5 Travel Mistakes I've Made (And What I'd Do Differently)
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I've traveled to some incredible places over the years, but not every adventure has gone according to plan. I've missed places I desperately wanted to see, underestimated the weather, packed way too much into a single day, and even lost an entire collection of travel photographs.
And while I'd love to say I've learned to avoid every possible travel mistake, I think we both know that's probably not going to happen. Travel comes with unexpected challenges. Sometimes those mishaps turn into your favorite stories, while other times they leave you kicking yourself for months. When you have limited vacation days, those mistakes can be especially frustrating. Missing something you've traveled halfway around the world to experience isn't exactly how you want to spend your PTO.
Over the years, I've learned quite a bit from things going wrong, especially during my earlier trips when I was still figuring out how to plan my own adventures.
Here are five travel mistakes I've made, what happened, what I learned, and what I'd do differently today. Hopefully, you can learn from my experiences and avoid making a few of these mistakes yourself!
At a Glance
Mistake #1: Not Properly Researching the Places I Wanted to Visit
Location: Cinque Terre, Italy
During the summer of 2019, I traveled to Italy on a group trip with EF Ultimate Break. While making our way from Milan to Florence, we stopped in Cinque Terre for the day.
If you're familiar with Cinque Terre, you've probably seen the famous photographs of colorful buildings stacked along the cliffs overlooking the Mediterranean Sea. You know the ones. They seem to appear everywhere, from Instagram to travel magazines and even those old preset computer backgrounds.
Well, I wanted that photograph.
Here is where you go to get “the photo.”
Here is where I was.
I knew what the photograph looked like, but apparently I hadn't thought about the fact that I would need to find the specific viewpoint from which to take it.
After exploring Manarola, we hopped on another train and made our way to Monterosso, where we spent some time relaxing on the beach. While sitting there, I turned to my travel companions and asked when we would visit the place where everyone takes that famous Cinque Terre photograph. They looked at me and said, "We were just there!" Are you kidding me?
I'd managed to visit the exact village I wanted to photograph without actually making it to the viewpoint I'd been looking forward to the entire trip. Definitely a facepalm moment.
What I'd Do Differently
One of my favorite things about traveling is discovering places I didn't originally plan to visit. I don't want every minute of a trip scheduled, and I certainly don't want to spend an entire vacation following a checklist. However, I've learned that there's a difference between leaving room for spontaneity and failing to research something I really want to see.
These days, if there's a particular viewpoint, attraction, or photography location I absolutely don't want to miss, I research it before leaving. I recommend saving important locations directly to Google Maps, looking at photographs taken by other travelers, and figuring out exactly how to reach them.
If you're planning to photograph a specific location, it's also worth researching what time of day provides the best lighting. A little extra preparation can make a huge difference, especially when you're only spending a few hours somewhere.
And if you find yourself in Manarola, make sure you walk far enough along the coastal paths to find those incredible views!
Mistake #2: Not Checking the Weather
Location: Sequoia National Park, California
In 2020, like most people, I found myself spending considerably more time exploring places closer to home. I traveled to California twice that year.
During my first visit in late summer, I made my way to Sequoia National Park and absolutely fell in love with its giant sequoia trees. If you've never seen them in person, it's difficult to explain just how massive they are. Naturally, I wanted to go back. A couple of months later, I returned to California for a West Coast road trip and made sure to squeeze in another visit to Sequoia National Park. Unfortunately, we never made it to the trees.
Okay, that sounds a little more dramatic than it actually was. Coming from Los Angeles, I hadn't even thought about checking whether it might have snowed in the mountains. When we arrived at the park entrance, we were informed that it had snowed the night before and that tire chains were required to reach the area we wanted to visit. Not a problem, right?
