Exile Island? Funky Home to All Kinds of Characters? Cruise Ship Day Stop? All of these and more that is Key West. Spent three days there and here's my opinion, for what it's worth.
People jam Duval Street, heading for Sloppy Joes' or Margaritaville, but places locals head to like Salsa Loca are mich more fun.
Shops have it all, even things you never knew you wanted or needed. Or could afford in come cases.
Street Performers at Mallory Square are free and very good at sunset.
Hemingway House is a nice tour. and lots of six toed cats too.
Some restaurants are very humnble, others very fancy, but food overall is excellent. Try Cafe Marquesa, absolutely outstanding! Or the Grande Cafe.
Parking enforcement is all day long till midnight so avoid driving if you can.
The Trolley sightseeing bus is excellent for getting around in daylight -- two days cost about $58 for two people, less than two parking citations
Be aware that people get pretty happy after midnight, bars close at 4 am.
You have "Nailed it", this is a place for "Buddies" to go, not families, and maybe not couples. But I don't stay out after midnight, (Except, like the movie, in Paris), so I don't know what goes on till 4 AM.
There does not seem to be a "Recession" there! I should have recommended earlier a stay at the CY, they always upgraded me to a 2 room suite, but that was last year, who knows these days?
Your pictures looked great.
That would be rediculous to accept that offer.
I enjoyed my stay at the FF, and at the Cy, but that was with guys, and we could have cared less about something special. Now my wife, no way, but I have never taken her to KW, because she would think I have lost it, not her kind of place.
Save those points for something really special. If you would see how they treat me on just points in London/Paris, why would I waste them in Key West.
Have a good trip!
By the way, I have not been to the places you recommended, and thanks, they sound wonderful.
Also the Roof Top--an expense account kind of place but wonderful views and fantastic sea food, We used only 50K points at the FF, which translated to paying nearly 600 dollars in cash if we'd paid for the room. A good points bargain I would say since the Marquis is 40K a night for a 700 dollar room.