Key West trip thoughts?

If you want to be decadent, you certainly can be in Key West.

If you want to just bar-hop and people-watch and eat, you can certainly do that too. And enjoy it.

 

There ARE a lot of tourists faking it who make it less authentic. I love, love New Orleans, and I love Key West much more. But I'm a Florida beach boy, so it's more my speed.

And duh, po boy? Eat the seafood, dumbass.

And do NOT spend all your time on Duval Street. Go to the marina (specifically to Schooner Wharf for the music and Dante's for the fish tacos and the public pool). You guys are KILLING me with this thread.

 

Schooner Wharf is pretty cool. I still like the Duval vibe, especially if you get inside somewhere and watch it from the side.

 

Perhaps he goes to New Orleans for the conch chowder?

 

You had better have pronounced that ˈkɒŋk.

 

You grew up where?

Shee-yit, next thing, people are going to be explaining Bimini bread and Cuban sandwiches to me.

 

Hehe. I hear ya.

 

Even the Hawaiians don't like that shit.

 

If you're directing him down thataway, I've got to recommend the Southernmost Hotel. Best rates on the island (which still means you're paying $200 a night on a good night), plus free parking. It is a ways from Old Town, though, so if you've gotten a decent rate at the hotel the conference is at you might be better off there.

http://www.southernmostresorts.com/southernmost-hotel/

The Southernmost Hotel is on the quiet end of Duval Street, a block from the Southernmost marker. Roll out of bed and you're on your way. You will have to hike to get to the good stuff at the other end of Duval (it's a mile or two from one end to the other), but most of the fun is people watching anyway.
If you want to chill out for a bit, there's a pool with a tiki bar.

A couple other quick thoughts:
1) The beaches are generally shitty. They're all artificial, because the reefs keep sand from piling up. The beach at Fort Zachary Taylor State Park is pretty nice, though. Kind of tucked away and quiet. I'd recommend it for a quiet afternoon on the beach.

2) Unless you're in a time crunch, definitely fly into Miami or Fort Lauderdale and drive down. It's a 3-4 hour trip, but also one of the prettiest drives you'll ever go on. If you have an extra day or so, there's also a bunch of little side trips you can take in the Keys along the way.

3) It's touristy, but definitely go watch the sunset at Mallory Square. There's some amazing street performers. My favorite is this crazy sumbitch:



The angle of the picture is bad, but the guy in the green shirt is holding up a hula hoop. The guy in red is jumping through the hoop, OVER the woman on the bike, after getting a running start. Blows my mind every time I've seen it.

4) Prepare your "why did the chicken cross the road jokes" ahead of time. There are wild roosters everywhere. If you eat at some of the sidewalk cafes, they'll mill around under your feet and snap up any chunks of food that fall to the ground. It's so bizarre it's awesome.

5) If you're lucky enough to run into the Dirty Joke Man on Duval Street, give him a buck. You won't be sorry.

6) In getting back to the original question, hells yes a Key West trip is worth it. Expensive, yes, but worth every damn penny.

 

Key West itself left me cold, but I loved the Keys themselves. Bahia Honda State Park is one of the most wonderful places I've ever been to. Very nice beaches, interesting oddities, like the old railroad/highway bridge, etc.

And the drive down from Miami is a bucket list kind of thing.

 

I'll add to the group that says drive from Miami. It's great. As mentioned, with each passing mile it makes the anticipation grow and the worries go. Now that I'm older, I want to do it on my motorcycle. Don't blast the drive. There are plenty of places to hit along the way. Take your time and enjoy.