There are some trips to Key West where you arrive with a color-coded itinerary, dinner reservations, tour times and a plan for every hour.
And then there are the trips where you basically say, “We know where we’re having dinner tonight. We’ll figure out the rest.”
This trip was definitely closer to option number two.
Kevin and I headed back to Key West for a few days of wandering, eating, exploring, catching live music, trying a few new places and revisiting some old favorites.
And honestly?
Those are sometimes the best Key West trips.
We stayed somewhere new, found a restaurant that immediately landed on our return list, rediscovered a few attractions we hadn’t visited in years, rode around the island, ate a LOT of seafood and somehow managed to find even more places we hadn’t tried before.
Which is exactly why Key West never gets boring.
Here’s how the trip went.
First Stop: Conch Republic Seafood Company
We have traditions when we arrive in Key West.
One of them is eating at Conch Republic Seafood Company.
Depending on what time our flight arrives, it may be our first lunch or our first dinner, but sooner or later we usually end up sitting at the bar overlooking the marina.
And yes, we are bar people.
Not necessarily because we’re there to drink all night, but because some of the best conversations happen when you sit at a restaurant bar.
You meet bartenders.
You meet locals.
You meet travelers from Arkansas who are considering buying a condo in Key West.
You meet people who arrived with absolutely no plan whatsoever.
Basically, you never know who is going to sit down next to you.
On this particular night, Kevin ordered a mahi fish sandwich and we had some Key West pink shrimp, which are always one of our favorites.
Then the conversations started.
One couple had driven through the Keys and was in town for Lobsterfest. Another was basically winging the entire vacation.
And that became one of the themes of this trip.
You really can wing Key West.
I do have one little piece of advice, though.
If there is something you absolutely want to do, especially fishing, snorkeling or anything that depends on the weather, schedule it toward the beginning of your trip.
That way, if Mother Nature decides to rearrange your plans, you have time to reschedule.
Everything else?
Wander a little.
You might be surprised where you end up.
Friday Night Means the Green Parrot
After dinner, we wandered over to one of our favorite Key West dive bars, the Green Parrot.
No fancy food menu.
Popcorn? Yes.
Great live music? Absolutely.
We walked in, ordered drinks, sat down and naturally the band announced they were taking a break.
Apparently, this was our special talent on this trip.
Walk into a bar.
Find the live music.
Watch the musicians leave for 20 minutes.
We somehow managed to do this more than once.
Luckily, we eventually caught some of the music, and the Green Parrot remains firmly planted on our must-stop list.
We Stayed at La Concha This Time
One thing we try to do is stay somewhere different on many of our Key West trips.
It gives us a chance to experience different parts of the island and, more importantly, report back to you about what we liked and what we didn’t.
This time we stayed at La Concha Key West.
Let’s start with the biggest positive.
The location is fantastic.
You step outside and you’re right on Duval Street.
Irish Kevin’s, Sloppy Joe’s, shops, restaurants, bars and live music are all right there.
If being in the middle of everything is important to you, the location is hard to beat.
La Concha is also part of Marriott, so that may be a plus if you collect Marriott points or rewards.
The hotel had live music while we were there, and one night the lobby/bar area was absolutely packed. People were dancing and having a fantastic time.
There was just one thing we really missed.
Outdoor space at night.
We’re used to staying in historic inns and smaller properties where we can sit outside in the morning with coffee or come back after wandering Duval and sit on a porch or patio.
La Concha has a nice pool and outdoor area, but we discovered that space wasn’t accessible later in the evening.
For us, that was probably the biggest downside.
Would I tell someone not to stay there?
Absolutely not.
If you’re coming for a few nights, want a central location and don’t care about having quiet outdoor space at night, put it on your list.
For us?
I think we may drift back toward the historic inns next time.
Kaya Eats Was One of Our Biggest Surprises
You know those places you’ve walked past dozens of times and somehow never tried?
That was Kaya Eats for us.
From Duval Street, it looks fairly small.
Then you walk inside.
And it keeps going.
There’s much more space in the back, live entertainment, pinball machines and even karaoke.
We originally stopped in for breakfast.
They serve breakfast on Saturdays and Sundays, and we practically had the place to ourselves.
Kevin ordered the breakfast special, the coffee was good, and even the water stood out because it was flavored with cucumber and mint.
Our waiter told us we needed to come back for the fish.
So we did.
Kevin tried the snapper sandwich, which had tons of flavor and quickly moved Kaya onto our “why have we never eaten here before?” list.
That’s your reminder not to judge a Key West restaurant by how crowded the front doorway looks.
