We’re going back to Key West!
After our visit in 2025, Exploring The Sites in Key West For The First Time, we didn’t expect it would be long before this quirky little island found its way back onto our travel plans. Our first trip was all about discovering Key West for the first time. We explored the famous sights, wandered the streets, sampled the food, and tried to figure out what makes this tiny island so special.
There are some places you visit once and check off the list. Then there are places that pull you back. Key West is definitely in the second category. Welcome to Key West Take Two: New Discoveries, Old Favorites and Island Surprises.
This visit comes with a different perspective. We don’t need to race around trying to see everything for the first time. Instead, we can slow down, revisit a few familiar places, and pay attention to the things we missed before.
And that’s the fun of returning to a place you’ve already visited. You see it differently. Come along with us as the Cajun Explorers return to Key West. We may have been here before, but we’re betting this little island still has a few surprises waiting for us.
Arriving in Key West
We flew above the beautiful blue ocean coastline on a sunny afternoon. As we approached the airport, we saw the Civil War era Fort Zachary Taylor (1845-1866). Upon arrival, we enjoyed the new airport concourse A which is now open since our last visit to Key West. This 48,000+ square foot concourse features air conditioned glass jet bridges and no tarmac arrivals. A huge improvement since our last trip.
A week of fun with friends as we celebrate my birthday
This time, our Key West adventure wasn’t about checking off the usual tourist attractions. It’s about celebrating my birthday with friends and discovering more of the island’s personality. We can wander streets we hadn’t explored before, find new places to eat and shop, and enjoy the wonderfully quirky character that makes Key West unlike anywhere else.
Of course, some things were worth seeing again. After all, you can’t return to Key West without enjoying a little of what made you fall for the island in the first place. But rather than simply repeating our first trip, we wanted this visit to tell a different story. What happens when you look at a familiar destination with fresh eyes.
But first, let’s kick off the trip with coconut mojitos, lunch and dinner with our friends Robyn & Rob. Cheers!
We Came for the Sunset… But Key West Had Other Plans
Every destination has a personality. New York is loud. Paris is romantic. Las Vegas never sleeps. Then there’s Key West. Key West wakes up whenever it feels like it, wears flip-flops to just about every occasion, and seems perfectly content if your only accomplishment for the day is finding the next cocktail or slice of Key lime pie.
I always knew Key West is mostly beaches, boats, and bars. I’m not wrong. But I also wasn’t prepared for the wildlife, especially the chickens, lizards, and iguanas that are everywhere. But seriously…the chickens run this island.
They wander across sidewalks like they own the place, crow outside your hotel window without any regard for alarm clocks, and somehow always appear in your vacation photos. By the end of the week, I’m now convinced they are judging us tourists. Honestly, they probably are.
As the sun begins its slow descent. For just a few minutes, everyone stops talking. Even the chickens seem quieter. The sky turns shades of orange, pink, and purple that no phone camera ever captures quite right. When the last sliver of sunlight disappears below the horizon, complete strangers applaud. It’s one of the few places where clapping for the sun somehow makes perfect sense. One of the top things to do in Key West is attending the nightly Sunset Celebration at Mallory Square.
Strolling down Duval Street
No trip to Key West is complete without strolling down Duval Street. This renowned street stretches from the Gulf of Mexico to the Atlantic Ocean and features local shops, restaurants, live music venues, art galleries, and numerous spots to quench your thirst with a refreshing drink. Every block has something different, making it one of the most popular attractions in Key West. Whether you’re shopping for souvenirs or simply people-watching, Duval Street captures the fun spirit of the island.
Since we’re here during the “off season”, we experienced a very laid back, calm atmosphere without the packed tourist crowds.. Perfect for us.
Island Priorities
Time works differently here. Some places encourage you to move faster. Key West encourages you to slow down. It might be the only place we’ve visited where doing absolutely nothing feels like a productive day. Suddenly your biggest decision is whether to walk another block for homemade ice cream. Or, whether it’s too early for another frozen drink.
Spoiler alert: In Key West, the answer is almost always “No.” Somehow we’re perfectly okay with that.