Apparently, we could rent chains from a nearby town. Now, I'm from the Northeast. I'm certainly no stranger to snow, but I'd never installed tire chains before. That was about to become very obvious. We spent the next two hours renting chains, trying to learn how to install them from a video playing on the wall, and attempting to make our way through the park. We eventually reached a scenic overlook where several other cars were also struggling to install their chains.
We tried. And failed.
After making a little more progress along the winding mountain road, we finally accepted that continuing wasn't worth the risk. We weren't properly prepared for the conditions, and getting ourselves into a dangerous situation just to see the trees wasn't a particularly good idea. So we turned around. Two hours of dealing with tire chains, and I still didn't get to see the giant sequoias. At least I had a pretty funny side story to bring home. There was a UPS truck up there making a delivery! I couldn’t believe that it made it up there. That's dedication.
What I'd Do Differently
This experience taught me that checking the weather for your destination isn't always enough. You also need to understand the conditions along the route you're taking. The weather in Los Angeles was nothing like the weather we encountered in the mountains. Elevation, seasonal changes, and unexpected storms can dramatically affect your plans, particularly when you're visiting national parks or driving through mountainous areas. Before heading out, I now recommend checking the weather forecast, road conditions, seasonal closures, and any special vehicle requirements.
If you're visiting Sequoia National Park, check the National Park Service's current road and driving information before your trip. Snow and ice can affect access well outside the middle of winter. It's also important to understand your rental car agreement. Some rental companies don't allow tire chains, even when road conditions require them.
And most importantly, know when to change your plans. As disappointing as it was to miss the trees, continuing up an unfamiliar mountain road in unsafe conditions would have been a much bigger mistake. Sometimes, the best decision you can make while traveling is knowing when to turn around.
Mistake #3: Planning Way Too Much Into One Day
Location: Iceland's South Coast
Iceland is one of my favorite countries, and this particular trip is probably one of the reasons I've learned to be a little more realistic when planning my itineraries. During my first visit to Iceland, I traveled with EF Ultimate Break and fell in love with the country. Later that same year, I returned with two friends as the final stop of my first independently planned backpacking trip through England, Ireland, and Iceland. I was so excited to show my friends all the incredible places I'd visited during my first trip. I'd been talking about Iceland nonstop, and now I finally had the opportunity to share some of my favorite locations with them. Naturally, I wanted to show them everything.
We planned a weekend road trip along Iceland's South Coast, filling our itinerary with geysers, enormous waterfalls, glaciers, and as many other attractions as we could possibly squeeze into our limited time. We spent the day exploring, taking photographs, and stopping at a local grocery store to stock up on snacks before continuing toward the glaciers. There was just one thing I hadn't properly accounted for. It was late October. And in Iceland, daylight becomes increasingly limited as winter approaches. We'd spent so much time enjoying the attractions earlier in the day that we ended up driving toward our next destination in complete darkness. By the time we arrived at the glacier, we couldn't see much of anything.
Looking back, that probably should have been our sign to turn around. But I was determined. We'd already driven that far, and I wasn't particularly interested in giving up on the rest of our plans. So, naturally, we continued.
Our next stop was Jökulsárlón Glacier Lagoon, approximately another 45 minutes up the road. And that decision led to one of the most unexpected experiences of the entire trip. Unfortunately, it also led directly to my next travel mistake. But we'll get to that in a minute.
If you're planning your own Iceland adventure, check out my three-day Golden Circle and South Coast road trip itinerary for a more realistic way to organize your time.
What I'd Do Differently
I've always been someone who wants to see and do as much as possible when I travel. When you're working with limited vacation time, it's tempting to squeeze every attraction you can into your itinerary. But there's a big difference between making the most of your time and creating an itinerary that's practically impossible to follow. These days, I try to plan my days around the attractions I absolutely don't want to miss. Everything else is a bonus.
