More Dumb Travel Mistakes I Won't Repeat

Written By Krista Nannery

You guys really loved my 2024 version of The Dumbest Travel Mistakes I’ve Ever Made, so here’s my 2025 version! Enjoy. And hey, I love to share reader stories. If you’ve got an entertainingly dumb travel mistake, contact me! I might feature your story in a later installment.

Mistake #1: Not traveling after I graduated from college.

After I graduated from college, I was bored so I got a temp job at a travel agency in Florida entering data for -- surprise surprise! -- a chain of all-inclusive honeymoon resorts in the Caribbean. But apparently I entered the data a lot faster than anyone else in that role had ever entered the data. I entered the data so fast that no one believed that I had entered all the data or had entered it correctly. The company spent more time checking my work than I spent entering the data. For a 22-year-old new to the professional world and wanting to do her best, it was all very disconcerting. I should have just booked one of those whistle-stop tours of Europe instead!

If you know someone graduating from college right now and if you want to gift them a trip to Europe, I’m your girl. I have so many great trips to Europe – of all different lengths – for young people. Travel is an amazing graduation gift! Let’s talk.

Mandalay, Myanmar. I can recommend reading The Glass Palace by Amitav Ghosh.

Mistake #2: Being cheap with hotels in Myanmar and DIYing it.

Why oh why did I go to someplace like Myanmar and stay in 3 star hotels? This was a BIG mistake. When you are in an uncertain country, do yourself a favor…stay in a nice hotel. Everything will be much nicer and you’ll be so much more comfortable, I promise you. Places like Myanmar are not where you want to be winging it. (This was back in 2018, a relatively quiet and safe period. But still…an uncertain country where I should have been paying more attention.) I should have done a package tour or hired a travel agent to help me with this trip. The worst was my transfer back to the airport on my way home. The driver was acting so strange that I seriously wondered if I was being kidnapped.

Mistake #3: Thinking cruising is boring.

I really disliked my first ever ocean cruise. Not knowing any better, I booked an inside cabin for my mom and me direct with the cruise line over the phone. The call center actually hung up on me because I was asking so many questions. I should have used a travel agent to help me with this trip.

My next cruise was a multigen family cruise to Alaska with Holland America. My cousin booked everything with an agent who knew what they were doing and this time my mom and I had a prime location balcony cabin. We had a fantastic time. In port in Alaska one afternoon, I remember looking up into the trees at one point and there were thousands of bald eagles, waiting patiently for lunch. (Salmon, not me.)

A cruise can be the perfect multi-gen getaway. There’s truly something for everyone. If you need a cruise, I’m your girl. Let’s connect.

Mistake #4: Taking the ferry from Fort Lauderdale to the Bahamas.

This sounded like such a fun idea at the time. Plus, I’ve taken ferries in Greece. How bad could it be? Well, it was not great. Greek ferries are a machine. There are many of them and they compete with each other and they have different fare classes. Our ferry was packed and there was also something wrong with it — both ways. We limped into port on arrival and departure. I really cannot recommend taking the ferry from Port Everglades to the Bahamas. Please just fly.

Why ride a camel alone when you can ride with others?

Mistake #5: Thinking group tours are not for me.

I thought I was an independent traveler. I had been all over Europe in my early 20s. But then in 2000, I wanted to go to China. I kinda figured that China was not the sort of place I should go to alone. So I booked a group tour with Backroads and to this day, it remains one of the best trips I ever took in my entire life. Our guides, Paul and Jo, were fantastic. (In fact, Paul just celebrated his 400th trip with Backroads last year.)

Then, in 2010, before I left London the first time, I decided that I should go on a trip that “Pre-London Krista” probably would never have gone on. So…I went to Jordan and Syria. With Gecko, which is now part of Intrepid. (2010 Syria was a different time. All I did in Syria was eat pistachio ice cream, buy olive oil soap, and fend off offers for my iPhone.) My tour guide in Jordan was one of the best tour guides I have ever had in my entire life. And I am still friends online with many of the people I met on this trip.