The Unexpected Souvenir
We came home with the usual keepsakes. A magnet, a t-shirt and way too many photos. And then there was the no-see-um situation. Apparently, Key West has a souvenir program we didn’t know about. No tickets required, no checkout lines, and no gift receipts. Just stand outside for a while and let the locals have a little snack.
We never actually saw the no-see-ums, but they certainly saw us. In fact, I’m beginning to think they had our itinerary. They waited until we were relaxing, enjoying the tropical breeze, and then they launched a coordinated attack… By the second day, several of us looked like we’d lost a fight with a very tiny, very angry army.
The itching was impressive. The number of bites was even more impressive. And explaining to people that were attacked by something we couldn’t actually see made us sound like we’d spent our vacation fighting imaginary insects.
“Where did you get all those bites?”
“Key West.”
“From what?”
“Something called a no-see-um.”
“So you didn’t see it?”
“No.”
“But you know it was there?”
“Trust me.”
Let’s just say our souvenirs came with a delayed delivery.
Travel Tip: Don’t forget to pack sunscreen, insect repellent and lots of cortisone cream. You’ll thank me later.
However, our best souvenir isn’t something we packed in our suitcase; it reminds us that we don’t have to rush every trip. The best memories come from spending time with friends, conversations with strangers, wandering streets without a map, or laughing at another fearless rooster strutting through town like he owns the place…maybe he does.
Quirky and unusual Key West experiences we missed the first time…
Captain Tony’s: where the dead have a seat at the bar
We then visited Captain Tony’s Saloon, where Key West apparently decided that a normal bar was far too boring. Walk inside and you’ll find a tree growing right through the building, bras and dollar bills hanging from practically every available surface, and—because apparently a tree and a collection of underwear weren’t enough—a tombstone. Yes, a real tombstone. Legend has it that they buried Captain Tony’s former wife beneath it, because the building stands on what had been a cemetery. Most bars have a jukebox. Captain Tony’s has a tree, a tombstone and enough stories to make you wonder whether you’re having a drink or accidentally checking into the afterlife. Only in Key West can you order a cocktail and find yourself standing next to someone’s grave. We figured we’d better finish our drink quickly—just in case the tombstone had a reservation for us.
And here’s the part that made us look down at the floor a little more carefully: during renovations in the 1980s, workers reportedly found the remains of 15 to 18 people beneath the floorboards. The building earlier served as an icehouse and also functioned as a morgue, so people generally associate the remains with its earlier history. So while you’re standing there enjoying your drink, just remember—you may not be standing on solid ground. You may be standing on someone’s final resting place.
Two tombstones stand inside the bar: one for Elvira Edmunds, whose marker workers reportedly discovered during the renovation, and one for Reba Sawyer. The Reba story is much less certain—some accounts say her husband brought her headstone from the cemetery after discovering her alleged affair, while other accounts suggest some of Captain Tony’s stories became embellished over the years.
The Hanging Tree
And then there’s the tree. Not just any tree, mind you—the infamous Hanging Tree. According to Key West legend, this tree was once used to hang pirates and other unfortunate souls, with the saloon claiming that 17 people met their end here. Whether every detail of that story is historically accurate is another question, but in Key West, sometimes the legend is almost as entertaining as the history. The tree eventually became part of the building, growing right through the middle of the bar and out through the roof.
Finally, there’s the story of the Lady in Blue, whose ghost supposedly still makes an occasional appearance. So here we were, sitting in a bar with a tree growing through the roof, a tombstone on the floor, and the possibility of a ghost wandering around. At this point, ordering another drink seemed like the safest thing to do. After all, if someone really used the tree for hangings, we figured it had already seen far worse decisions than ours.
Key West Cemetery: Where Even the Tombstones Have a Sense of Humor
We’ve visited our share of cemeteries during our travels, but the Key West Historic City Cemetery is unlike most. In Key West, apparently, even the dead have a sense of humor.
Located in the heart of Old Town, the cemetery covers about 19 acres and dates to 1847. The city established it after an 1846 hurricane damaged the island’s earlier burial ground near the beach. Officials wisely chose higher ground this time. Apparently, even in the 1800s, nobody wanted their final resting place to come with a hurricane evacuation plan. The cemetery now holds approximately 80,000-100,000 graves, 3 to 4 times as many people as currently living in Key West.
