Some trips are relaxing.
Some trips are productive.
And then there are the trips you know you’ll be talking about for years.
Our recent trip to the Florida Keys was definitely one of those.
Between giant tarpon, goliath grouper, rough offshore seas, boat problems, wildlife encounters, and nonstop laughs with friends, this trip turned into one of the most memorable adventures Harriet and I have ever had together.
Finally Back in the Keys
The moment we made it down to the Keys, it felt like a weight lifted off our shoulders. Between work, school, life, and trying to grow The Diabetic Travel Guide, we needed this trip badly.
The Keys have always felt different to us. Slower. Simpler. More peaceful.
We spent time around Hawks Cay, explored different areas, enjoyed the water, and started documenting more of the trip than we ever have before. We took photos, videos, and even started filming small vlog-style clips together for future content.
Honestly, it felt exciting to finally start creating the kind of content we’ve talked about making for a long time.
Harriet’s Tarpon Battle
One of the biggest moments of the entire trip happened on day two.
Harriet hooked into an absolute giant tarpon that our guide estimated around 120 pounds.
What followed was over an hour of chaos, excitement, exhaustion, and adrenaline.
Watching her fight that fish was incredible. Every run felt powerful, and every time we thought the fight was slowing down, the tarpon would explode again.
Eventually, we got the leader touch.
We were seconds away from landing this fish.
And then… the hook pulled.
The fish swam away.
As heartbreaking as it was in the moment, it immediately became one of those memories we knew we’d never forget. Honestly, that fight alone made the trip worth it.
At one point during the tarpon fishing, a massive nurse shark — probably around six feet long — casually swam right up beside the boat with its head partially out of the water like it wanted to join the trip too.
Naturally, instead of making smart decisions, I ended up sitting there petting a wild shark while everyone laughed at me.
Honestly, moments like that are part of what makes the Florida Keys feel so wild and unforgettable.
Goliath Grouper, Mangroves, and “The Coffin”
The next few days brought a completely different kind of fishing.
Instead of tarpon, we spent time targeting structure fish and ended up catching multiple goliath groupers — including an awesome fish Harriet caught back in the mangroves that was estimated around 50 pounds.
Fishing around structure like “The Coffin” kept things exciting all day long. Every drop felt like something big could happen.
Some fish won. Some fish didn’t.
But the best part of those days honestly may have been the laughs.
Our friends Jack and Sam joined us for part of the trip, and there were plenty of moments that had us crying laughing on the boat and at dinner afterward.
One of the funniest moments happened during Jack’s birthday dinner when Harriet used ChatGPT to turn a photo of Jack and me into old grandpas. Somehow it looked WAY too realistic.
Harriet and Sam were laughing so hard they could barely breathe while Jack and I sat there wondering why we suddenly looked 85 years old.
That photo may honestly live forever now.
Offshore Chaos
Our final offshore fishing day turned into an adventure none of us expected.
We booked an offshore trip hoping for mahi, tuna, and whatever else the ocean wanted to give us. The weather was rough, but we were committed to going.
Not long into the trip, the center engine’s lower unit failed.
For a moment, we genuinely thought the day might be over before it even started.
Thankfully, after some scrambling and a boat swap, we were able to continue the trip.
The seas stayed rough all day, and Sam started getting seasick, but thankfully she had Zofran with her and powered through it like a champ.
Eventually, things started turning around.
We caught blackfin tuna, smaller mahi, saw sea turtles, stingrays, and even spotted a massive great white shark during the trip.
Even though it wasn’t the easy offshore day we imagined, it somehow made the experience even more memorable.
Why Trips Like This Matter
This trip reminded us why we started The Diabetic Travel Guide in the first place.
Life gets busy. Work gets stressful. Diabetes adds extra planning and challenges to travel sometimes.
But experiences like this remind us that adventure is still possible.
Some of the best memories come from the imperfect moments:
- the fish that got away
- the rough days offshore
- the unexpected problems
- and the moments you can’t stop laughing about afterward
Those are the stories that stick with you.
And honestly, we’re already counting down until the next trip back to the Keys.
Special thanks to Captain Josh Benton with Spartina Guide Service and Captain Mike Diaz with Pelagic Raptors!
3 Comments
Great fishing!
what a great story!! Beautiful Pictures!!!
Thank you!!!