Destination Guide: Key West

The end of Highway 1 in Key West. This road is 545 miles in length and stops at this intersection.

The end of Highway 1 in Key West. This road is 545 miles in length and stops at this intersection.

Have you ever been to the end of the road?

That is literally an opportunity when you go to Key West. I have always been fond of the drive from mainland Florida down to Key West. As you leave Miami proper you embark on a road headed to a world of “island life.”

The Florida Keys are a splendid place to live or take an expedition to. From diving to pristine beaches to excellent seafood it gives you a chance to live the island experience without having to even leave the lower 48 of the United States.

Key West is the last stop on the road in the keys and is the rowdiest, strangest, and my favorite part of the Florida Keys to explore. It’s a stop at the bottom of the United States and one you won’t soon forget!

I’ll share some of my faves to ensure you have a fun long weekend in Key West that goes beyond just sitting inside of Margaritaville. (Though some take pleasure in doing just that!)


Things To Do:

  • Watch the Sunset Celebration at Mallory Square. Drinks, random entertainment (like the “Cat Man”), and a round of applause for another day on the island happens every single night.

  • Tour the Hemingway Home. Ernest Hemingway wrote about 75% of his published works at this home and you can tour it, with or without a guide, and say hi to the 56 residents. (All cats descending from one that lived there with Hemingway in the 1930’s.)

The Hemingway Home from out front.

The Hemingway Home from out front.

  • Take a stop down to the Southernmost point of the Continental United States and get a photo!

  • Kayak, SUP, or do yoga at Lazy Dog! We did the eco adventure tour and it was a highlight of my trip and one of the coolest kayaking trips I have ever taken!

  • Climb aboard the Yankee Freedom III for a day trip to Dry Tortugas National Park.

Panoramic view of Fort Jefferson on the Dry Tortugas.

Panoramic view of Fort Jefferson on the Dry Tortugas.

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Places to Drink:

  • The Green Parrot. This bar has been around for a loooooong time. It’s a “Sunny Place for Shady People” and features great live music and free popcorn!

  • Captain Tony’s Saloon. Nothing fancy about this place except you can get a plastic mug cup to take home. My parents got them when I was a kid and I drank out of this cup for about two decades so it’s got some nostalgia!

  • Sloppy Joe’s. The original hangout bar of Hemingway’s when he lived there. Rumor has it he once dragged a urinal from this bar and left it in his front yard. He was a rowdy dude to say the least.

  • Anywhere with a view of the beach and your feet in the sand. Honestly wherever you are staying is your best spot. Waves crashing, toes in the sand, and the view of the water. That beats sticky floors and four dollar beers for a few of your nights!


Places to Eat:

  • Garbo’s Grill. Excellent tacos and fun story behind it!

  • Blue Heaven. My parents, and hundreds of others, number one spot to get yo Island Brunch on!

  • Santiago’s Bodega. Haven’t eaten here but was recommended to me several times and the wait was an hour plus whenever we checked. Worth a shot to me!

  • Hurricane Hole. More amazing tacos, right on the water, and a perfect pre adventure tour spot with Lazy Dog. (Located right next door.)

  • Whatever you catch during the day fishing and prepare at your house or at a restaurant that will take care of it for ya!


Key West is a fun and quirky destination to visit. It can be a bit loud if you just stay on Duval Street but the same could be said if you never leave Bourbon Street in New Orleans or campus in my residence of Columbus Ohio.

My Key West is one rich with history and adventure. It’s a place that I can feel the beautiful land of Cuba holding its influence as well as the wild writings of Hemingway.
It’s a place that can be as wild or quiet as you choose to make it.

This should give you a start in some of the exploration of Key West!
Have you been and have something to add? Put in your comments below!

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Because Adventure Travel Feeds the Soul,
Mike R and the Hashtag 59 Team

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