Why Are So Many Graves Above Ground?
One of the first things you’ll notice is that many of the graves aren’t underground at all. Instead, you’ll see above-ground vaults, family crypts and elaborate mausoleums. The island’s geology, limited space and high water table made traditional underground burials difficult, so families often placed their loved ones in above-ground vaults. The result is a cemetery that looks quite different from what many visitors expect to see in the United States. Of course we are originally from Louisiana so we are very well acquainted with this scenario.
And then there are the tombstones…
One of the cemetery’s most famous epitaphs belongs to B.P. “Pearl” Roberts. Her gravestone delivers the ultimate I told you so: “I TOLD YOU I WAS SICK.” Well, Pearl, you certainly did. It’s hard not to laugh when you see it, although there’s also something wonderfully human about the inscription. Somebody who knew Pearl well apparently understood that she would have appreciated getting the last word.
Some of the humorous inscriptions:
- Gloria M. Russell “I’M JUST RESTING MY EYES”
- Alan Dale Wilcox “IF YOU’RE READING THIS, YOU DESPERATELY NEED A HOBBY”
- Randy Scott Smith “JUST WHEN THINGS WERE GOING SO WELL”
- Giorgio Aversa “JESUS CHRIST THESE PEOPLE ARE HORRIBLE”
- Patrick Charles Gallagher “I ALWAYS DREAMED OF OWNING A SMALL PLACE IN KEY WEST”
- Angelique Brevard Hoffman “ID RATHER BE IN PARIS”
I agree with Angelique, that would be perfect for mine too. Of course Key West being Key West, it isn’t just the tombstones that makes visitors stop, smile and sometimes pull out their cameras.
Tombstones With Personality
The cemetery contains plenty of unusual names, inscriptions and monuments. Some epitaphs are humorous, some are sentimental, and others leave you wondering about the story behind them. That’s part of what makes wandering through the cemetery so interesting. You’re not simply looking at dates carved into stone. You’re catching little glimpses of the personalities who once called Key West home.
Some stones make you pause because of the person’s accomplishments. Others make you pause because you’re trying to figure out what the family was thinking when they chose the inscription. And that’s really what makes the Key West cemetery different. It feels like Key West.
The island has always attracted independent characters, artists, sailors, adventurers and people who weren’t particularly interested in doing things the conventional way. Somehow, some of that personality survived them and ended up carved into stone.
Otto Family
The Otto family was prominent in Key West, with family members who included doctors, pilots and artists. But what really caught our attention wasn’t the family history—it was who else is buried there. They took the idea of “family” quite literally. Three Yorkshire terriers and a domesticated Key deer named Elfina are buried in the family plot. Elfina even has her own little monument, while the three dogs have individual markers. According to cemetery records, the dogs were Little Boy Otto, Little Derry Otto and Sunny Otto. A pet deer buried in a family cemetery plot? Now that’s something you don’t see every day!
General Abe Sawyer
Then there’s “General” Abe Sawyer, whose grave marker sounds like it belongs to a military hero. Born in 1862, Sawyer stood just 40 inches tall, weighed 40 pounds, and became a well-known performer who traveled with circuses and shows. His nickname, “General,” had nothing to do with military rank. Sawyer had one final request that seems perfectly suited to Key West: he wanted to be buried in a full-size coffin. His friends honored his wishes, giving him a full-sized final resting place despite his small stature.
We couldn’t help but smile at the thought. In a cemetery filled with unusual characters and quirky stories, General Sawyer certainly made sure his final resting place would be just as memorable as his life.
A Cemetery With Chickens?
Of course, this is Key West, so don’t be surprised if your cemetery walk includes a few unexpected visitors. Free-roaming chickens and roosters wander among the graves, and iguanas can sometimes be spotted enjoying the Florida sunshine. At this point, we weren’t sure whether we were visiting a cemetery or attending a very unusual Key West wildlife tour. But somehow, it all seemed perfectly appropriate.
