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Our Key West Bucket List Must-Do’s

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Brimming with sunsets, happy hours, cats and key lime pies, Key West was the perfect place to kickoff our 9 month cross country road trip! With 5 days to spend on this “salty piece of land,” we made sure to live every moment in a way that would make even Jimmy Buffet proud.

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1.) First up on our list, we have the Southernmost Point. You’ll know when you’re close because you’ll see the Southernmost EVERYTHING within a mile’s radius from this spot. It’s free, 90 miles from Cuba, picturesque and needless to say, it’s extremely popular. Go first thing in the morning to avoid waiting in line. We rode our bikes with our tripod in hand and made the stop around 7:15am before breakfast. With thankfully no line yet, it was the perfect spot for a Southernmost handstand and a romantic Southernmost kiss:

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2.) Another beautiful spot that’s absolutely free is the historic West Martello Tower. Drew and I had a great time roaming and taking photos with the beautiful flowers and incredible trees here, making it way worth our time.

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Note: You can also take the Old Town Trolley to just about every single one of these famous places, more on that below.

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3.) We don’t generally lean toward doing tours and such, but we’ve come to appreciate how much one can learn about a place when you take the time to sit and listen. The Old Town Trolley Tours are not only a great way to learn about the rich history of Key West, something we knew nothing about, but it’s also a great way to get around town! One ticket gets you access to ride the hop on hop off tour for 2 days. Whether you’re museum hopping, pub crawling or just looking for a chill way to spend an afternoon, it’s a fun and easy way to get around.

While on this tour, we learned about where to find the best dark chocolate dipped key lime pie (see bucket list item #7) and we got to see one of the most famous, and most stolen signs in America! Mile Marker 0 marks the end and the beginning of US-1’s 2,377 mile route up the East Coast! Another reason why Key West was the perfect place to start our big adventure.

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4.) Another spot worth a visit, especially if you’re traveling with kids or trying to take cover from a rainy day like us, is The Key West Aquarium. Located right next to Mallory Square it’s a great place to stop in before or after catching the Crazy Cat Man show (see Bucket List item #6). If anything, you gotta at least stop by and take a picture in the ginormous Shark jaw!

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You’ll see some beautiful fishies, like this impressive Lionfish:

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And you might even find a new friend! This guy literally didn’t move for about 5 minutes:

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5.) Did you know that back in the 1850’s Key West was considered the richest city per capita, in the US? Due to the prevalence of shipwrecks on Florida’s treacherous reefs caused by stormy weather, or a captain’s inexperience with the area, ships with valuable cargoes were continuously foundering just off shore. As a result, wrecking and salvaging soon became the island’s primary business and people came from all over to bid on the valuable salvaged items. The people of Key West became extremely wealthy on the proceeds and being a scuba diver was the best paid job in the land! How do we know all of this? The Mel Fisher Maritime Museum and the Key West Shipwreck Treasure Museum are overflowing with historic jewels and gems, the literal and figurative kinds!

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6.) As you may already know, Key West is home to many, many cats, including Hemingway’s famous 6-toed cats and the Crazy Cat Man’s crew of “flying house cats!” Every evening at sunset, Dominique, aka. Cat Man, sets up his kitty circus and puts on an unforgettable, famous show that no trip to Key West is complete without!

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He can be heard yelling his famous lines, “Go back to your seat. Say where you are!! Do what you want… Hurry up, take your time!!”

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7.) Now that we’ve covered some of the must-see museums, tours, and shows, we can finally talk about that mouth watering, perfectly sweet, perfectly tart, PERFECTLY PERFECT, slice of dark chocolate dipped key lime pie… and my mouth is now watering uncontrollably. As you walk down Duval Street, you’ll see restaurants, shops and stands all claiming to have “The best key lime pie in Key West,” but thanks to our awesome Old Town Trolley tour guide, we know where to find it.

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Kermit’s Key West Key Lime Shoppe, which is brimming with free samples of key lime everything! is home of this masterpiece. Sit, watch and drool over this short video of our divine experience (excuse the blurriness, we’re still working on our videography skills):

8.) Need something to help wash down that key lime pie? Luckily there are plenty of options in this land of endless 5 o’clock somewhere specials. Our fave bucket list option for this one is the fun and delicious pineapple drink, complete with swinging monkey, flamingoes, palm trees and to top it all of… a cherry of course! These can be found in Mallory Square just about everyday at sunset.

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9.) One thing that Key West isn’t famous for is its beaches, all of which are manmade, but one of our personal favorite spots ended up being Smather’s Beach, a long, serene stretch of sand, perfect for picnics, paddle boarding and running or biking along the boardwalk. We found something fun to do here just about everyday:

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10.) With a ton of ways to enjoy this tiny slice of paradise, soaking in a classic and unforgettable Key West sunset tops off our list.

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In the famous words of Jimmy Buffet, “The lower the latitude, the better the attitude.” You can’t go wrong with a trip to Key West.

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22 Comments

  1. Reply

    Kati

    July 9, 2017

    Where was that tree? It’s beautiful & would be perfect for my trip next week & my plan to eat, drink & photograph my way through key west

  2. Reply

    Lois

    June 6, 2017

    Just planned our trip for October, and these tips are helpful….thanks for your input..

    • Reply

      Brittany Rouille

      June 6, 2017

      Hi Lois! October is the perfect time to be there, the weather will be beautiful and the crowds will be scarce 🙂 So glad to help!

  3. Reply

    Chanel | Cultural Xplorer

    May 7, 2017

    Thanks for the tips! Looking forward to visiting Key West in a few months!

