As promised, I’m doing a deep dive recap of our recent trip. But let’s be honest—this wouldn’t be a complete, absolutely wonderful recap without including my husband Kevin, who is the brains behind Out A Here Travel.
We just got back, and I have thoughts. From navigating new airport terminals to discovering breweries tucked away on Front Street, this trip was a mix of our die-hard favorites and some surprising new finds.
Whether you’re a Key West regular or planning your first pilgrimage to the Southernmost Point, grab a drink (preferably something with rum in it), and let’s break down everything we learned on this trip.
Escaping Pittsburgh: The New Airport Experience
We flew out of the new Pittsburgh International Airport, and if you haven’t flown out of there since mid-November, you are in for a shock to the system. The tram? Gone.
We’re so used to the old routine: park in extended, take the escalator, ride the tram, hit the old terminal. Not anymore. Now, shuttle buses sweep you right to the front of the new terminal. You just walk right in.
And here is the kicker: the TSA experience has totally changed. With the new technology, you don’t have to take your shoes off. You don’t have to take your laptop out of your bag. You just stroll through. It was fast, easy, and honestly, started the trip on a high note because nobody likes hopping on one foot trying to put a sneaker back on while holding a boarding pass in their teeth.
Landing in Paradise: The Key West Airport Makeover
We snagged a direct flight from Pittsburgh to Key West (highly recommend), and the arrival experience was… different.
If you’ve been to Key West before, you know the drill. You used to walk down the stairs onto the tarmac, feel that humidity slap you in the face, walk across the pavement, and try to snag a selfie with the “Welcome to Key West” sign while ground crew yelled at you to keep moving. It was chaotic, hot, and charming in a “we’re definitely on an island” kind of way.
Well, we are hitting the big time now, folks.
You no longer walk across the tarmac. You now walk through these glass walkways—I call them “gerbil tubes”—that are air-conditioned and full of windows. It dumps you into a main concourse that now has eight gates instead of the original four. It’s significantly larger, but don’t worry, it hasn’t lost all its small-town charm. You still go down the escalators to grab your bags and find ground transportation.
Pro Tip on Ground Transport:
Don’t bother with Uber or Lyft when you land. Just walk out to the taxi stand. There is a line of taxis ready to go. It costs about $18-$20 to get to the Southernmost area (prices are by zone), and it’s just as fast, if not faster, than waiting for a ride-share to navigate the loop.
The Resort Surprise: Southernmost Beach Resort
We decided to switch things up this time. We usually stay at small B&Bs to get that local, intimate vibe. I admit, I was hesitant about booking the Southernmost Beach Resort. I was worried it would feel too stuffy or corporate.
I was wrong. (Don’t tell Kevin I said that).
I was pleasantly surprised. It has a total all-inclusive feel without actually being an all-inclusive. The complex is huge—six acres spanning three blocks—with three pools, a private beach, and that famous pier you see in all the photos.
The Vibe:
It was seamless. We checked in and were immediately put into a text message queue. This was brilliant. They texted us updates on daily activities—trivia games, conch shell blowing contests (which we missed, tragic), and even a rum runner making class.
We had a situation where a wedding was happening on the property, and they texted us ahead of time: “Hey, the beach area by the cafe will be closed for a wedding for Brandon and Lauren.” They even gave us the couple’s names, so instead of being annoyed that the beach was closed, we felt like we were part of the celebration.
Sunrise Magic:
We had a room with a balcony and a partial ocean view, which was killer. But the real magic was the inclusivity of the resort. You know that pier that juts out into the ocean? It belongs to the resort. We walked out there in the morning, and there were people in their bathrobes with cups of coffee, just sitting there watching the sunrise. It felt so relaxed and private.
At night, because you’re at the southern end of the island away from the neon lights of Duval, it gets dark. We walked out and could actually see the stars. You could see shrimp boats way out in the distance. It was a level of quiet beauty I didn’t expect from a larger resort.
The Food & Drink Scene (Priorities, People)
Obviously, we didn’t just sit in the room. We hit the ground running—or eating.
The Fish Sandwich Requirement
Our first stop, like clockwork, was the Southernmost Beach Cafe. We arrived around 2:00 PM, starving, and ordered the fish of the day sandwich.
This wasn’t a sad little filet. This thing was massive—like, inch-thick fresh fish filling up the entire bun. It’s consistent, it’s fresh, and sitting there watching the waves while eating seafood is the only way to start a trip.
The Coffee Situation
You all know I need my caffeine. We noticed way more coffee options this trip than in the past.
- Southernmost Beach Cafe: They have a great little coffee bar in the morning. Instead of standing in a massive line at Anna’s across the street (which is great, don’t get me wrong), we zipped into the cafe, grabbed coffee, and sat by the ocean.
- La Grignote: We walked past this bakery on Duval across from Banana Cafe every morning, and the smell of pastries was intoxicating. They tout themselves as the biggest bakery in Key West. It was packed every single morning.