More Than Just Quirky Tombstones
Although the funny epitaphs may be what initially attracted us, the cemetery tells an important story about Key West. They’re only one small part of what you’ll discover here. You’ll find sections associated with different communities and faiths, including Catholic and Jewish burial areas. There are also monuments connected to Cuban independence and veterans of the Spanish-American War, including the USS Maine memorial area.
The USS Maine exploded in Havana Harbor on February 15, 1898, killing more than 260 American sailors and Marines. The disaster became one of the events that helped propel the United States into the Spanish-American War. There are 24 sailors from this disaster buried here.
Finally, the cemetery itself dates to 1847, but its oldest grave marker dates to 1829. The marker belongs to Captain James Johnson, who died on May 8, 1829. He was originally buried in Key West’s earlier burial ground. After the devastating 1846 hurricane destroyed that cemetery and scattered graves and remains, the surviving markers and some remains were moved to the new cemetery on higher ground. So when you stand in front of Captain Johnson’s weathered marker, you’re looking at something that actually predates the cemetery surrounding it by 18 years.
Take Your Time
One of the nicest things about visiting the Key West Cemetery is that you don’t need a ticket or a tour guide to appreciate it. Entry is free. A self-guided map is available at the office or to download on the website, making it easier to locate some of the more notable graves and sections. We recommend slowing down and wandering.
Look at the architecture. Read the names. Notice the dates. Find the unusual epitaphs. And keep an eye out for the chickens and iguanas. You never know what—or who—you’ll discover.
Our Take
The Key West Cemetery isn’t the kind of attraction you necessarily put at the top of your itinerary when planning a trip to the Florida Keys. But that’s exactly why we wanted to include it in our return visit to Key West. We’ve already seen the famous attractions. This time, we were looking for the unusual, quirky and unexpected side of the island.
And where else can you take a peaceful walk through nearly two centuries of Key West history, admire elaborate above-ground crypts, meet a few chickens and come across a tombstone that basically says, “I told you so”? Only in Key West. Sometimes the best travel discoveries aren’t the places everyone tells you to visit. They’re the places that make you stop, laugh, wonder about the story behind what you’re seeing—and then tell everyone back home about it.
The Box: Key West’s Most Ridiculous Photo Op
Just when you think you’ve seen all of Key West’s quirky attractions, along comes The Box. And yes, we’re talking about an actual box. There isn’t a fascinating pirate story behind it, no famous author lived inside it, and nobody important was born here. As far as we can tell, it’s simply a utility box that somehow became worthy of a photograph. Only in Key West!
Naturally, we couldn’t visit Key West without seeing this newest attraction. No, not Hemingway’s house. Not the Southernmost Point. We went to see… a box. Once something becomes a photo opportunity, you can’t just walk past it. You have to get in on the fun.
There are quite a few tongue in cheek 5.0 Google reviews discussing the box’s four sides, galvanized-steel finish, corners, sunlight and nighttime appearance as though they’re reviewing the Louvre.
We couldn’t help but wonder how many ordinary objects around Key West are secretly waiting for their big break. Maybe that trash can over on Duval Street is next.
The best part about The Box? It costs nothing, takes only a couple of minutes, and produces a photograph that will probably generate more questions than any other vacation picture you take here.
Key West Gardens at Fort West Martello: A garden growing through history
One of the best things about returning to Key West is discovering places we somehow missed the first time around. This time, we found a place that combines history, beautiful tropical plants, and a little bit of Key West quirkiness all in one spot.
Key West Gardens at Fort West Martello sits inside the ruins of West Martello, a Civil War-era fort overlooking the Atlantic. Construction began during the Civil War, but the fort never saw battle and was never fully completed. Over the years, much of the abandoned structure became a convenient source of building materials for Key West. Thankfully, someone eventually realized that perhaps tearing down an old fort wasn’t the best idea!
In the 1950s, the Key West Garden Club stepped in and began transforming the ruins into the tropical garden we see today. What could have been another forgotten military structure became a lush garden filled with palms, orchids, tropical plants, and winding paths tucked among the old brick walls.
And that’s what makes this place so interesting. You aren’t simply walking through a garden. You’re walking through the remains of a Civil War fort while tropical vegetation grows around and over the historic walls.
