Always Up: Quiet Miles

I booked this trip six days before takeoff.

That alone tells you where my head was.

A conversation with friends the weekend before put Trinidad back on my radar. One was from there. Another had family ties. Carnival was coming. I already had the dates blocked off. I checked flights.

They weren’t disrespectful.

So I booked.I didn’t come to Trinidad to collect moments.
I came to let a few days pass without asking anything from them.

The Decision

I didn’t know much about Trinidad beyond the obvious. Culture. Music. Carnival energy.

What I did know was this:

  • It was warm
  • It was new
  • The flight wasn’t ridiculous

Sometimes that’s enough information for a decision.

I didn’t even realize I was arriving at the start of Carnival until later. In hindsight, that explained why everyone boarding the plane looked like they were on their way to have the time of their lives.

I, meanwhile, was on my way to mind my business.

The Booking Logic (and the First Mistake)

I chose the Hyatt Regency Trinidad over Brix after reading reviews. Not because I love hotel chains, but because I love knowing what I’m walking into.

Predictability is underrated.

I arranged hotel pickup for thirty dollars. Trinidad doesn’t have Uber, which already had me slightly annoyed before landing, but I decided to be flexible. Growth and all that.

The Flight (A Series of Small Humblings)

I fly American. Platinum. Group 3. Window seat. Headphones on. I board with intention.

Except this time.

I assumed boarding would be normal. Grab food. Stroll to the gate. Sit down like an adult who’s done this before.

Wrong.

By the time I cleared security, boarding was in ten minutes. Not thirty. Ten.

So now I’m power-walking through the airport, hungry, annoyed, and confident that I’ll at least get food on the plane.

At the gate, I discover I need to fill out a paper arrival form. Paper. In 2026.

That small delay bumps me out of Group 3. I board later than planned and land around row eighteen.

If you’ve flown enough, you know what that means.

They’re running out of food.

And they did.

When the flight attendant told me all they had left was fruit and hummus, I stared at him like he personally decided this.

I took the cookie and accepted my fate.

The couple sitting next to me noticed immediately. Older. Warm. Clearly Trinidadian. The kind of people who ask real questions and actually listen to the answers.

They offered me food. I declined at first because pride is a real thing. Then we started talking.

They were heading home for Carnival. Renting a car. Already had plans. They offered to drive me around while I was there. The wife casually mentioned I should meet their nieces and nephews and hang out.

It was one of those moments where travel reminds you that most people are decent.

Later, the flight attendant came back holding a turkey club like it was a golden ticket. The woman next to me immediately told him, “He better not be paying for that.”

I wasn’t.

Balance restored.

I stayed awake most of the flight and watched about ninety percent of F1. Good movie. Finished it on the way back.

Arrival

At immigration, the same couple waved me into the resident line so I wouldn’t have to wait.

At this point, I was basically traveling with family.

They disappeared to their rental car. I met my driver. We drove off.

First impressions were solid. Calm airport. Friendly people. No chaos.

So far, Trinidad was doing its part.

The Hotel

Hyatt Regency Trinidad
Rating: 3.7 out of 5

Not bad. Not special.

Check-in was easy. Staff was friendly. Gym was good. Spa was legit.

The food, however, was aggressively expensive. One salad with shrimp was pushing thirty dollars, which caught me off guard. The billing was also confusing, with fees baked in before tip.

Breakfast was fine. Nothing I’ll remember in a year.

The biggest issue was location. I like to walk cities. Wander. Explore. This hotel wasn’t built for that. Outside the property, there wasn’t much calling my name.

The pool area, though, was alive. Most people were there to party. Carnival energy was in full effect.

That was not my ministry on this trip.

At dinner one night, staring at the menu, I ordered confidently, still riding the high of finally eating something other than a cookie.

How I Actually Spent My Days

This was not a “do everything” trip.

My days looked like this:

  • Wake up
  • Gym
  • Breakfast and a cappuccino
  • Work
  • Lunch
  • More work and creative time
  • Light exploring
  • Pool time with my laptop
  • Dinner
  • A little TV
  • Sleep

One day included a massage at the spa. Worth it.

It was a routine.

And that was the point.

The Part Where I Skipped Everything

The couple from the plane followed up. They texted. Called. Invited me out. Their nieces and nephews were in town.

I declined.

Not because I didn’t appreciate it.
Because I wasn’t in the mood.

I ran into them one morning at breakfast and could tell they were a little disappointed. I explained I had work to do.

Which was true.

Capacity is real. Travel doesn’t erase that.

The People

This was the highlight.

Kind. Open. Generous. Proud.

From the plane to the hotel, people were warm without being intrusive. Helpful without expecting anything back.

That stays with you.

The Verdict

The weather was perfect. A break from Miami’s cold stretch.

Would I go back?

Yes.
But:

  • With friends
  • For a specific event
  • Or in a different headspace

I’m glad I went.
I’m glad I rested.
I’m glad I added a new country.

That counts.

Quiet Takeaway

The best part of the trip was being in a position to reward myself with a little rest, relaxation, and an opportunity for new experiences.

Breaking routine matters.

Nothing big happened in Trinidad.
And that turned out to be the point.

What Came After

After I got home, I reached out to the couple from the flight.

I thanked them for their hospitality and explained a little more about where I was personally. They understood immediately. That warmth didn’t disappear once the plane landed.

I may have gone to Trinidad alone.
I may have skipped the parties.

But I might have left with new friends.

That alone made the trip worth it.

What’s Next

February is open.

Nicaragua or El Salvador.

We’ll see.

Quiet miles continue.