"Key West - Great Restaurants & Water... " a Key West Travel Page by FatesWarn

Before my first visit to Key West, I did a lot of research on the restaurants. My husband and I are usually pretty health conscious, so when we go on vacation, we like to let our tastebuds go on vacation as well. We don't want to waste any of our dining experiences on so-so meals. I continue to do this for each trip, and will sometimes return to the same places if they were good enough, but overall, we haven't had any BAD dining experiences there.
If you're on a budget and eat nowhere else, you MUST go to Sloppy Joes for a Sloppy Joe, and to B.O.'s Fishwagon. You'll be able to eat cheap without cheating your tastebuds.
If you're a breakfast person, do not miss Camille's. They have daily specials, so you could eat there every day if you want.

Sunset cruises and kayaking trips are a lot of fun. I recommend choosing a small charter (usually holds around 6 people), and booking a semi-private trip. You might get lucky and be the only people on the trip, but you only pay the semi-private price. If not, you only have to share the boat with 4 other people, which is much better than the numerous amount of people on the larger charters. It's good to keep your options open when booking the small charters, though, because sometimes they cancel on you.
For Kayaking, I highly recommend JavaCat Charters. The JavaCat is captained by Carla Bellenger. Her boating expertise is excellent, and she's also great fun to have with you for the day.

I see a lot of families vacationing in Key West, but I would recommend to use caution in choosing vacation dates when you're bringing children to Key West. There are a lot of festivals that would probably be considered inappropriate for your children, as well as the Spring Break season. Outside of those times, just be aware that Key West is a very open town, and what is perfectly acceptable to some, may not be for you. Keeping that in mind, be sure to ask your hotel staff or inn-keeper about sticking to family friendly areas.
There are a lot of museums, which are really pricey (average $15 for one adult), but they are probably good places to take kids and keep them occupied. Pat Croce's Pirate Museum was pretty cool, but I thought the rest of them were not worth their price.
I do recommend forking over the fee for the Lighthouse Museum, though. The view at the top of the lighthouse is incredible.