Depending on the time of year, going to watch the sunset from Mallory Square is a good way to start the evening. The sunsets will be better if there are clouds. When we went in 2011, there were no clouds so the sunset was a bit boring and there was no green flash either.
Sunset Celebration occurs every night at sundown on the piers at Mallory Square. There are street performers, music, vendors, and cocktails. You have to see the cat guy. You will know what I mean when you go there. There are a lot of families there and it was nice. Recommended for everyone.
Life in the Keys must be good for you! They were in a photo from 1970 in the East Martello Museum, in a local 'whats happening magazine', The Key Wester, and on the pier that night! How do they manage??? They haven't changed a bit.
Dress Code: Come as you are...
We had a Key Lime Margarita here, while waiting for our sunset cruise.
There are numerous bars just like it along the waterfront.