Sometimes everybody else is just standing in line at one of the places already on every Top 10 list.
A Visit to Key West Island Books
Of course, I had to stop at Key West Island Books and visit Suzanne.
If you’re part of the Fun in Key West Book Club, there is a whole section devoted to our book picks.
And here’s a little insider secret.
Suzanne has the entire list for the rest of 2026.
I normally don’t announce each book until right before the new month begins.
So technically, you could stroll into Key West Island Books and get a sneak peek.
I may need to start hanging out there more often because we even picked up a few new book club members while we were visiting.
There are worse places to spend an afternoon than tucked inside an independent Key West bookstore.
Lobsterfest Was Bigger Than We Expected
We happened to be in town during Key West Lobsterfest, and I have to say, I didn’t realize how big it would be.
There was lobster everywhere.
Food vendors.
Craft vendors.
People wandering Duval.
Music.
And more lobster.
The event continued well into the evening and had much more going on than I expected.
If you love festivals and Caribbean spiny lobster, this is definitely one to keep on your future August travel radar.
We Revisited the Mel Fisher Maritime Museum
It had probably been five to seven years since we last visited the Mel Fisher Maritime Museum, so we decided it was time to go back.
And Kevin summed Mel Fisher up perfectly.
He deserves the Persistence Award.
The story of how long he searched for treasure, the sacrifices involved and the years spent following clues is almost as interesting as the treasure itself.
Then you see the gold.
The coins.
The emerald jewelry.
Items that sat underwater for centuries and somehow still look incredible.
Even if you’re not normally a museum person, Mel Fisher’s story is such an enormous part of Key West history that I think the museum is worth experiencing at least once.
And if you’re traveling with older kids or teenagers, there’s enough treasure, shipwreck history and adventure here to keep things interesting.
Red Shoe Bistro Went Straight Onto the Return List
And now we need to talk about one of the best surprises of the entire trip.
Red Shoe Bistro.
This restaurant is small.
Very small.
If you want a table, I strongly recommend making a reservation.
Naturally, we did not.
That would require a level of planning we apparently were not doing on this trip.
But remember how I said we’re bar people?
There were two seats available at the bar.
Perfect.
We ordered the tiny bread with a whipped butter, goat cheese and dill spread.
Then deviled eggs topped with scallops.
Then yellowtail snapper and hogfish.
Everything had layers of flavor.
But somehow dessert managed to steal the show.
Lavender cheesecake.
I wasn’t convinced.
Lavender desserts can sometimes taste a little too much like you wandered into the soap aisle.
This did not.
It was one of the best desserts I’ve had.
Kevin gave Red Shoe Bistro a full five-star rating.
And yes, it is absolutely going back on our list.
Three Classic Key West Tours
We also spent part of this trip revisiting three classic Key West tour experiences.
Conch Tour Train
I call the Conch Train the Jungle Cruise of Key West.
If you’re a Disney fan, you probably understand exactly what I mean.
There are stories.
History.
Corny jokes.
Different guides add their own personalities.
And somehow, even when you’ve heard some of the stories before, it’s still fun.
One important thing to know is that the Conch Train is no longer hop-on, hop-off.
You stay aboard for the tour through Old Town.
Also, if there’s a major festival happening and Duval Street is closed, you may want to choose another day because the route can be affected.
Old Town Trolley
If you do want a hop-on, hop-off experience, this is where the Old Town Trolley shines.
The trolley covers a much larger portion of Key West, including areas away from Old Town.
You can ride out toward North Roosevelt Boulevard, hop off near attractions and beaches and use it as transportation while learning about Key West along the way.
We even hopped off near the Hampton Inn because Kevin wanted to check out the property.
Naturally, we found the tiki bar.
And naturally, we met people.
Again, this is why we like sitting at bars.
The trolley is particularly useful if you fly into Key West without renting a car but still want to explore more of the island.
Ghosts & Gravestones
Then we switched gears after dark with Ghosts & Gravestones.
This one isn’t necessarily a jump-out-and-scare-you ghost tour.
It’s more storytelling.
Strange history.
Haunted tales.
Places around Key West connected to those stories.
You also get to visit part of the Shipwreck Museum after dark, which was fun because several people on our tour decided they wanted to return and see the whole museum during the day.
If you love history with a slightly spooky twist, this can be a fun nighttime option.
Want to Try One of These Tours?
You can learn more about the Conch Tour Train, Old Town Trolley and Ghosts & Gravestones here:
funinkeywest.com/conch
Use promo code 7219.
There’s about a $3-per-person savings built into the online booking depending on the tour.
