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For our first post I came up with the idea to make a list of all the reasons you should visit. After all the purpose of this website is first to convince you to make a trip and second it’s to help you plan and make sure you don’t miss out on all the fun stuff to do. Feel free to message me with ideas that I have left off. I would love to make a post about 10 reasons to go back that give me a reason to get my ass back there.

Key West Is Fun

Is there a better reason to go. Maybe it will make you happy might be a better reason. And the fun is not just all the bars you can party like a rockstar. It’s like a treasure hunt because there are so many cool things to do that you never know what you will find.

Tons of Culture

When I say culture I mean stuff that isn’t common. There are tons of art galleries. There are things unique to the keys like the southern most point. There is music. The architecture is stunning. The food includes pretty much every variation known to man. What makes for culture. Music, art, food, and things to do? I’m not sure but it seems like an abundance of culture exists on the island.

It’s Relaxing

Seriously you feel like your on vacation. The island pace is slow and you don’t need to rush to do anything. We liked to sleep in and stay out late but you might also like to get up early and do some tourist things before it gets hot. In May I thought the weather was great. Not too hot to tire me out but hot enough to lay out on the beach. After a rain it was humid which was a little rough and early diners aren’t fun outside. I imagine anytime before June the weather is going to feel like your relaxing and on vacation.

Great Food

I admit I like to eat. The only thing I didn’t have there was Mexican. I did try Amigos but it did nothing for me. I had some incredible Italian at the New York Past Garden. The Stone Crab Claws are amazing. I know most of Florida has that but it’s sweater and I love eating crab claws the most. I had lobster rolls. Key Lime Pie. Croissants. Huge Homemade Cookies. Cajun. Cuban. All insanely good.

Sight Seeing

There are some great sites to see in Key West. It’s tough to pick a favorite. I’m going with the Key West Butterfly and Nature Conservatory as the most impressive. But here is a list not ranked in any particular order.

  1. Key West Butterfly and Nature Conservatory
  2. Ernest Hemingway House
  3. Harry S. Truman Little White House
  4. Key West Aquarium
  5. Mallory Square
  6. Duval Street (Like 6 St in Austin, Bourbon St or Gas Light District)
  7. Southernmost Point Buoy

Key Lime Pie

If your like me and you like Key Lime Pie it’s fun to try to find the best place. Pretty much every restaurant on the island serves it. Then there are a few places that basically exist to sell key lime pie. My favorite was Mattheessen but a wide margin. The place that comes up on the top of most best of lists is Kermit’s which I thought was terrible. It tasted like the stuff I can get at Trader Joes.


I’m going to do some research and post a little about the history of this. But there are tons of wild Roosters all over the Island. They are really pretty. And I found them entertaining. Not as noisy as you would expect. I think it’s because Key West was so isolated in the old days it wasn’t feasible to ship in fresh eggs and milk.

Live Music

The only thing I ever liked about Austin was the live music. Maybe they kept it too weird for me. The weird in Key West is right up my alley. My favorite place was called Duval Central which is next door to Sloppy Joes. This joint reminded me of the feel of Austin and 6th Street. The band was just particularly cool. You get a lot of Eagles and Tom Petty. Not much Jimmy Buffet. The one thing I was disappointed about was I didn’t get any live Reggae which is another one of my favorites and I expected to find it there. I might not have looked hard enough. Live music is all over. A lot of single guy bands basically doing Americana but it’s good almost universally.

Anything Goes

You can be yourself. There is a strong LGBT presence but you wouldn’t know. You can wear shorts and ugly Hawaiian shirts and you look cool. You can be cheap and look for specials or go as a big spender, it just doesn’t matter. You don’t see a ton of fake boobs and botox lip injections like you would in South Beach. It’s just a lot of middle aged people have a great time.

One Human World

This is the philosophy on the island. We are all humans of the same world. Kind of interesting concept that a small island thinks that way. But there is no crime. Everyone is nice to each other. Everyone is happy to help or if you have a question literally you can ask anyone and they will not act like your bothering them. It’s like one big happy family. It’s really nice. Peace and love kind of thing every where you go. It’s really relaxing.