Our Key West Bucket List Must-Do's

key west sunset, things to do in key west, key west bucket list, things to do in key west, adventure couple

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.

key west things to do, southernmost point, southernmost kiss, southernmost point kiss, adventures in key west, mr and mrs adventure, southernmost yoga, handstand 365, best handstand, famous handstand,

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:

key west things to do, southernmost point, southernmost kiss, southernmost point kiss, adventures in key west, mr and mrs adventure

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.

west martello tower, free things to do in key west, places to go in key west, key west bucket list

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

trolley tour key west, old town trolley key west, historic america tours, best tours in key west, things to do in key west, key west bucket list, head in hole pictures

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.

end of us-1, end of the road, mile marker 0, famous key west sign, famous mile marker 0 sign, must see places key west, key west bucket list

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!

key west aquarium, things to do in key west, key west attractions, key west bucket list, giant shark teeth, megalodon short teeth couple, JAWS, adventure couple with shark

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

key west aquarium, things to do in key west, key west attractions, key west bucket list, lion fish, striped brown and white fish, beautiful fish, key west fish

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

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!

treasure museum key west, things to do in key west, family activities key west, key west tours, key west historical tours, ship wreck history key west

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!

crazy key west cat man, key west cat man, flying house cats, things to do in key west, key west bucket list, weirdest shows in the world, dominique the cat man, sunset shows key west, key west cats, key west cat show

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!!”

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.

best key lime pie in key west, best chocolate dipped key lime pie in key west, key west bucket list, best of key west, old town trolley tour

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.

key west bucket list, must do in key west, five o'clock somewhere, head in hole, best of key west, fancy drink, pineapple drink, umbrella drink

key west bucket list, must do in key west, five o'clock somewhere, head in hole, best of key west

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: