Key West: roosters, conch, and pie. Oh my!  

Key West, in many ways, is the Bahamas of the US. Just add former hippies nostalgic for the days of Woodstock and replace coconut drinks with Bloody Marys. Why is it similar? Well, the islands aren't that far apart, and Bahamians started visiting the area in the 18th century and became a big part of its population. The influence - all the way down to the references to conch (as in the shellfish and long time residents) - persists. You've never had conch? The shell is pretty. The actual fish? Eh...
Key West is not just another town in Florida. It is distinct, admittedly a touch weird, and has island vibes (read: laid back and taking in this thing called life) throughout. A small island that is easily traveled by bike (which I recommend because cabs are expensive for short distances and no uber/lyft) - activities range from museums to water sports. But fun fact: the reef nearby is dead so most of the sand is shipped in by dump trucks.
A great long weekend stay if you want some fun in the sun. Tiki bars, fried seafood, and perfect sunsets make it a favorite.
Best Entertainment
I wouldn't normally opt to see a drag show. No real reason, it just never occurred to me. The Adele and Beyoncé are eerily accurate and hilarious. Stock up on your ones.
Key West has a spectacular sunset and this is the best way to see it. Sunset plus endless hors d'oeuvres and wine - what more could you ask for? (PSA: Pace. Someone on our trip, who will remain nameless, overindulged which was really easy to do, and let's just say had an interesting remainder of the night.) Nonetheless, an amazing and classed up time.
Best Brunch 
You will never survive here if you have multiple Bloody Marys. Never. The vodka giveth and as always...taketh away. But hey, it's your vacation/life. Once you grab a drink and gage your level of risk aversion, settle in for delicious oversized pancakes, casual outdoor (garden style) seating, and live music.
Delicious southern food in a southern style home turned restaurant. Firefly also serves wonderful cocktails.
Best Key Lime Pie
You have to eat key lime pie while in key lime heaven. Seriously, I am not generally into pie, especially key lime pie, but it's really good. It's sort of like when people tell you don't say you don't like paella because you haven't had real paella. So true in this case.
Kermit's key lime is tangy and creamy. The lime is sharp but oh so good. And the store is super cute - there is a koi pond and garden in the seating area. Kermit's also has key lime flavored everything from cookies to bath and body products.
Also delicious but very different than Kermit. Key Lime Pie Co. is more contemporary - even the decor is modern and full of candy and ice cream displays. If you crave traditional desserts (i.e. sugar, butter, whip cream) this is likely more up your alley. Their coconut key lime pie is perfection.
Best Bar
I've never really been into rum (brown liquor does nothing for my personality) but this is a wonderful place. Located right on Duval street, it has a great rum selection and friendly staff. I also enjoyed the ambiance. The inside bar is bright and there's a patio, which for weather like this, is always welcome.
Other sites
Where Truman spent his winters. I'm more into Obama but the outside of the house was really cool. In fact, the whole community was a pretty part of the island and worth a visit.
A great plaza for people watching, cruise ship watching, and getting the Key West experience in all forms - in one spot.