burgers and fries hit Cheeburger Cheeburger on 41. Burgers in all sizes up to two pounds! Fries fried in peanut oil- yum, but use moderation or you'll feel it later. Best chocolate shake you'll ever have. Even if you don't like burgers and fries, go for the chocolate shake.