Well, we wanted to do Hawaii for our 20th, but finances…not so much. I asked Ivylad if he wanted to spend a week in St. Augustine or Key West…no contest. And me, tightwad that I am, I’m not going to worry about the finances. We’ve reserved the room, we’re saving up the money, and we are going to have a fabulous time!
I’m bookmarking this thread too for my own purposes.
I live in Key Largo (at the top of the island chain) and have been to KW many times. Feel free to PM any specific questions you may have. One “don’t miss it” for me is Irish Kevins, you have to see Jon Solinsky.
http://www.irishkevins.com/home.htm
He’s a fantastic musician/comedian and you’ll have a blast. Tip him well 
Everyone else has covered a lot of ground with recommendations. I would be sure to book a snorkel trip if you like the water, and maybe a day trip to the Dry Tortugas.
There are nice beaches in Key West and just north (if you have a car) at Bahia Honda State Park. There are no beaches in Key LARGO, a mistake a lot of people make. We have a huge, thick coral reef system off of our shores, but no big sandy beaches. Key West has reef as well, but also has some nice, sandy beaches to enjoy.
Here is some beach info:
http://www.keystravel.com/Beaches.html
The thing about our beaches is that you don’t get those huge, rolling waves like you do in a mainland shore- the coral reef system makes it so that the waves don’t roll in that way and much of our water looks more like a lake than an ocean. I’ve been miles out on the water and have seen the water so calm that you could skip stones on it.
Oh, one thing I recommend is getting an insulated refillable drink container from Fat Tuesday’s on Duval. They fill it with a booze slushie (not very strong, very very refreshing) with refills for $7 (the first fill with insulated cup is $10). Well worth it to refill whenever you stroll by there, IMHO and you can use it day after day.
About the hotel:
Their website says they have a shuttle, so I guess they have a shuttle now! Honestly, we just drove everywhere when we were there so they might have had it then too. They have an awesome pool. We’d chill there during the heat of the day, the hot tub was nice at night too. The hotel itself is oceanfront. It’s the ocean, N. Roosevelt, and then you’re hotel - no beach or anything, which was kind of odd for us when we got there.
About beaches in KW:
Well, it’s not your typical beach like someone else said. There is a nice piece of beach (Oh - Smather’s Beach well it’s been the last times we went 2005/06) on the Atlantic Ocean side along South Roosevelt Blvd. I think it’s west of the airport, there’s on street parking and sometimes some street vendors there. A word of caution and I don’t know if it’s still the same situation, but the bathrooms are very open. I guess due to the transient population and the tendency for it to be a ‘hook up’ spot, there are no doors, but it’s semi-private, but still it was a bit awkward at first. You might even catch the some jets flying over doing their morning practice sessions from the nearby bases.
There was another place they tried to call the beach, I think at the southernmost point - but that was a waste of time. Stinky too.
it’s been years since i’ve been. my husband’s a conch. i do recommend the mel fisher museum. we went out on a glass bottom catamaran that was pretty cool. when i was there, the aquarium was very old but charming. my husband said it hadn’t changed since he was a kid in the fifties. we also took a ghost tour that was pretty cool, if you’re into that kind of thing (we are). there is an old museum–i’ll have to look up the name for you–that houses a haunted doll named “robert”.
be back with more info!
ok–it’s the east martello museum & gallery. a good place for steaks is martha’s steak and seafood. i always use tripadvisor.com when planning trips; you might want to check that site out. hope this helps–have a blast!!
Just a follow-up post to say that we’re here! We arrived last night, and promptly stumbled across a bartender who used to work in the town next to where we live (and who knows our regular bartender). Small world. 
We went downtown last night but didn’t venture very far or into Old Town; today, however, we were all over! It’s neat to see all of these places that you guys mentioned.
