Thanksgiving in Key West — Just Not the Way I Planned

Key West had already become a special place for me. Last year’s Thanksgiving trip left me looking forward to going back, but this time the road there was a little different.

Sometimes the best trips are the ones that don’t go exactly according to plan.

The plan was simple:

Travel south in the RV.
Spend Thanksgiving with my family.
Enjoy another Key West adventure.

Of course, the RV had other ideas.

But even with an unexpected detour, the adventure continued.

When the Plan Changed

When I left home, I expected this trip to look a lot like the previous one.

The RV would be my home base. Bandit would be my travel companion and we would make our way south at our own pace.

Instead, the RV ended up waiting at the dealership in Chattanooga while Bandit and I continued on by Jeep.

By the time Bandit and I arrived at my parents’ house in Flagler Beach, the next decision was how to handle the Key West portion of the trip.

Originally, the plan had been for all of us to go together.

But after thinking through the logistics of traveling by car and staying in hotels, Mom decided that part of the trip wasn’t the right fit for her.

And honestly, that was okay.

She stayed home with Bandit, and Dad and I continued on for our own adventure.

I loved that Bandit got some extra grandma time…

and I got some unexpected one-on-one time with my dad.

Back to Key West

Dad and I made our way south and settled in at Trumbo Point on the Key West Naval base. The view from where we stayed was pretty amazing.

One of my favorite things about returning somewhere is that it feels both familiar and new at the same time.

Some things you recognize. Some things surprise you.

And sometimes the best memories come from the moments you didn’t plan.

Thanksgiving in Key West

But the most important part of the trip was Thanksgiving itself.

A table full of food. Family gathered together. Five people enjoying time together.

No matter where you are, there is something comforting about sitting around a table with people you love.

Time With Dad

The best memories from this part of the trip weren’t necessarily the places we visited.

They were the simple moments.

On Friday, Papi and I met up with my cousin and her husband at Two Friends Patio Restaurant for live music and lunch. Somewhere between the drinks and the conversation, I ended up with a cocktail umbrella tucked behind my ear — which felt about right for Key West.

Later that same afternoon, after Papi patiently waited through my shopping trip, we stopped at The Stoned Crab for a drink to recover.

Sometimes travel gives you experiences. Sometimes it gives you time.

And sometimes it gives you both.

A Taste of Home

Of course, food is always part of any good trip. And sometimes the meals that stand out are the ones that connect you back to home.

We stopped at El Jibarito near Miami — a fun connection for me because of my Puerto Rican heritage.

Finding little pieces of culture and home while traveling is always special.

Somewhere along the way, we passed the Guitar Hotel at the Seminole Hard Rock Hotel & Casino — one of those landmarks you can’t miss from the highway, even without stopping.

Exploring Key West

The best part of Key West isn’t always the big attractions. Sometimes it is just walking around and seeing what you find.

I spent time at Smathers Beach, watching pelicans, birds, and jellyfish.

I walked along the shore. I put my feet in the water.

I found a beach set up for a wedding. I just enjoyed being there.

And then there were the iguanas.

So many iguanas.

Walking around Trumbo Point and the surrounding areas, I found wildlife, bridges, roosters, and plenty of reminders that Key West is unlike anywhere else.

There were also some fun Christmas displays that made me smile.

Back With Bandit

Eventually, it was time to head back.

After spending time exploring Key West with Dad, it was good to be back with Mom and Bandit again.

Before heading home, Bandit and I got one more Florida adventure. A walk along Flagler Beach.

After all the changes this trip had brought, slowing down for a walk on the beach felt like the perfect ending.

One More Feast Before Home

Before heading home for good, there was one more Flagler Beach tradition to squeeze in.

Catching crabs. Cooking crabs. Cracking crabs at the counter with a mallet and way too many napkins.

It’s not glamorous, but it might be one of my favorite kinds of afternoons — messy, simple, and always better with family.

The RV Was Still Waiting

Before heading home, I stopped back by Chattanooga to check on the RV.

It was still sitting at the dealership.

The trip definitely did not go the way I originally planned.

The RV didn’t make it to Florida. The route changed. The schedule changed.

But the important parts of the trip still happened.

I got another Thanksgiving in Key West.

I got time with my dad. I got family memories.

And Bandit and I still found a way to make the most of the adventure.

So I guess Chattanooga and I aren’t done with each other yet.

I’ll be back — hopefully this time to pick up the RV and bring it home!

Sometimes the best adventures aren’t the ones where everything goes perfectly.

Sometimes they are the ones where you learn how to enjoy the journey anyway.