To craft rugged luxury itineraries for open minded explorers seeking faraway and bespoke experiences
Full disclosure, I might be a little biased in how much I love Key West, probably because I was born there! I’m a true native Conch, born into the Conch Republic, so I’ve spent my fair share of time on this little 2×6 mile wide Island. Every time I come to Key West I find something new and exciting to do. As a 7th generation Floridian who has lived in Florida for 25 years, I feel pretty qualified to share with you what I have found to be the best things to do in Key West!
I know it sounds cheesy and corny and the tourist thing to do, but that’s because it is! I know taking a trolley ride doesn’t sound like the most exciting thing do to in Key West, but it is one that will help you get the lay of the land and learn a little bit about the history of the Conch Republic. Key West has Old Town Trolley Tours (the same company that runs the ones in St. Augustine) and they are fabulous! Take a quick 3-hour tour and learn about Key West with a cool breeze, and you may learn about things to do in Key West that aren’t on this list!
Something that will likely happen without you even trying while you are in Key West is taking a stroll down Duval Street! This is a great street to grab a to-go beverage, look on, and people watch. Pop into different shops, there are so many with lots of different items for sale. From hammocks to shoes, Duval Street is selling it all.
For my LGBTQ+ readers, Key West is 100000% a destination for you! You can miss the gay section of Duval Street, it’s marked with beautiful rainbow crosswalks! Key West has always been known for its inclusivity to anyone and everyone.
An absolute must while you are in Key West. Stop in for some fantastic Sloppy Joes and a drink and listen to live music in one of the most historic bars in Key West. Sloppy Joes has been located on the corner of Greene Street and Duval Street since 1937. One of it’s most famous patrons over the past was none other than Key West resident, Ernest Hemingway. Each year the bar hosts an Ernest Hemingway look-alike contest!
The Florida Keys are known for their amazingly clear blue water, thanks to the proximity of the Gulf Stream that runs right up to them! Charter a snorkeling trip to one of the many reefs and see incredible wildlife! Some of the animals you may see include coral, anemones, sea urchins, turtles, dolphins, reef fish, sharks barracuda and SO much more!
Located just around the corner from Sloppy Joes lies another famous bar to Key West (are you starting to see a pattern here? There’s a LOT of drinking going on in Key West). Captain Tony’s Saloon has had many famous guests in its bar stools as well including Jimmy Buffet, JFK, Ernest Hemingway, Shel Silverstein, and John Prine.
Above the entrance to the saloon lies a giant Jewfish (aka a Goliath Grouper) that Captain Tony caught and preserved. It is said that if you stand backwards to the door and toss a quarter into the out of the grouper that good luck will follow you until you leave the island. Try it out for yourself!
Don’t miss out on all the specialty drinks that Key West has to offer. This craft cocktail pub crawl is one of the best things to do in Key West!
A little off the beaten path, but if you want the best Cuban cafe con leche in your life, it’s worth making the trip over to Sandy’s. This little laundry-cafe combo has been in business for longer than I can remember and is a perfect little Key West hang. Order a cafe con leche – otherwise known as liquid cocaine, and a Cuban sandwich, and continue on your stroll through the historic district.
If you’ve got ample time in Key West and are looking for a fun day trip then look no further than Dry Tortugas National Park. Located 70 miles west of Key West, the only way to get out to this National Park, which hosts Fort Jefferson, is by boat or seaplane. The Yankee Freedom is a ferry boat that runs daily to the Dry Tortugas, or you can hire a private boat, though the cost will be more.
Why visit the dry Tortugas? Beautiful waters, great snorkeling, a historic fort, and untouched land makes the Dry Tortugas an immaculate destination and a wonderful addition to any trip to the Florida Keys.
There are tons of boat tours to take while you are in Key West, but I wholeheartedly recommend taking a sunset cruise!
If you are visiting during the summer see if the Jolly Rover II (a sister ship to my family business, the Schooner Freedom) is sailing. If they are out on a boy scout charter see if the Danger Schooner Fleet, the Schooner Appledore, or the Fury Catamaran Cruises with live island music are sailing. Another great option is the Sebago charters. Or you could also try out the America 2.0 – one of the vessels sailed in America’s Cup races!
If you are looking for the sister ship to the Schooner Freedom (my family’s business) then look no further than the Jolly Rover II.
If you are visiting during the winter, most of those boats will still be there, but there will be even more options. My recommendation for the winter is to sail onboard the Schooner When and If – a 1938 schooner built for General Patton. I sailed onboard Schooner When and If during my travels to Salem, MA and it was absolutely FABULOUS! Be sure to check them out if you’re in Key West November through March!
One of America’s greatest authors spent some time in Key West, and we’ve already mentioned him a few times. Ernest Hemingway lived in Key West from 1931 to 1939, though he kept the title to the house until his untimely death. This beautiful home is available to tour and learn about its history and the history of Hemingway while he lived in Key West.
