Why the Best Travel Photos Aren’t on Your Itinerary

You’ve booked the trip, packed your gear, and mapped out every perfect shot—but what if the best photos are the ones you never planned for? The magic of a photo trip isn’t just in the locations; it’s in the unexpected moments, the wrong turns, and the stories that unfold when you stop chasing perfection. Before you overstuff your itinerary and your camera bag, here’s what you should do (and avoid) to make your next photo trip unforgettable.

Over the last few years, I’ve hit the road more than I ever dreamed possible, embarking on numerous adventurous photo trips. In 2023, I explored the breathtaking White Sands National Park, traveled through several vibrant Midwestern states, and took a trip to bustling Washington, DC. Last year was an epic 3,000-mile journey along the iconic Route 66. As for 2025, my travel plans are still in the works, but I can't wait to see what adventures await! With all these trips, I planned and planned—and planned a little too much. What I learned is up next!

Embrace the Unexpected

A once-in-a-lifetime trip or photographic workshop requires significant planning. I plan every trip, but one lesson that Route 66 taught me is that overplanning stifles creativity. I captured screenshots of locations and created an itinerary for each day to ensure I wouldn’t miss anything. I arrived in Los Angeles and hit the open road the next day at 4:00 a.m. I focused on all the stops on my first full day. At the end of the first day, I realized one thing: I had missed a few stops! I thought to myself, Why? It was an easy answer. I was too focused on getting somewhere fast and not missing things, and in return, I did just that—I missed a few stops. The next day, I threw the itinerary out the window—figuratively! I focused on one thing: hitting the open road.

It was exhilarating; I had nowhere to be in a hurry. Once I started that, I didn’t worry about the time—I was feeling alive and creative! I stopped worrying about all those screenshots I saved and all the books I bought and started enjoying the adventure at hand. With that came the creativity and the adventure that Route 66 is all about! I was beginning to see images that were my vision and not others’. So what I am trying to say is that overplanning kills creativity! Planning is essential, but overplanning is not.

I also found the best photographs were taken outside of the itinerary. When people go left, I tend to go right. You never know what you're going to find off the beaten path, and Route 66 reminded me of that. This has happened on other trips, including my trip to Glacier National Park, where I went left when everyone else went right. I ended up with a great image because I didn’t follow the pack. You will start to find locations and subject matter that many have overlooked because they follow that itinerary they saw blasted all over the internet. They create images that five million others have taken!

Pack Light, Think Smart

I overpacked for Route 66 on gear, which is not a great idea. I was never far from the vehicle, but I had things I probably didn’t need. In the end, 99 percent of my images were taken with the Nikon Z 24-70mm f/4 and a few with the Nikon Z 70-200mm f/2.8. As a wise man once said, less is more, and it's true. Too much gear can make you overthink and switch to different lenses when that is not needed. We do this because we feel we must validate all the gear we brought!

The only thing I did right in terms of gear was buying extra batteries, just in case I couldn’t charge them daily. Occasionally, that happened. However, one thing I didn’t think about was rain gear for the camera. I spent a day and a half in solid, heavy rain, bringing me to my next point—the must-haves!

My most overlooked gear was rain protection from Think Tank! I left it behind and needed it—the good one. I had a cheap backup about as thick as a plastic bag from Op/Tech. It worked and helped me limp along! I guarantee you won’t miss packing the essentials for your camera gear. It’s the non-photo gear that often gets overlooked. Extra clothes, pen and paper, chargers—all the little things. I forgot a sweatshirt and regretted it! I finally found a store where I could buy a cheap zip-up jacket, saving the day at a price.

Chase Moments, Not Instagram Shots

With a lot of research, you start to saturate your brain with others' images and subconsciously recreate them. Researching locations is not harmful; just be aware when you're shooting that you are not merely recreating images you have seen before. That said, taking the “insurance shots” is okay. You can put your own twist on these well-known locations. These photos will at least let you leave with a few great images!