We loved the combination of history and nature. One minute you’re admiring an orchid, and the next you’re looking at a centuries-old-looking brick wall and wondering what this place must have looked like when soldiers occupied the fort.
Best of all, admission is free, although donations help the Garden Club maintain this beautiful little oasis.
How did we miss this on our first trip? That’s one of the great things about Key West. Just when you think you’ve seen it all, you turn a corner and discover something completely different. A Civil War fort turned tropical garden? Only in Key West!
The African Cemetery at Higgs Beach: A Story Key West Should Never Forget
Not every place we discovered on our return to Key West was quirky or funny. Some are important because of the history they preserve. One of those places is the African Cemetery at Higgs Beach, a memorial honoring hundreds of Africans who died in Key West after being rescued from slave ships in 1860.
In the spring of that year, the U.S. Navy intercepted three American-owned ships—the Wildfire, William, and Bogota—that were transporting 1,432 Africans to Cuba, where they were to be sold into slavery. Instead, the ships were brought to Key West. The local community provided food, clothing, shelter, and medical care to the survivors. Even with that help, 294 people died during the 85 days they spent in Key West. They were buried near the southern shore of the island.
For many years, the burial ground was largely forgotten. Then, in the 1990s, historian Gail Swanson began uncovering clues about what had happened there. Archaeological surveys later used ground-penetrating radar to identify rows of graves without disturbing the burials. Additional surveys eventually located many more graves.
Reflections today
Today, the memorial uses African symbols, artwork, and plaques to tell their story and honor those who died. Located near Higgs Beach and West Martello, it gives visitors a chance to pause and remember a part of Key West history that could easily have disappeared.
Standing here gave us a very different perspective on Key West. We had returned expecting to find more unusual attractions, restaurants, and places we had somehow missed. Instead, we found a story that reminded us that travel isn’t always about discovering something new and fun. Sometimes it’s about discovering a story that deserves to be remembered.
And this is one of those stories. The African Cemetery at Higgs Beach is recognized as the only known cemetery in the United States where African refugees rescued from the transatlantic slave trade are buried.
Key West AIDS Memorial
Next to the African Cemetery at Higgs Beach, we found the Key West AIDS Memorial. We weren’t really looking for another stop; we were still thinking about what we’d just seen. Then we came upon the Key West AIDS Memorial. It caught us a little off guard.
I have to admit, I wasn’t prepared for how personal it would feel. We took a moment to stand there quietly and sadly remember many of our own friends who lost their lives to AIDS, as well as the people we know and love who are living with HIV. Reading the names on the memorial brought back memories of people who should still be here today—their laughter, their personalities, the good times we shared, and the empty spaces they left behind.
For a moment, the sounds and energy of Key West seemed to fade into the background.
Here we are in a place we usually associate with sunsets, chickens, colorful characters, and finding the next slice of Key lime pie, and suddenly we are standing in another place of remembrance. The two memorials tell very different stories, separated by more than a century, but both made us stop and think about the people behind the names.
Maybe that’s what struck me most about returning to Key West. On a second visit, you have time to look beyond the obvious attractions. You start noticing the stories that aren’t always on the front of the brochure. And standing there beside the water, reading those names and listening to the waves, Key West felt a little different—not less fun, but more real.
Some places make you laugh. Some make you take a picture. And some make you stop for a moment, remember the people you’ve lost, appreciate the people still in your life, and simply be grateful. This was one of those places.
To wrap up our week
Whether you’re visiting for the first time, celebrating your birthday, or simply returning for another adventure, we think Key West offers something special for everyone. From the lively atmosphere of Duval Street, beautiful historic sites, heartfelt memorials to unforgettable sunsets and world-famous Key lime pie, it’s easy to see why so many people return year after year.
If you’re planning a Florida Keys vacation, put Key West at the top of your itinerary. Bring comfortable shoes, a camera, an appetite, and plenty of time (don’t forget the sunscreen, bug spray and cortisone cream too)—you’ll discover that the best memories often happen when you simply wander and enjoy the island’s laid-back charm.
Just don’t be surprised when at the end of your visit, you’ll probably have just as many chicken photos as sunset pictures. They are great at photobombing you.
See you on our next adventure!