YES!!!! What do I win???
Here's an old thread I posted on about KW:
http://forum.slowtwitch.com/...=key%20west;#1046366 You can fly straight to KW or in to Miami. It's about a 3hr drive to KW from Miami depending on traffic. I personally love the drive and enjoy all the weirdness on the way down. Some people finding it very tedious and boring. It can be slow going since it's just 2 lanes in each direction, but I think it's worth driving. There are some interesting things on the way down if you want more of the local flavor. However, if you fly into KW, you can probably just cab it to the hotel and walk the rest of the time.
Let me know if that's what you decide to do. I will have quite a few places you should stop on the way down.
For accommodations, you might want to check a place called the Artist's house (
http://www.artisthousekeywest.com/rooms.htm). My folks stayed there and really liked it. It's supposedly haunted - if that doesn't bother you. Most of the action is on Duval Street, so I'd suggest being semi close to there if you plan to go pub crawling. Also, Smathers Beach is the public beach on Key West. It's not that great (compared to other FL beaches), but then KW doesn't have any natural beaches. Most of the resorts and big hotels have their own private, man-made beaches. So, if that is important to you, look into staying at a hotel. However, most places have pools and there are zillions of options for boating, snorkeling, scuba, etc.
I've also stayed at the Southernmost Hotel:
http://www.southernmostresorts.com/ And you've got to do the Ghost Tour. It's my favorite thing in KW. It's a neat way to learn a little of the history while creeping yourself out. And the history is super interesting: pirates, bootleggers, voodoo, santeria, rumrunners, outlaws, outcasts, vigilante justice, and eccentrics. The tour leaves from the La Concha Hotel on Duval Street, which I think is expensive but might have some special rates:
http://www.laconchakeywest.com/.
ghost tour:
http://www.hauntedtours.com/ You also will want to do some boat/fishing/diving/snorkeling for sure.
food:
http://www.colespeace.com/ --> artisan bakery
http://blueheavenkw.homestead.com/...aurant_Key_West.html bars:
http://www.capttonyssaloon.com/ http://www.sloppyjoes.com/ 'workouts:'
http://www.geocities.com/keywesthash/ --> if you want to hash
http://www.southernmostrunners.com/ --> for all things running related in the lower keys