5 Lessons I’ve Learned from Travel Mistakes I’ve Made

This post was last updated on 2024 April 21

I’ve learned a lot in my 10+ years of travel: about myself, about the world, about how to travel.

Lord knows I’ve made all sorts of travel mistakes – and as long as I keep traveling, I’ll keep making mistakes. But I try to learn from them and make them less and less over time, becoming a better traveler in the process – which ultimately results in better travel experiences.

Here are 5 important lessons I’ve learned while traveling:

1. Travel solo, or with people whose travel style meshes with yours

I took my first big trip when I was in 8th grade: a family vacation to Disney World, something I’d been dreaming of my entire childhood. In typical Lindsay fashion, I planned the entire week out in excruciating detail. My family put up with my hyper-planning as I corralled them up and out of the hotel at some ungodly hour each morning so we could beat the crowds and grab fast passes for the popular rides. We went to all the parks according to my schedule, and hit all the rides that I wanted to go on. I did every single thing I wanted to do at Disney World – it really was my perfect trip.

Four years later, just after I graduated high school, we took another family vacation – this time to Mexico, where we stayed at an all-inclusive resort just south of Cancun. My parents and sisters were in their version of heaven, content to lay on the beach all day, every day for a week; I quickly grew restless and orchestrated a day trip to Chichen Itza which was rushed and ill-enjoyed.

These two big family trips highlighted one very important fact: that I am a selfish traveler. I make no apologies for this – I believe that if you are going to invest a considerable sum of time and money into what’s likely a once-in-a-lifetime experience, you want to do it right – you want to do it your way. It’s unfair to make those you’re traveling with compromise too much; better to travel solo or in the company of those who have a similar travel style.

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Riviera Maya, Mexico

2. Don’t forget to eat and drink enough

This is not even remotely a problem for me in my day-to-day life, but when I travel I find that I tend to eat and drink less than I normally do. I get distracted by new (shiny!) things and places and would rather stay engrossed in that excitement than take the time to nourish myself. Oh it’ll be fine, I’ll just have a big meal or big pitcher of water at the end of the day, I rationalize during the day. This thought process has backfired on more than one occasion:

  • The time I hiked all day in Zion Canyon with just one small water bottle and got sick from dehydration. The residual sickness stayed with me for the rest of this Southwest US roadtrip and I wasn’t able to fully enjoy it because I didn’t feel well.
  • The time I hardly ate anything in India and fainted in the middle of town. Indian food was really hard for me to stomach, so I simply stopped eating it. After a few hours of walking in the heat, it finally caught up with me and I passed out in front of the Omelet Man in Jodhpur.

As much as I’d like to think I’m Superwoman and can power through my days with minimal sustenance, this is both untrue and foolish. It’s important to take care of yourself while traveling so that you’re able to enjoy your time and not have your plans ruined if you get sick.

travel mistakes
Zion National Park

3. Pack backups of your most important items

Far be it for me, the girl who always travels with at least 3 bags, to give advice on how to pack for a trip. Speaking from recent experience though, I do have a few thoughtful questions to pose for anyone gearing up for a trip:

  1. What are the things you absolutely CANNOT travel without?
  2. How easy would it be to obtain a replacement for these things while on the road?

Say you’re on a multi-week trek through Patagonia. If you’re asthmatic, what happens if you have trouble breathing on the trail and your inhaler malfunctions? If you’re a professional photographer or overzealous amateur, what would you do if your one camera broke just before reaching Torres del Paine?

You’d probably freak the heck out, that’s what. So back that ish up! Bring an extra inhaler; bring a backup camera. Whether you’re in a remote area or simply in a country where it’s not so easy to obtain a particular medicine or piece of technology, it’s worth packing a little extra for the insurance and peace of mind of having backups for your most important items.

solo female travel blog
Andaman Sea, Thailand

4. Travel slowly and take the time to truly experience and get to know a place

I’ve long been a champion of the Quality Over Quantity mantra, but it took several rushed trips for me to finally apply it to my travels. Yes, I’ve had a few 2-week marathon vacations where I foolishly attempted the following:

  • A roadtrip covering the coast, the major cities, and no less than 4 inland national parks from San Francisco to Seattle. About half of that time was spent in the cities, and the other half driving 1000+ miles and exploring some nature along the way. Lauren still chides me for making her drive 12 hours in one day up the NorCal coast because I was over-ambitious in our route planning.
  • Traveling all over Spain, hitting 4 major cities that weren’t even remotely close to each other. You know you’re over-extending yourself when you have to fly between two cities in the same (relatively small) country in order to cut down on travel time.

In earlier years, I was just so excited to be traveling that I wanted to go EVERYWHERE and do ALL OF THE THINGS. I still do – but over time, I’ve learned to curb my travel bingeing and accept that IT’S OKAY that I won’t see everything on one trip. I’ve realized that it’s more fulfilling to spend more time experiencing fewer places. Better to get to know a place more thoroughly and intimately, rather than just scratch the surface of a few different places and spend too much of your already-limited time getting from A to B to C.

Not only will your travel experiences be better for taking it slow, but also your travel memories. The west coast of the US is a beautiful blur to me today, but the 5 days I spent on Lady Elliot Island 8 years ago are so clear that I can actually go back in my mind and relive the experience of snorkellng in a reef maze and turning my head right to see nothing but a big ol’ manta ray swimming past me.

The fact is, we retain more when we give ourselves more time to experience and process something, rather than cramming it into a shorter period of time. I want to look back on my adventures 5, 10, 50 years from now and think something a little deeper than “Oh, that was a good time”.

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Redwood Forest, California

5. Allow more time than you think you’ll need

Of all the travel mistakes I’ve made, this is the one that is the most difficult for me to stop making. As a person who is unapologetically 3-5 minutes late to everything, I know by now that I should allow myself more time to get somewhere – I simply choose not to, because I would rather be a few minutes late than early. I get immense satisfaction out of allotting *just enough time* for something, and minimizing time wasted (in places I’m not enthralled with, in airports, waiting for people to arrive, etc).

The problem is when *just enough time* turns into *not enough time*, which can be a big problem when you’re traveling for a certain number of days. Not having enough time has been a problem on more than one travel occasion for me:

  • Not budgeting enough time for places I ended up LOVING, such as Barcelona and Waimanu Valley. Had I traveled more slowly (see #4 above), I’d have had the flexibility to spend a bit more time in a place that I ended up loving before having to hop on a plane home.
  • Traveling with a soon-to-expire passport. Mine would be valid for *exactly* 6 more months as I was due to enter my last Asian country in 2013 (most Southeast Asian countries require at least 6 months validity upon entry). I hadn’t expected my plans to change so drastically that I’d want to enter a new country after that date, so I was “stuck” in Thailand for my last couple weeks in Asia. I should have renewed my passport before traveling to Asia so that I’d have had more flexibility in my travels.
  • Not having enough time between flights to make a connection, e.g. on my recent trip to Colombia. Technically we had more than enough time to make our connection in Bogota, assuming our first flight took off from Cartagena as scheduled. But if it was delayed or cancelled (as it was), we’d miss the ONE flight from Bogota to New York that night. We should have booked one of the earlier flights to Bogota, even if it meant having more time than desired waiting at the Bogota airport before our next flight.

To avoid not having enough time for something, it’s better to schedule more time to cover fewer places or activities while traveling.