Hey, three bucks is three bucks.
That’s practically the beginning of a Key West bar tab.
This is an affiliate link, which means I may earn a commission when you book through it at no additional cost to you.
One of My Favorite Hemingway House Experiences
We also had a chance to spend some time at the Ernest Hemingway Home and Museum before things got busy.
And one of my favorite parts wasn’t even inside the house.
It was the garden.
There’s something completely different about the Hemingway Home early in the day when the gardens are quiet and the cats are wandering around.
You could easily grab a coffee nearby, come inside, find a bench and just spend a little time sitting in the garden.
There’s no need to rush through.
I think both the Hemingway Home and Audubon House have this wonderful hidden benefit that people sometimes overlook.
Yes, you’re there to see the historic house.
But the garden itself can be part of the experience.
Bali Bar: Hidden Just Steps From Duval
Another place I love is Bali Bar.
You walk through a little hidden alley surrounded by tropical greenery and suddenly it opens into a relaxed tiki-style bar with live music.
And somehow, even though you’re steps away from Duval Street, everything feels quieter.
More relaxed.
A little tucked away.
Those are often my favorite Key West places.
The ones hiding just around the corner from the chaos.
The Piña Colada You Told Me to Try
Sometimes the best recommendations come from you.
I had asked about great Key West cocktails, and several people told me to try the piña colada at Key West First Legal Rum Distillery.
You were right.
Fresh ingredients.
Real pineapple.
Rum.
Rum floater.
Yes, please.
This officially landed on the recommendation list.
Doing Work Coffee Deserves a Morning Stop
If you’re wandering near Duval and Eaton in the morning, stop by Doing Work Coffee.
Daniel is a micro-roaster, and one of the really interesting things he does is age coffee beans in rum barrels from the nearby distillery before roasting them.
The result isn’t a sugary rum-flavored coffee.
It has these subtle notes from the barrels that make it really interesting.
He also sources his coffee carefully and makes fresh baked goods.
We had a cinnamon roll made with fresh Georgia peaches that was fantastic.
Coffee + fresh pastry + Key West morning.
That combination works.
And Then There’s Wicked Lick
Same place as Doing Work Coffee is Wicked Lick, where the ice cream is made using liquid nitrogen.
If you happen to walk by while they’re preparing batches, you may see clouds of vapor billowing around the shop.
Come back when they open for ice cream and grab a scoop.
Because apparently breakfast pastries followed by ice cream is an acceptable Key West itinerary.
I don’t make the rules.
Don’t Forget Caroline Street
One restaurant Kevin wanted to make sure we mentioned was Square Grouper on Caroline Street.
This is another reminder that there’s a lot more to Key West dining than Duval Street.
The food was excellent, and they also have a little raw bar area in the back.
If you spend your entire trip walking only up and down Duval, you’re missing a big part of Key West.
Walk Caroline.
Walk Fleming.
Walk Elizabeth.
Look at the historic homes.
Peek down the side streets.
Take photos.
Get a little lost.
That’s where some of the best Key West moments happen.
So What Was Our Favorite Part of This Trip?
That’s nearly impossible to answer.
Kevin’s top picks included:
Conch Republic Seafood Company.
The Green Parrot.
And simply wandering at night, following the sound of live music from place to place.
Mine?
The peaceful gardens at the Hemingway Home.
The hidden feeling of Bali Bar.
That fantastic piña colada at First Legal Rum.
And I’m sneaking Doing Work Coffee onto my list too.
But I think what really stood out was how many new things we still found.
We’ve been to Key West many times.
And there are still restaurants we’ve never tried.
Museums we haven’t visited in years.
Historic houses I want to explore more deeply.
Small businesses with stories we haven’t heard yet.
That may be the biggest reason we keep coming back.
Key West isn’t something you check off a list.
You experience one little piece of it.
Then you come back and discover another.
Planning Your Own Key West Trip?
There’s nothing wrong with winging part of your vacation.
Actually, I recommend leaving some room for it.
Schedule the things that truly matter to you, especially activities that could be affected by weather.
Then leave yourself some blank space.
Walk down a street you haven’t explored.
Try the restaurant you’ve walked past three times.
Sit at the bar.
Talk to the person next to you.
Ask a small business owner how they ended up in Key West.
Follow the live music.
You never know where the day is going to take you.
And that’s kind of the point.
If you need help planning a Key West getaway, cruise, Alaska trip or another adventure, Kevin can also help through Out A Here Travel.
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And for more Key West restaurants, history, things to do, cocktails, trip planning and island rabbit holes, keep exploring right here at Fun in Key West.