I also recommend checking sunrise and sunset times before building your daily schedule, particularly when you're traveling somewhere like Iceland, where daylight hours change dramatically throughout the year. Another thing I've learned is to account for the time you'll inevitably spend doing things that aren't part of your original plans. You might need to stop for gas, grab something to eat, wait out bad weather, or spend an extra hour photographing a waterfall because it's even more incredible than you expected. And sometimes you'll discover something completely unexpected along the way. Leave room for those experiences.
If you're running behind, don't be afraid to remove something from your itinerary. I'd rather thoroughly enjoy five incredible locations than rush through ten simply because I put them on a list. And while our unexpected nighttime adventure in Iceland turned into an incredible memory, I wouldn't recommend continuing through unfamiliar landscapes in darkness simply to check off another attraction. Sometimes you really do need to accept that you can't see everything in one trip.
Mistake #4: Not Backing Up My Travel Photographs
Location: Jökulsárlón Glacier Lagoon, Iceland
Remember that unexpected Iceland adventure I mentioned? Well, here's how it continued.
After arriving at the glacier and realizing it was too dark to see anything, my friends and I decided to continue toward Jökulsárlón Glacier Lagoon. If you're unfamiliar with Jökulsárlón, it's an enormous glacier lagoon filled with icebergs that break away from Breiðamerkurjökull, an outlet glacier of Vatnajökull. The icebergs float through the lagoon before eventually making their way toward the ocean. Depending on the conditions, the lagoon can be filled with an incredible number of enormous pieces of ice.
Unfortunately, we arrived in complete darkness. But as we drove toward the lagoon, the headlights of our car began illuminating enormous pieces of ice floating in the water. I was so excited. We got out of the car, made our way toward the lagoon, and stood listening to the sounds of ice cracking in the darkness. It was unlike anything I'd ever experienced.
Of course, being the photographer that I am, I immediately started thinking about how I could capture it. I ran back to the car, grabbed my camera, and attempted a long-exposure photograph. Without a tripod available, I propped my camera up on a nearby sign and hoped for the best. And that's when we realized what we were actually standing in front of. The long exposure revealed an enormous collection of icebergs floating throughout the lagoon. It was incredible! We were absolutely ecstatic. We spent the next half hour taking timed, long-exposure photographs of the three of us standing in front of the ice. It was one of the most unexpected and memorable moments of the entire trip. I couldn't wait to get home and look through the photographs. And then I made one of the most frustrating mistakes I've ever made as a photographer.
We were at the end of an almost two-week trip, and I'd gotten a little too relaxed about backing up my memory cards. I kept telling myself I'd take care of everything once I got home. Well, I didn't. A couple of weeks later, I formatted my memory card. And just like that, all those photographs were gone. Every single one of those incredibly long-exposure photographs we'd taken at Jökulsárlón. I still get frustrated thinking about it. If there's one thing I wish I could go back and change about that trip, it's making sure I backed up those photographs.
One important note: As incredible as that experience was, I wouldn't recommend approaching an unfamiliar glacier lagoon's shoreline in complete darkness. Ice, unstable ground, and deep water can create serious hazards, and photographs are never worth taking unnecessary risks.
What I'd Do Differently
This mistake completely changed the way I think about protecting my travel photographs. You can revisit certain destinations, but you can't always recreate the same experiences. The lighting, the weather, the people you're traveling with, and those unexpected moments that make a trip memorable are often impossible to duplicate. That's why I recommend creating a backup routine before leaving for your trip.
If you're traveling with a camera, bring enough memory cards to avoid repeatedly formatting them while you're away. Whenever possible, back up your photographs to a portable external drive, your computer, or cloud storage. Ideally, have at least two separate copies of your photographs before deleting anything from your memory cards. And don't just assume your files have been copied successfully. Take a few minutes to open them and make sure everything transferred correctly.
I also recommend keeping backup copies in separate places when possible. That way, if your camera bag gets lost or stolen, you haven't necessarily lost every photograph from your trip. For me, travel photography is one of the most important parts of exploring the world. Coming home with photographs that remind me of my experiences is something I genuinely treasure. Losing an entire collection because I didn't take a few minutes to back it up is a mistake I don't intend to repeat.