Along with a tour of the home, you will meet descendants of Hemingway’s famous 6-toed cats, as there are over 100 on the property. You are welcome to pet and play with the cats and kittens, but please, do not pick them up!
Admission is $15
Key West isn’t just drinking and good seafood. There is a darker and haunted history to this little island that you should take the time to learn about. If you guys have been following my blog for awhile now, you know that ghost tours are among some of my absolute favorite things to
No trip to Key West, or Florida even, would be complete without some delicious Key Lime Pie! Now, I’m not really a sweets person myself, but there’s not much I wouldn’t do to get my hands on some homemade Key Lime Pie. You can get Key Lime Pie in almost any restaurant in Key West, but be sure to ask if it is made in-house! If it’s not, save your pie-eating for elsewhere.
You can also visit the Original Key Lime Pie Bakery, located on, appropriately, Greene Street. (PS – if you’re key lime pie is green, instead of yellow -that ain’t right!)
Nothing beats fresh seafood caught directly from the ocean, except maybe someone else doing the catching and the cooking! There are so many restaurants in Key West, but you want to make sure you get the freshest food and you also want to make sure you have a good experience, so find somewhere with live music!
A great place a little bit off the beaten path is Smokin’ Tuna. We took my dad here for Father’s Day this year and we loved it. Great food, great music, great drinks, and we had some delicious Key Lime Pie for dessert as well!
This might be a no-go for some (including me) but if you’re wanting a totally unique experience, you’ve got to visit the Garden of Eden. Located on Ducal above The Bull and The Whistle – this bar is clothing -optional (this whole city seems to be this way on occasion).
For a week of parades, parties, and the Mardi Gras of the gays, visit during Fantasy Fest, held on the two October weekends closest to Halloween. This giant party is again, clothing-optional, and while not an official LGBTQ+ event, the community has accepted it wholeheartedly. This is a festival for anyone who loves to feel free and get a little wild and weird! I have not been myself personally, but it is on my bucket list of festivals to attend!
Wild costumes, body painting, large parties, and balls adorn this 10-day event. If you’re feeling a little tentative, head down during weekdays when things are a little calmer, and the hotels won’t require a 3-night stay.
Looking to get a fresh catch yourself? Head on a half-day excursion with a deep-sea fishing boat to try your hand at casting the rod. You’ll never know what you might catch!
Looking for water sports while you are visiting the Florida Keys? Barefoot Billies at Casa Marina Resort does great work. They are located right next to the Southernmost Point and will get you set up on some fun activities! Oh, and fun fact, my parents ran this watersports business 91-99 when it was Key West Watersports!
Florida has some of the best sunsets in the world – there, I’ve said it! While yes, I may be a little biased on that, I have seen a LOT of Florida sunsets, so you can rest assured I am a good judge. Head to Mallory Square during your travels to get an amazing Key West sunset that you will be sure to remember.
Get there early, as it tends to get crowded pretty quickly and you want to have good seats. Bonus points if you bring a bottle of wine and some snacks. Make sure you stay after the sun has gone down as well, as that’s usually when the best colors are to be found!
This small island town has another unique boast among many. Key West is the Southernmost Point in the continental United States! Take your photo at the Southernmost Point, and while you’re walking there, be sure to make a pit stop at Mile Marker Zero, the starting point of Highway US1, which runs from there all the way to Maine!
The Shipwreck Museum tells a different tale of Florida’s Southern Isles. There are loads of shipwrecks off the coast that you can snorkel, and this museum tells you all about them and the history associated with them. Definitely an interesting spot to hop out of the hot Florida sun for a few minutes and learn some history.
While not known for its sandy beaches, if you’re looking to soak up some sun, you can always head to Smathers Beach. It’s one of the cities larger of the 4 beaches and is well known as a spring break spot. There are bathrooms, showers, and volleyball courts. Parking is $4 an hour.
Last but not least one of the best things to do in Key West is to visit the Lighthouse. This lighthouse was opened in 1848 with a woman as it’s keeper, nearly unheard of for its time. Take the tour of the tower and the Keeper’s Quarters and learn all about life as it would have been. To visit the museum and climb the 88 steps, admission is only $12 and well worth it.
When I originally wrote this article, I only wanted 21 Items, but then I remembered KINO Sandals! So here is your bonus item of things to do in Key West! This little shoe shop in Key West hand makes all of their shoes, and they are comfortable and a Key West staple!
KINO Sandals represents the true American dream. A couple came to America from Cuba with a plan in mind and $3000 to start their sandal shop. The current location of KINO Sandals has been there since 1976, and they were in business for 10 years before that. They have several different styles to choose from, so be sure to pop by and get a pair, for the quality of leather and the story you are getting these shoes are incredibly priced. Most only cost right around $20. Or if you forgot to buy a pair, visit their online shop!
*This post contains affiliate links at no cost to you. Why affiliate links? They help keep this blog running and a free resource for you to use! Thank you for your continued support.*