We went to Bahama Village and checked out Goombay, the street fair that starts Fantasy Fest. That was pretty cool, and I had my very first arepa (corn cakes with a cheese center). So yummy! We also went to the aquarium and got the tour/saw them feed the sharks, and I got to pet a nurse shark. We did a lot of walking – so much that my old sandals gave me a blister, and I stopped and bought new ones! I also got a t-shirt from the Hard Rock, because I have Hard Rock shirts from every city I go to that has one. We didn’t eat there, though: Hard Rocks are cool to look at, but I’ve always found the food to be mediocre and overpriced. We ate lunch at the hotel tiki bar, and had dinner at the Conch Republic Seafood Company. Right now we’re back in the hotel for some downtime, but will head back downtown in 1/2 hour or so in search of a new bar. I might suggest Irish Kevin’s to my SO.
We picked up a few charter handouts: we’re interested in a dolphin watch/snorkel trip, and a day sail on a “pirate” ship (the handout says we get to fire the cannons!). We’d also like to go on a sunset sail one evening. Good thing we’re here until Wednesday. grin Tomorrow we’ll be at The Sports Page (new bar, just opened in May) pretty much all day for the OSU game. We wound up there last night, and discovered that the owner is from Ohio and they get a decent OSU crowd! He recommended arriving early for a seat, so we figure we’ll get there around 12:30, have lunch, watch the 3:30 game, then go somewhere else downtown for dinner. We have no plan for after that.
Oh, sounds like you’re having fun! I think I forgot to mention the Pirate museum:
That’s a neat place and I love the restaurant nearby, The Rum Barrel
http://www.piratesoul.com/rumbarrel/
You can get a whole roasted turkey leg. ARRR Matey!
Fantasy fest is more than a day. The parade is the last Saturday before Holloween. But the week of includes the pet costume contest at the Casa. The pretender in Paradise which is an international costume contest which is big fun. The day after the fest ,everybody is gone. That is when you go eat and drink. There are all kinds of great restaurants . Our condo is next door to Louies Backyard. Just south of that is a Shulas steak House. There is always things to do. On Duval about 5 blocks from the Ocean is a French Restaurant that has great breakfasts. There are good Italian .French and Cuban restaurants. On Stock Island there is a good bar that also sells fresh caught shrimp and fish int he back. They have a good fish sandwich there too, the Copper Nail I think. Forget golf .It is a150 or so to play. If you take a fishing boat out ,restaurants will fix it for you. They get to keep whats left though.
We might just have to check that out, thanks!
Yes, that’s why I said that Goombay is the street fair that starts Fantasy Fest. Goombay itself is two days, yesterday and today from noon-midnight. We might have to go back tonight so I can get another arepa. grin
We were interested in that, but we leave Wednesday around noon and it’s Wednesday night.
That’s when we’ll have been back home for 3-4 days. 
South Beach is a lot different from the Keys, but it is great for people watching. If you hit the town on South Beach, you’ll find yourself surrounded by appearances of wealth and ostentatiousness - Trust fund babies who spend all day at the beach and the gym, then sport around town at night in their ferrari’s.
My recommendation is to not take it too seriously, but just enjoy gawking at the pretentious and pretty people. And keep an eye out for a random celebrity entourage.
We went on the day cruise to the Dry Tortugas, and it was interesting, but… do take pre-emptive dramamine if you do it. I got violently seasick for the first and only time in my life on that cruise and it harmed my enjoyment of it. Also, do wear sunscreen and bring a hat, because you will likely spend most of that several hour cruise out on the deck. My husband forgot to put sunscreen on his feet, and it was bad.
On our drive up the Keys, we found Harry Harris Park which is a manmade lagoon. It was not crowded at all, being off the beaten path. We also saw wild iguanas roaming around there. Worth checking out.
A good restaurant to try is Michael’s, if you like fondue. It was affordable and delicious, in a nice setting (thought if you order fondue they make you sit at the bar).
Second the butterfly museum and Hemingway House as sights to see.
Wow. Just, wow. Weird doesn’t even begin to describe it.