Mistake #5: Not Stopping for Gas
Location: Ireland
This one might seem like a no-brainer. But where I live, there are four gas stations at the end of my street. All on the same corner. Seriously.
As you can probably imagine, I've developed a pretty bad habit of waiting until my gas tank is getting low before bothering to fill it up. That's not necessarily a great habit when you're road-tripping through somewhere a little more remote. During a trip to Ireland, a friend and I were driving from Galway toward the country's western coastline. Our destination was the Cliffs of Moher, one of Ireland's most famous natural attractions. We'd planned to visit Doolin first, take a ferry to see the cliffs from the water, and then head toward the visitor center to experience the more familiar views from above. It was going to be an incredible afternoon.
There was just one small problem. I had approximately a quarter tank of gas left. Rather than stopping to fill up, I figured we'd worry about it once we got a little closer to our destination. After all, how difficult could it be to find another gas station? Apparently, more difficult than I expected. We were driving along one of the narrow, hilly roads in the area when the car suddenly shut off as we were heading uphill. I let the car roll backward down the hill and tried again. No luck. We made several attempts, but the car simply wasn't cooperating. At the time, I suspected our low fuel level and the incline might have had something to do with it, although we never confirmed the exact cause. Regardless of what was happening mechanically, we were now dealing with an unexpected problem on a narrow road, and the sun was quickly approaching the horizon. By the time we figured out our next steps, we no longer had enough daylight to make it to the Cliffs of Moher.
So much for that plan. All because I'd decided to put off dealing with something as simple as stopping for gas. The good news? I eventually returned to Ireland and finally experienced the Cliffs of Moher on another trip. And yes, they're absolutely worth visiting.
What I'd Do Differently
One of the biggest lessons I've learned from road-tripping is that the seemingly insignificant parts of your itinerary can sometimes have the biggest impact. It's easy to spend hours researching attractions, restaurants, photography locations, and scenic drives while completely overlooking the time you'll need for everyday things. Getting gas, picking up groceries, stopping for food, and taking breaks might not be the most exciting parts of your travel plans, but they're still important.
When you're driving through unfamiliar areas, particularly remote regions or places where services are spread farther apart, I recommend filling up well before your tank gets low. Don't assume there will be another gas station just around the corner. And if your vehicle starts behaving unexpectedly, pull over somewhere safe and address the problem rather than repeatedly attempting to continue driving.
I would also build a little extra time into your itinerary for unexpected delays. When you're trying to reach an attraction before sunset or make it to a reservation on time, even a relatively minor inconvenience can throw off the rest of your day. And believe me, you'll be much happier spending that extra time enjoying your destination rather than worrying about whether your car is going to make it up the next hill.
Looking back at these experiences, I can laugh about most of them now. At the time, though, missing a place I desperately wanted to photograph, struggling with tire chains on a snowy mountain road, or accidentally deleting an entire collection of travel photographs definitely wasn't funny. Each of these mistakes taught me something about the way I travel today.
I've learned to do a little more research before visiting places I really want to see, check the weather and road conditions, leave room in my itinerary for the unexpected, and take much better care of my photographs. I've also learned that sometimes you need to accept that things won't work out exactly as you planned. And that's okay.
Some of my favorite travel memories have come from unexpected experiences that never would have happened if everything had gone according to plan. That doesn't mean I'm going to stop planning my trips or start intentionally making bad decisions. But I've learned to be a little more flexible, a little more prepared, and a lot more willing to change my plans when necessary. After all, the goal isn't to have a perfectly executed itinerary. It's to make the most of the time you have, experience incredible places, and come home with some unforgettable memories.
Preferably with all your photographs safely backed up.
What's the biggest mistake you've made while traveling? Did it end up becoming a good story?
Happy travels!
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