Over on Sunday
We've been to FF four times and will be going again next year. You are correct, the official festivities end on Sunday 10/30, so no reason to hang around until Tuesday unless you just want to rest, recover and chill (which is GREAT to do in Key West anytime!). But it will be quiet as of the end of Sunday, nothing going on Monday. The island settles back down to recover.
We've done a few of the official events, such as the parties hosted by the bars or whatever. We try to make it to Dantes pool party, we've done the pink party, always make sure we hit the masquerade march Thursday afternoon. But to be honest we never stay at the parties for long, its just an excuse for a themed costume and something to aim for, but the real way to do it (as another suggested on here) is to just float around Duval St and let it happen. The best thing about FF is serendipity - you just never know when you will stumble into a great bar, great crowd, great band, whatever. But I guarantee you will!
See if you can get your wife to dress up, its more fun if you participate, and it doesnt have to be naked or risque, nobody judges and its just fun. The people watching in the Fantasy Zone (corner at Sloppy Joes and extending towards Capt Tonys) is always a wild scene. Enjoy!
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