This year, I will make my fourth annual pilgrimage to Key West.

What is it that’s so special about this place?

It’s not the white sandy beaches of Florida’s Gulf Coast or the clear blue-green waters of the Caribbean. No, Key West is something unique.

My very first trip to the Keys was to celebrate my 50th birthday, a milestone we never really got to celebrate properly during COVID. When my wife asked if I wanted to do anything fun for my birthday, I told her I wanted to fly to Miami, rent a convertible, and drive all the way down to Key West.

So, in September of 2023, we flew to Miami. I rented a red convertible VW Bug, fired up a four-and-a-half-hour playlist, and we started our adventure.

We stopped to see the big lobster in Islamorada, and at the very first restaurant we visited, I simply told the server, “I’ll have whatever the fresh catch is, prepared however the chef recommends.”

Why Key West, though?

First, it was the music vibe. Think Buffett, Kenny Chesney, Zac Brown, and the like.

Second, I love the water. There were endless options for swimming, snorkeling, and sailing. And, of course, water means fresh seafood.

Third, it was my birthday, and I’ve never been one to turn down a good time. And Key West is a damn good time. There aren’t many vacations where you don’t even second-guess yourself for cracking a drink at 11 a.m.

Lastly, and this is the nerd in me, Key West is home to the Hemingway House. As an English major and a lover of cats, this place had everything and had long been on my bucket list.

Before we left, a good friend mentioned that he knew the third-generation owner of a cigar factory and reached out to let him know we were visiting. On our first day in the Keys, we headed downtown to the infamous Duval Street.

We stopped by one of the dozens of T-shirt shops to pick up something for the kids. Upon entering, the shop owner immediately struck up a conversation with us. He was definitely on island time. We stayed much longer than I anticipated because the conversation was just so genuine. However, I found myself continually glancing down at my watch, thinking, We need to go. I’ve got so much I want to do.

We finally broke free and made our way to Rodriguez Cigars, where we asked for Danny DiFabio, the owner. He came out and immediately gave me the warmest bro-hug, as if I’d known him forever. He mentioned there was a tour going on and insisted we stay as his guests.

We learned all about cigar manufacturing, and I even got to roll my own cigar. After the tour, we spent another hour or more just talking to Danny. We chatted about our families, our faith, and the ups and downs of running a business.

For the first time in a long time, I felt a weight lift off my shoulders. I witnessed time stand still, and honestly, I didn’t even care what time it was.

We hugged and said our goodbyes. After walking a block or so, I stopped, turned to my wife, and said, “I have got to learn to slow down.”

Why am I always looking for the next thing?

Why am I looking past people when talking to them at a networking event, just to plan who I want to talk to next?

For the remainder of our trip, I decided I didn’t want to schedule anything, except for our sunset sailing trip. I wanted to wake up, go for a run, and relax with my coffee until my wife woke up. Then, we’d grab breakfast and see where the day took us.

It was the most amazing week.

I told my wife that I wanted to come back here every year to remind myself of this feeling.

When I shared this story later with a dear friend, she said, “Oh honey, I’m so sorry it took you this long to learn the difference between going on a trip and going on vacation.”

The ongoing challenge now is figuring out how to make sure that Key West vibe lives beyond the island.

One simple thing I’ve started doing is eliminating the phrase “looking forward to” from my vocabulary. We should never look past what is happening right now. I’ve been trying to stay as present as possible in every situation, making sure the people I am with know that I am all in.

As Ernest Hemingway once wrote, “It is good to have an end to journey toward; but it is the journey that matters, in the end.”