So now…I’m a big fan of group tours. They can be a fab way to see a country. You cover a lot of ground and meet a lot of like-minded travelers. Don’t knock it til you try it, folks. I have so many group tours for clients in my storehouse. Budget, mid-range, and luxe. You name it, I’ve got it.

Mistake #6: Neglecting to check visa requirements.

Always, always read the instructions. When I applied for my Syrian visa, I overlooked the part that said that Americans must apply through the Syrian Embassy in Washington DC. As I note above, I was living in London at the time! Cue me having a panic attack a month before my trip departure date IN the actual Syrian Embassy in London, with the alarmingly handsome Consul General himself telling me he did not feel sorry for me given how poorly he had been treated by the US government when he lived in New York City.

Way to take it out on a nobody, dude.

So yeah, always read the visa instructions. (It all worked out in the end. Through the wonder of the internet in 2010, I learned that there was this ONE GUY named Hassan at the Syrian Embassy in Washington DC who processed visas for Americans. He was great.)

Mistake #7: Not securing my valuables.

A few years ago, I flew from Bangkok to Colombo, Sri Lanka. Before I checked out of my apartment hotel, I did one final sweep and realized that I had forgotten a dress in the dryer and I had also forgotten my portable speaker. I wrapped the dress around the rectangular speaker and threw everything into the top of my suitcase. Normally I lock my suitcase but for some reason…not this time.

Well guess what? I arrived in Colombo without my purple dress (that I had had custom made in Vietnam) and without my portable speaker. The speaker I could replace, but I loved that custom made dress!!

Most crimes are crimes of opportunity. Don’t be all proud of never locking your luggage. Lock your luggage!

Mistake #8: Accidentally booking honeymoon hotels.

Before my stepcousin got married in the Dominican Republic a while back, I flew in from London a few days early to get over my jet lag. I had found a great rate – almost too good to be true rate – at the Eden Roc Cap Cana. (Dominican resorts can be a very good value.) Well, I was the only single person there. The place was full of loved-up couples. So weird and awkward.

Never again. Now I carefully read the reviews and if it seems that the resort is more of a romantic destination, I steer clear!

To be clear, I can help you with a romantic trip if that’s what you want!! But if you’re traveling solo, let’s come up with something else! Let’s talk about your dream trip.

Mistake #9: Not packing essentials in my carry-on.

Two years ago, I landed in Amsterdam but my luggage didn’t. My AirTag very clearly showed that my bag was sitting on the tarmac in Newark.

The problem? I had a party to go to that night. Luckily, I had packed my cocktail dress in my carry-on just in case. But I had packed all my make-up in my checked bag. Time to go shopping! It was fun to buy all new makeup on the airline’s dime but it was also really annoying. I really didn’t have time to do that. So…pack the stuff you will definitely need in the 24 hours after your arrival in your carry-on bag!

Mistake #10: Not filing my insurance claim from Spain. YET.

When I was in Spain in March, one of our tours got cancelled because of heavy rain. We were already in the non-refundable period and the company wouldn’t give us our money back. The good news? I very quickly filed an insurance claim. I remember the rep I spoke to was so impressed that I was so on top of things. (Not my first rodeo!) But then…they’ve asked for follow-up documentation since and I haven’t taken care of it. I need that $250!! This is another benefit of a good travel agent. We will help you with your insurance claims…as long as you have all the docs ready!

I often joke that I have no problem admitting when I’m wrong. it’s just impossible to know everything and do everything right the first time. I hope you’ve enjoyed this latest installment of my really dumb travel mistakes. Remember, if you’ve got an entertainingly dumb travel mistake, contact me! I might feature your story in a later installment! And if I can help you avoid mistakes on your next trip, let’s talk! Book a complimentary vacation consultation here.

About Krista

I’m a Virtuoso luxury travel advisor based in West Palm Beach, Florida. Prior to moving to Florida to take care of my elderly mom with Parkinson’s Disease, I spent over 11 years living and working in London, England. My career and personal travel have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others as a Virtuoso travel advisor. I offer a 30 minute complimentary vacation consultation for anyone looking to plan their next trip.

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