Bad weather? Don’t fret—some of the best images can be made in the worst weather! If you're caught in a rainstorm in a location that rarely sees rain, you now have images that very few others have! The light can also be best during or after storms, allowing you to create stunning photos. If the rain shows up or clouds roll in, embrace it as a challenge and push yourself to create images.

People Over Places

One of the best examples of this was breakfast at the Rock Cafe in Stroud, Oklahoma. After my long visit and big breakfast, I didn’t want to leave! I was attending the local conversation by invitation. They wanted to know where I was from and what I was doing. After I told them I was traveling Route 66, they were not surprised because Route 66 was right out the front door. I learned about all these unique little stops I didn’t know about. They told me everything I needed to know, but the internet could not tell me because, well, it's the internet. Remember, talk to the locals. They know all the gossip and have likely lived there all their lives. They are a wealth of knowledge and have insights most do not!

Speaking of locals, remember to respect property and culture. You're just a soul passing through, so don’t ruin it for the next person because a few bad passersby can ruin it for the rest. Sometimes, outsiders are banned from some of the most incredible locations due to others not respecting them. You can see this on Route 66, as many places have No Trespassing signs because others can’t respect another’s property. When you show respect, it sometimes pays dividends. I was at the old 76 gas station that was being restored into a restaurant near Valentine, Arizona. I respected the property and didn’t want to go onto it. A truck pulled up, and I thought, "Oh no, here it comes." I was expecting the usual: "How about you get on your way?" conversation. What it led to was: "Hey! Do you want me to open the gate to show you around?"

I also had a great conversation with a great guy named Rubin at the Hackberry General Store. He owned and lived in the old Valentine Station down the road, and he was polite enough to tell me to stop by as I passed and take all the photos I wanted. The best part is that I have talked to Rubin via social media over the last year! You might meet a new friend or two on your adventure!

Know When to Ditch 

Logistics play a huge part in any trip, but know when to ditch them and expect the unexpected! I was in Missouri, had a long 13-hour day on the road, and was ready to go to bed for the evening. Two problems. First, the RV park I was staying at knew I was coming, as I had checked in several hours earlier and told them I would be there late. They were okay with that, yet they rented my space out. Second, the owner was out of town, and the groundskeeper who was supposed to check me in was nowhere to be found. I hope he has been found to this day! Well, I just rolled on down the road and found a hotel to stay in. Know when to ditch the plan and don’t let it get in your way.

You must also know when to ditch the camera and enjoy the moment. I can get hyper-focused looking for images and forget why I was going—to enjoy a fantastic trip. Several times, I just left the gear in the truck, hit the road, and, with the windows down, cranked up the volume on my Route 66 playlist on Spotify and enjoyed the adventure!

Let the Trip Shape Itself

Detours are always a roadblock you should expect to encounter, whether the detour is your choice or not—but mostly not your choice! I discovered a few of these while traveling Route 66, like part of the route near Amboy, California. Unfortunately, I had to travel by interstate for a while. It was not what I wanted to do, but it was a necessity. I did find a few stops that were not planned, but they were great overall. Failures can also creep up! I planned a few stops that were a waste of time, and that will happen occasionally. Remember to take it as a learning moment and go along your way!

Capture the emotion, not just the location! Listen to what your gut is saying, and remember to look at your locations from the perspective that you are there to tell a story, evoke an emotion, or bring back a forgotten thought from an individual. You're not there just to document a location, create a record of the area, or take a snapshot.

In the End

Whether it's a once-in-a-lifetime trip, a photo workshop, or an everyday location, there is always a planning aspect when you pick up your camera. While overplanning can seriously hinder your creativity, it can also help you create some of the most epic adventures of your lifetime. In all, get out of your comfort zone and that overplanning mindset, and rewire your thinking to include the fact that trials and tribulations are a part of the photographic process and the adventure.

How do you balance capturing moments with actually enjoying the experience of travel? I would love to see your answers in the comments below!