How A Baseball Cap Helped Me Virtually Eliminate Travel Regrets

“Twenty years from now you will be more disappointed by the things you didn’t do than by the things you did do. So throw off the bowlines! Sail away from safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover!”

This H. Jackson Brown, Jr., quote is a great motivator, an excellent reminder to seize the day. Carpe diem! Following the advice in the quote is also a way to help foil those occasional but inevitable travel regrets — those coulda, shoulda, wouldas. In my case, it was something more tangible than a quote that helped me virtually eliminate travel regrets. It was a baseball cap.

In 2007, our group was enjoying its annual trip to Jamaica for the Ocho Rios Jazz Festival. While shopping for souvenirs, my eyes landed upon a baseball cap with the colors of the Jamaican flag. There’s just something about the Jamaican flag that goes right to my soul. Jamaica is the only country whose flag contains neither red, white, nor blue. (In 2017, Mauritania adopted a new flag that has red, leaving Jamaica as the sole entry in the category.) Seeing the way the flag was emblazoned on the cap unrelentingly grabbed my attention.

Why Didn’t I Buy That Cap?

It was a very cool cap; black, with the flag somewhat compressed and placed right of center, running along the face and bill of the cap. The word “JAMAICA” was outlined in yellow. I fell in love with that cap. But I didn’t buy it.

I am not exactly sure why I didn’t buy it right then, but I do remember thinking, “It will still be here next year. I’ll buy it then.” As I walked out of the store, without the cap, the regrets began to make their presence felt. First, there was the uncertainty of coming back next year, even though I had made the previous five trips with our group. If I did come back the next year, would the store still have the cap?

The remorse about not buying the cap became all too real the moment our plane lifted off the runway as we flew back to the United States. I now had to live with that choice. But I was very lucky. I got a chance to erase that mistake. We were fortunate to be able to return to Jamaica the following year. I found the same store and it still had the same style cap. I immediately bought it.

Lessons From That Baseball Cap

True, a baseball cap is a small item in the scheme of things. But that cap did teach me a very valuable lesson: If there is something I want to do while traveling and it is within my means to do it, I should do it. You never know what the future holds. Will your schedule and/or budget allow you to return? Will your travel style change? Will travel requirements change? Will the place/excursion/item still be there in the future? How is your health? Any number of things can happen.

I have put this lesson into practice several times since that Jamaica trip. During one of my visits to Ensenada, Mexico, I happened to pass by a taco vendor who had, among many other offerings, manta ray tacos. Not wanting to pass up this opportunity (and not knowing if I’d be back in Ensenada), I purchased one. It tasted like chicken… that had been marinated in seawater. I’m not sure I’d buy manta ray tacos again, but I am definitely glad I tried it when I had the chance. Why? Because in three trips to Ensenada since then, I did not see that vendor or manta ray tacos being sold anywhere else.

Another example of applying this lesson is when we went on safari in Kenya and Tanzania. To me, Zanzibar was such an exotic-sounding location. When I was a kid, I thought Zanzibar was a mythical place that existed only in fanciful storybooks. As an adult, I learned that Zanzibar is in fact a real place, joining Tanganyika in 1964 to form the United Republic of Tanzania.

When I found out our safari would end just a hop, skip, and jump away from Zanzibar, I booked a two-day side trip to the island. We got to visit a spice plantation, see Freddie Mercury’s birthplace, and experience the singular dish that is Zanzibar pizza. I knew that if I was that close to Zanzibar and didn’t go, it would haunt me probably for the rest of my life.

Sometimes avoiding travel regrets may involve going a bit over budget. This happened recently during a trip to Sedona, Arizona. My wife and I saw an ad for sunrise balloon flights in the visitors guide magazine in our hotel room. I had never taken a hot air balloon ride before. The weather was warm and our schedule was clear until the afternoon, so we signed up. Once we got up in the air, we saw for ourselves why Sedona is such a popular place for hot air balloon flights. I am extremely glad we took advantage of the opportunity, even though it was outside what I had budgeted for this trip.

As much as participating in an activity is the main part of the lesson, so is intentionally not taking part in one. Here’s what I mean: On a circle island tour of St. Martin and Sint Maarten, our bus pulled up at one of the designated stops. I do not remember which one because I chose not to get off the bus. Instead, I stayed aboard and talked to the driver. Because all of the other passengers were out exploring, we shared a long, uninterrupted conversation.

I may have missed the point of interest we were visiting, but what I gained from this experience was a story about life on the island from the point of view of someone who lives there; a point of view that you will most likely never read about in any publication, print or digital. I can find photos of the area I missed in books or on the internet. But getting the driver’s perspective was priceless; well worth missing out on a few of the sights.

I’m Still Learning The Lesson

Even after learning and applying the lesson many times since that Jamaica visit, I recently neglected to follow my own advice and returned home with a big regret; hence the ‘virtually’ part in the title. As I walked up the stairs to get a closer photo of the Chimes Tower in Catalina Island, two women standing out on their balcony saw me. I asked them about vantage points for photographing the tower. A conversation ensued. They told me to take the walkway I was standing on, go across to the next road, and follow it up the hill. Taking their advice, I found the road, got right up close to the tower, and saw views of Avalon from a new vantage point, getting some nice photos in the process. They also suggested visiting a museum I didn’t even know existed and recommended a restaurant I should try that I’ve passed probably a dozen or more times.

Sounds great, right? How can there be any regret after such a nice encounter? Because I should’ve exchanged contact info with them, but didn’t. I really wanted to talk more with them about the changes that have taken place on the island over the last few years. Get their perspective as residents who have seen those changes first hand. Get their ideas on what to do that may not be in the guidebooks. Perhaps visit them the next time I go back to Catalina.

Though I have a lot less of them now, I admit, I’m still working on eliminating travel regrets as much as possible. As travel writer Helen Suk said, “To die is an inevitable reality for all of us, but an existence of unrealized potential, fear of failure and regret is not.” It takes a little determination, but I try my best to not put myself in a position of missing out — especially if the missing out comes about because I had the chance to do something and did not do it. This is something I am reminded of every time I put on that baseball cap.

You cannot change the past. You may not be able to recreate that trip. But you can take H. Jackson Brown, Jr.’s advice: Don’t end up being disappointed by the things you didn’t do.