We first flew into Miami from Hawaii (first stop Atlanta – connecting flight to Miami). After picking up our rental car, we drove for approximately 3 and a half hours down to Key West.



  • Be sure to check your rental that there are no warning signs on the dash. In the same time, have your partner (if you are traveling with others) check the outside of the car and either capture video or photo of existing damage on the vehicle this may save you insurance troubles and any extra rental expenses if need be.
  • Keep an eye on your gas and if there is one available on the way to your destination. More about road trip tips in particular can be found here.
  • In Key West, Mallory Square is the center of attraction. Bars, food, night life and more activities can be found here. Head there first to check out all the action!
  • Duval Street is the more laid back area of Key West and is the main street where the town developed around. It’s the Old Town of Key West area.
  • Depending on where you stay, there is transportation available, provided by your hotel. If possible, opt to take the shuttle or other means of getting to the central part of town because parking ranges from a minimum of $20 – $30. Street parking is scarce as well.
  • No shuttle service? No problem. Look for a rental shop that offers mopeds, golf carts or bicycles! You can find a good deal a little outside of Key West’s center, where many hotels are located. These rental places are accessible all over, so it shouldn’t be too hard to find.


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We enjoyed our stay at The Gates Hotel – A newly opened and invigorating hotel that provides shuttle service to Mallory Square and rentable bicycles. There are other hotels throughout the area and closer too. The Gates is only a 10-minute drive away from the central area of Key West.


DSC02241In Mallory Square, there are many things to do, all within walking distance. It can be explored in one day or spread over a few days. Walking around is the best and most convenient way to navigate through the area.

DSC02232Key West Aquarium

DSC02228Shipwreck Museum


DSC02230Apart from attractions, three are also small markets, a mini-mall, and of course, eateries of all taste cravings!



Harry Truman’s Little White House!

DSC02249 copyOur first day was rained out for the first half which was a perfect time to visit the indoor museums. It cleared up during the afternoon which we took the opportunity to bike around! If you get the chance, we highly recommend renting a bicycle or even moped and explore the little alleyways, open for exploration.


DSC02277 copyThe most fun we had during our visit in Key West was thanks to Fury Adventures. It was a full day of excitement in, under and over the water. Parasailing, Jet-skiing, mid-ocean water park and snorkeling on the third the largest reef in the world, in the Gulf of Mexico.

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467A6347 copyAfter our 5-hour excursion with Fury Adventures, we headed back to The Gates for a quick change, took the free shuttle to Mallory Square and signed-in for a sail with Danger Charters for a wine & sail “around the world” (through taste).

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467A6501 copyWe followed up a night of wine tasting and delirious fun with a food tour via Key West Food Tours.



Of course, when in Key West, you have to check out the most touristy spots – these spots came in the form of landmarks. Mile 0 and The Southern Most Point (in the Continental USA), to be specific, are must-see sites.




There was a food truck (The Blind Pig) at The Gates Hotel which was where we ate breakfast, lunch, and dinner. It was advantageous to get our meal to-go and relax in our room!





We ate at the famous Sloppy Joes Bar just outside of the Mallory Square shuttle drop off. It was very convenient and provided a lively ambiance for all ages.

467A5985The Sloppy Joe!


DSC02227Last but not least, the world-renown Key Lime Pie. Almost every place selling it states they were the “original” Key Lime Pie Bakery which is good for business! This delicacy could be found easily in and out of the busy streets. We had ours at Blue Heaven Bar & Restaurant – according to Mary, the name truly does live up to the taste.

There you have it! How we spent a full three days in Key West! There is so much to do in the little town, but I feel like we were able to cover all the main things any tourist would like to visit. If you have any recommendations, please leave us a comment! We hope this itinerary gives you ideas on how to make the best of your Key West trip! Thanks for visiting.



  1. I love that everyone is claiming to be the “original” key lime pie! Sounds like a tasting tour is called for!

    • Hahaha! I know, right?! Everywhere throughout Key West are sign “original/home of the Key Lime Pie”. Even on brand new establishments say it. Hard to tell where it really came from. I’m betting it was invented in someones home haha. Thanks for the comment!

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