    • Reply

      mrandmrsadventure

      May 7, 2017

      We’re glad you found us 🙂 Have an awesome time!!

  4. Reply

    AuntniniKW

    March 12, 2017

    Key West is a good place to visit. The experience is different than living there. Smather’s Beach is nice, from the sand. Do not go into the water there. You will come out feeling slimy…there is a reason for this….it’s called a sewage outlet. If you want a great beach experience, and you want to stay within the 2×4 island that is Key West, then go to Fort Zachary (you will need swim shoes as there are a lot of rocks and coral, but there is a fort within the park to explore with great views, and maybe see a pirate ship reenactment). You could take a ferry or small plane to Fort Jefferson (off the coast of Key West). The other option, which I prefer, is Bahia Honda in Big Pine Key. It is a State Park and has simply gorgeous beaches. There’s a neat place to eat on No Name Key, which is nearby if you can find it. It’s called No Name Bar…really good pizza and you will most likely get a chance to see the itty bitty key deer (my husband got licked by one..). They are not afraid of people, but it is not legal to feed them, no matter how badly they mooch. The Blue Hole is nearby and really quite an interesting story behind it. Also, if you are into this kind of thing, the cemetery in Key West is interesting. I lived about a block from there on Olivia in Old Towne. Lots of homeless…lots of interesting stories regarding them….again, visiting is a different experience. Just like anywhere, there are opportunistic thieves…Don’t leave your things unguarded or doors unlocked. Don’t learn the lesson the hard way.

    • Reply

      Brittany Rouille

      August 21, 2017

      So sorry for the delay in getting back to you, we thought we had replied to your wonderfully informative comment! My family lives in Florida so we will be sure to explore the places you mention when we return. The cemetery and those stories sound absolutely fascinating + the key deer sound adorable! + The Blue Hole + No Name + Bahia Honda! We really appreciate you taking the time to add to our list! Sending you hugs from us and our camper van in Norway!

  5. Reply

    jeanette hamm

    February 26, 2017

    Thank you for this! My wife and I got married last May and plan on having our honeymoon in key west and I was wondering what would be some good and not so expensive places to stay at?

    • Reply

      mrandmrsadventure

      February 27, 2017

      Congratulations you 2!! You are going to love The Keys! Being that we stayed in our camper van we don’t know of any places to stay in particular, but we can recommend looking on AirBnB.com, that’s where we always go to find the best places and prices 🙂 Have a wonderful time!

  6. Reply

    Michele

    February 24, 2017

    Glad I found this. Heading to KW soon. Flying into Miami to drive down to KW. I drive a lot for my job so the drive from Miami to KW will not be bad at all. A friend and I are taking our daughters down for their HS Senior spring break. This cysitc fibrosis patient is making it bucket list trip including snorkeling (even with 50% lung capacity). I’m ready to spend a week there with a little sight seeing and a little relaxing.

    • Reply

      mrandmrsadventure

      February 25, 2017

      Sounds like you’ll be with an adventurous bunch, and snorkeling is the perfect addition! The weather has been so nice down there, you are going to have a fantastic time! Glad you found us and thank you for taking the time to write 🙂

  7. Reply

    april

    January 22, 2017

    I’ve read several Key West blog posts, and this one is the most helpful. We are supposed to fly to Miami this week, and my husband just suggested we drive down to Key West instead. We are looking into which would be a better fit for us. the one draw back will be the 7 hour round trip we will spend in a car, losing some of our fun time. If we go to Key West we’d have 3 days there. We will be leaving the snow and freezing cold for some warm weather and sunshine.

    • Reply

      mrandmrsadventure

      January 23, 2017

      Hi April! Aw, we love hearing that you found our post so helpful! Key West is worth the drive. I know Miami is more convenient, but honestly Miami isn’t our favorite city… it doesn’t even make our list of top 10 – but that’s us, some people love it! Key West will offer you more of a retreat feel, you will find peace, art, beautiful water, great music, fun restaurants/bars and time just runs at a better pace down there 🙂 If you can, be sure to stop at Morada Bay Cafe for a bite or drink in Islamorada – it’s our favorite spot in the keys + it’s 5 minutes from the house we got married at 🙂 THIS is what it looks like: https://mrandmrsadventure.com/2016/05/25/our-starry-skied-seaside-wedding-in-islamorada-florida/ HAVE A WONDERFUL TIME!!

  8. Reply

    Shannon Miller

    August 18, 2016

    I live in Southeast Florida and I can NEVER get enough of the Keys and KW. Although part of Florida, it has a completely separate atmosphere about it.

    • Reply

      mrandmrsadventure

      August 21, 2016

      I was born and raised in Ft Laud and while I love it because my family is there, it’s not exactly my cup of tea. But THE KEYS! Now I could drink a cup of that everyday? Drew and I actually got married in Islamorada!

  9. Reply

    johanna jani

    April 21, 2016

    Thank you for these amazing tips:)

    • Reply

      mrandmrsadventure

      April 22, 2016

      Hope you have a great time!

  10. Reply

    Christina

    July 7, 2015

    Awesome tips! My bf and I are heading down to KW for a weekend soon! We will definitely hit most of the spots you mentioned. Thank you for the helpful blog!

    • Reply

      mrandmrsadventure

      July 7, 2015

      Have a blast! We’re glad you wrote to us 🙂 Adventure always D & B

  11. Reply

    Lue Clark

    February 12, 2015

    Perfect. We still hope to make this a October get away.

    • Reply

      mrandmrsadventure

      February 12, 2015

      Give us a call before you go, we’d be happy to help 🙂

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