Taking a trip with my mom and brother to Key West this February. We are staying at Parrot Key Resort. My brother loves to fish and would like to go deep sea fishing. Wondering if we should rent our own boat or go with a tour. Thoughts? Also, any other recommendations for the trip? It's kind of a "cancer break" trip for us as my brother has been diagnosed with stage 4 prostate cancer and just wants to get away from it all.

Thoughts and Prayers with you all. I would suggest a chartered fishing trip. If you want to try a really good Italian Rest, just a bit off the Duval area, try Manga Manga, we loved it when we were there a few years ago.

I'd say the Little White House & Hemingway house are both worth taking tours of.

Yes rent a boat if you can and feel comfortable in doing so.

Many diff food choices, Louie's Backyard and Blue Heaven are two favs.
Do a search here for Beerman and key west march 2014 for his well researched and written trip report.