I developed a passion for travel as a teenager, but didn’t get to fully realize that passion until I was in my thirties. However, I did enjoy many weekend camping trips and day trips to beaches and theme parks. Having a child young meant that my priorities shifted away from my dreams of traveling the world, but I did take one week away when he was nearly two years old.

I was a 21 year old college student and mother who needed a break from reality, so I took a road trip with two friends (a guy I went to school with and his girlfriend) and drove to Naples, Florida for spring break. Not your typical spring break stop, Naples is a wealthy coastal town with a more mature population. The parking lots resembled car shows and the homes were huge with beautifully manicured lawns. Not surprisingly, we couldn’t afford any of the hotels along the beach so we chose a motel on the highway that we dubbed the “roach motel” for good reason. Aside from the pesky roommates we discovered, we enjoyed our time there. We spent little time at the motel but while we were there we hung out on the lawn at some picnic tables. It happened to be bike week and most of the other rooms were occupied by bikers and they preferred to spend time outdoors too, so we all hung out together exchanging stories and sharing a drink or two.

Most days were spent on private beaches that we wandered onto without flinching. This is where I encountered David Letterman, without realizing it was him. I was taking a walk along the beach, attempting to find some time to myself. The beach was lined with regal beach houses and my walk was essentially taking me across their “backyards”. Sitting outside of one of these homes was a man smoking a cigar. He smiled at me and said hello and I reciprocated then continued my walk. I noted how much he looked like Letterman but it didn’t occur to me that it was him. We exchanged greetings again on my way back and I didn’t think of it again until we were watching the Late Night with David Letterman a few days later. He said he just returned from a vacation in Naples, Florida and I realized that it was possibly him on the beach. I was still unsure because I didn’t think that Letterman smoked cigars. It turns out that he did, and I most likely greeted David Letterman on the beach twice, without ever acknowledging who he was. I’m sure he appreciated that though, especially since I was probably trespassing.

Meeting people and having new experiences is what appeals to me the most about traveling, and what sustains my passion for travel. Of course I love to stay in a beautiful resort, but that is not a requirement for me. I want to see where the locals hang out and shop outside of the tourist zones. Some of the best meals come from greasy spoon diners that aren’t listed in the tourist brochures, and beauty can be found anywhere.

2 Replies to “That Time I Sort-of Met Letterman and Developed a Passion for Travel”

  1. Sounds like he is a really nice person, it’s perhaps for the best that you didn’t know he was the real thing 🙂

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