Mallory Pier at sunset is home to a number of street performer shows. There is a man with trained cats, a fire breather, a number of trained dogs, and lots of handicraft sellers. It is a fun place to catch what are generally family friendly street performer shows and see a beautiful sunset. Many of the adults are drinking so you will have to keep a good eye on toddlers running around because people won't be watching for them underfoot. That being said we took our 20 month old down there three times on our visit and he liked it a lot, especially the cat shows and the spiderman.
This is a place I would not take the kids in the evening. There are a lot of people that come out to do "tricks" in order to get tips. There is a nice restaurant on a dock where you could watch the sun go down on while enjoying pretty good food.
Great with little children. It is a Key West traditions, nightly. There are clowns, mimes, jugglers, artists, dogs doing tricks, food vendors...unicycles...you get the picture. It is crowded and hard to park in the area around sunset so go early or walk if you can. We have some very funny video our kids with the mime called "Silverman" and we just saw it recently. Brought back very happy memories. It is a tourist experience unique to Key West. At least go once!