Keywest Trip Ideas & Tips

Trip details... flying into where? How long do you have?

Key West is a great place to buy an overpriced drink or burger while sitting elbowtoasshole with the rest of the tourist population. I highly recommend trying it once. The place is small enough to walk if you're in shape... I personally have a better time wandering back into the residential neighborhoods and finding the local bars. You can only enjoy the history of a musty smelling historic bar for so long, and I'm too cheap to enjoy the pricing for long.

I'm not exactly a regular, but can appreciate a drinking weekend. My last trip was during Hurricane Katrina, which has ruined Key West for me... after driving in on the sidewalk to avoid the deeper water in the road, we had a nice weekend with few tourists. Everything was open, but you could find a chair anywhere... not the usual experience.

Every other trip was too crowded for my taste, the sights are worth a visit, if only to say you were there... if you time the trip right, you could swing through Sebring for the 12 hour race. Traveling anywhere but Miami from Key West is a big deal... Florida has a lot of north-south miles.
 
I was thinking Miami but I haven't even looked. The idea came up a day or two ago. Maybe a week total for the trip.

Did someone say elbowtoasshole, count me in!
 
Last edited:
Laura thought that going to Key West in early March for her birthday sounded good, and like the kind soul I am, I offered to solicit help from the fine Floridians that are members here! @73 T&C @cantflip @67newport @65Fury440 @commando1 and any others I forgot.

So does anyone have any "must see" place to stop at, or restaurants we shouldn't pass up? I don't know anything about the Keys other than there's a lot of water everywhere, and Key West seems pretty liberal about anything.

Any tips or suggestions appreciated. Thanks FCBO!

My wife and I had a one day stop there on cruise we were on several years ago. Your wife may like The Key West Butterfly and Nature Conservatory. There is a trolley style bus that travels around with different stops that you can get on and off of at various places that is worth riding around on to check out the area. I would suggest spending some time just walking around the downtown area and the little shops and bars/restaurants. Be prepared for sticker shock on everything and always be ready to avert your eyes. Seeing topless senior citizens with body paint can result in traumatic visions that you will want to erase from your memory. There is a nature conservatory that is just okay if you want to see local animals. Enjoy!
 
Well, I'm sure it has changed a couple times over in the 2300 years since the wife and I were there for our honeymoon. There is a bar on the main Street(Duvall) and another one next to it, and another next to it,.and another, well you get the idea and we were a lot younger.
 
My first response to "things to see" was, the Georgia state line!:D
Key West is probably a "gotta visit once in your life" kinda place.
Miami, Key West and Orlando, in that order, are on my "places to avoid in Florida" list.
Touristy is one thing but, they seem to have been overrun by non-english speaking drivers from 3rd world countries. I swear I was the only customer in the Orlando car rental line not requiring a translator.
Having visited the Sunshine State all my life I've settled on Daytona Beach and Pensacola Beach as my go to beach front vacation spots.
I just avoid Spring Break, Bike Week etc.

And Jeff, thanks for the back roads tip to Orlando Airport. Perfect, not a soul in site at 4:30 in the morning.
 
Key West is indeed a "gotta visit it once" place. Three days is plenty IMO.

1) Breakfast at Blue Heaven. Eggs Benny with lobster is outstanding, and it's a cool outdoor place, roosters are everywhere but are not on the menu. http://www.blueheavenkw.com/breakfast
2) Dinner at Louie's Backyard. Pricey, worth it. Key West fine dinning with an ocean view | Louie's Backyard
3) The cemetery. All 100,000+ graves are above ground. Fascinating place. Friends of the Key West Cemetery
4) Order a cocktail at a bar, have a few sips, then (after paying) walk out with your drink to another bar. It's legal there, and really fun to do.
5) Rent a scooter so you can cover some ground and see the whole place in an hour, and an easy way to get to the cemetery.
 
We lived in Key Largo for a year, and KW was a regular monthly outing.
Things to see-
Mallory Square at dusk, Good street show.
Mel Fischer's Atocha museum.
Hemingway house. (Hemmingway cats are polydactyl, they have 6 toes, we ended up with one we adopted off the street).
Garden of Eden rooftop bar is clothing optional. Don't go if you're a prude.


If you like outdoorsy stuff, Pennakamp Reef in Key Largo has a glass bottom boat ride.
Also in Key Largo is Verne's underwater hotel. If you want to impress her, stay a night underwater.
Pilot House bar in Key Largo is a great place to have dinner. It has a glass bottom, lots of wildlife cruise through. Worth a couple bucks to start a good evening.
The weather is great 99% of the time.
We are about 8 hours north, if you get out this way, swing by!
 
I will admit to having a good time on Key Largo. It just seemed more my speed. Years ago the last available room throughout the keys was on Largo. One of the best vacations ever.
 
This trip is going to cut into the 66 Dodge fund, I guess it's a good thing you passed on the southwestern sheetmetal.:poke: Some things are more important than cars though. I know she is your girlfriend but I believe this still applies....Happy wife happy life:)
 
I figured you did because your talking about a trip instead of the best way to survive a Minnesota winter in your pickup truck
 
Back
Top