This isn’t a post about the obvious. This is a post about what we as Floridians must do in Key West. We all know about the bars on Duval Street.  Getting your picture taken by the buoy. That’s the tourist stuff and I know I’m guilty of it too. One time we went down for the powerboat races. We quickly got bored with it, ended up in a bar on Duval Street, got drunk and then on a bench in Truman Park. I had the most amazing discussion with one of the roosters that hangs out in that area. We talked about family, tourists, hurricanes, and stuff like that. It seems like most of my Key West stories are “we got drunk and….” I mean, why was at a rented house partying with a bunch of girls on a bachelorette party? Because I brought beer. That’s the Keys that you always hear about. And let’s not forget Fantasy Fest. Fantasy Fest is legendary.


This is a list of 10 must do things compiled by Key West resident Ian Wilson. Plus one bonus. So stop acting like you’re from Ohio and go see the real Key West. The one the locals know.

  • Fly to the Dry Tortugas

    There’s remote islands out there waiting to be explored and the best way to get the whole scene is not by boat. Fly in on a seaplane. There’s actually a seaplane that flies out of the Naples Airport, Salt Island Seaplanes. If you’re already in the Keys, Key West Sea Plane Adventures can fly you to Fort Jefferson. Seeing it from above is truly unique and landing a plane in water? Wow.

  • Grab A Kayak And Explore The Mangroves

    There’s a great kayak mangrove tour that heads out of Key West. Want a little more adventure? Kayak the Crocodile Lake National Wildlife Refuge in Key Largo. 

  • Grab a Sailboat

    If the wind picks up and it’s no bueno for diving or canoeing, sailing is always an option. The average cost for a Key West sailboat rental is about $950/day for 6 people. There’s a lot of other options.




  • Try your hand at paddleboarding

    This is the opposite of sailing. If the water is calm and clear, the view from a paddleboard can be amazing.

  • Snorkling

    All those things you can see while you’re paddleboarding – get in there with them.


  • See A Shipwreck

    There’s so many shipwrecks to explore they actually call it The Shipwreck Trail. Some are even 20 feet or less deep.

  • Fish

    You can fish in Southwest Florida, but fishing in the Keys is just – different.


  • Kiteboarding

    Definitely more adventurous than some of the other items on the list. More of a winter activity when the winds pick up. Anne’s Beach is a popular destination for this.

  • See Fort Jefferson in the Dry Tortugas - The Right Way

    When the ferry arrives and dumps off a couple hundred people things can feel a little crowded. The best time to explore is when the crowds aren’t there. You can camp, or better yet, sail there or fly in on a seaplane during off hours.

  • Camp in the Dry Tortugas

    As mentioned above, if you have the right equipment, you can camp near Fort Jefferson. Once the tourist leave and the sun goes down it’s just you, the sea, and the stars.


  • Drive to the Keys In No Hurry

    I did this once. Rented a convertible Mustang from Hertz and drove. We took 41 towards Miami, south on 997 through Homestead and then US 1 through the Keys. Best way to do this is on a weekday or you’ll get hung up in traffic but it’s a great way to see everything. We stopped in Homestead and got fresh mango milkshakes. Stopped at Robbie’s. Ate at little hole in the wall restaurants, and stayed at a BNB in Key West. It wasn’t cheap, but driving the overseas highway was definitely an experience.

    Here’s the view from Marathon.

    Never made it all the way to Key West.

    Posted by Joe Winner on Saturday, July 15, 2017



  • So I mentioned Seaplane

    It really is amazing. This is takeoff from Cabbage Key.

    Seaplane to Cabbage Key on a Sunday.

    Posted by Joe Winner on Sunday, December 10, 2017


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