- Black Rifle Coffee: Located right at Truman and Duval. Kevin loves their zero-sugar energy drinks.
New Find: Southernmost Brewery
This place opened almost two years ago on Front Street (tucked back where the old Rum Barrel used to be), and we finally stopped in.
It’s a cool spot. They brew small batches right there in the back—literally a one-barrel system. They had about 8 or 9 beers on tap. Kevin had a Scotch Ale (which is rare to find and he loved it) and I… well, I am not an IPA girl. I am not “hoppy.” But they had seltzers and other options, plus a nice outdoor space with cornhole. It’s shaded, so if it’s blazing hot, you can hide out there.
The “Secret” Key Lime Pie
We took a tour—more on that in a second—that included a lunch stop with a slice of Key Lime Pie. This wasn’t your standard pie. The crust had a specific flavoring I hadn’t tasted before.
The restaurant is a place we usually only go to for breakfast. We had never considered it for lunch or dinner, and certainly not for pie. I’m not going to spoil the location (you have to take the tour!), but let this be a lesson: if you love a place for breakfast, go back for dinner. The menu might surprise you.
Activities: Beyond the Bar Stool
We didn’t just eat and drink. We did some actual exploring.
iWitness Crime Tour
We hopped on the iWitness Crime Tour hosted by Kim. If you know Key West, you know there are about a million tours. This is different.
It’s a 90-minute walking tour, but you only cover about six blocks, so it’s very accessible. Kim has done deep research into the crimes of Key West—not super gruesome stuff, just the interesting, scandalous history you haven’t heard a thousand times before. She is a master storyteller. If you want a break from the ghosts but still want the history, this is the one.
The Cemetery Walk
I know getting excited about a cemetery sounds a little morbid, but the Key West Cemetery is fascinating. It’s actually not in its original location—the “Great Havana Hurricane” years ago uprooted the old one, so they moved it to the highest point in Key West (a staggering 16 feet above sea level, maybe).
We did a full walk-through. It’s full of history, quirky headstones, and iguanas. You’ll see names of the founding families that you recognize from street signs. It’s peaceful and incredibly interesting.
People Watching at The Whistle
Is the balcony at The Whistle terrifying? Yes. Do I question the structural integrity every time I sit there? Also yes. But is it the best people-watching spot on Duval? Absolutely.
We sat up there, met a fifth-generation Conch (local), and just watched the chaos of the street below. It’s a bucket list item for a reason.
A Few Heads-Up Items for Travelers
If you haven’t been to the island in a year or two, here are a few logistical changes we noticed:
- The Southernmost Buoy: It has moved! The foundation of the original spot is eroding, so they are doing repairs. They’ve moved a replica buoy (slightly smaller) to a location near the Southernmost Beach Cafe for photos.
- Kermit’s Key Lime Pie Shop: The shop on Elizabeth Street was sold to a corporate company out of Savannah a couple of years ago. The vibe has changed. The koi pond is now seating, there are fewer tastings, and it feels a bit more… corporate.
- The Duval Loop: Rumor has it that funding changes mean the free Duval Loop might be transitioning to a paid or on-demand service in the coming years (around 2026). For now, check the City of Key West app for the latest “Ride on Demand” options.
- Departure Warning: When we flew out around 11:30 AM, hardly anything was open at the airport. The Conch Flyer, the newsstand and Starbucks (which had a line to the moon). Also, there are only one or two baggage carousels. If you are landing, grab your bag before you get coffee. They pull the bags off the belt fast.
Kevin’s Corner: Out A Here Travel
A quick shoutout to my better half. We started Out A Here Travel back in 2018, paused during the pandemic (because, obviously), and are back in full swing.
Kevin specializes in travel for the 50+ crowd—empty nesters, retirees, or just people who want a grown-up vacation. He’s focusing heavily on:
- Alaska Cruises & Land Tours: Since we lived there, he knows the good spots.
- Ireland: Always a favorite.
- Orlando: We have a house there, so we know the parks inside and out.
- Small Ship Cruising: We saw the American Cruise Lines ship in port—less than 200 people, all balcony rooms. It’s perfect if you hate the mega-ships.
If you are overwhelmed by planning, just reach out to him. He loves putting together itineraries so you can just show up and enjoy the cocktail.
Leaving the Island
Leaving Key West is always the hardest part. But honestly, this trip refreshed my love for the island.
Despite the changes—the new airport tubes, the corporate pie shops—the vibe remains the same. It’s friendly. It’s relaxed. It’s a place where you can watch a sunrise in your bathrobe on a pier, listen to a country singer in a bar with a sandy floor (shout out to the Tipsy Rooster!), and eat the best shrimp of your life at Conch Republic Seafood Company (Happy Hour, get the Reds, thank me later).
Until next time, keep living that island life, even if you’re just in your living room.
