Funny Travel Stories

7 Travel Tips to Avoid Funny Travel Stories

I recently laughed so hard with my best friend when I realized a huge travel mistake I had made; something that to me seemed so out of place that it felt like I was telling a travel joke instead of a funny travel anecdote. My funny travel stories had previously involved my dad making booking mistakes, or some fall from a canon. Never had they involved me getting to the airport and missing a flight. 

Following these travel tips will help you have positive travel experience stories. But honestly, when things go wrong and you can laugh about it, they become the best travel tales.

Travel Tip #1: Check the Date and Time

This short travel story started with me asking my husband for a separation. In the midst of the chaos and him leaving Rome for Mexico, I decided to visit my best friend in Barcelona. Aline sent me a screenshot of the ticket she was about to buy, from Saturday to Wednesday, as I was supposed to move back to Mexico on Friday. I approved the selection, she bought it, and I packed. I checked in the night before, and made sure my dogs were taken care of. The next day I headed to the airport, a little later than planned. 

When I got to the airport with only my carry-on bag and 35 minutes until the gate closed, I headed directly to the security checkpoint. The electronic machine marked a big fat red X and told me to see an agent. I obediently went to stand in line at the Ryan Air counter, while one of the only two ladies available left. My heart was racing as I kept looking at the clock. A man, Italian, loud, and rude, arrived with an airport employee and cut ahead, screaming at the lady and taking a whole 10 minutes of my precious time.

By the time I arrived to the counter it was 8:02 and my flight closed at 8:05. The lady asked me what was wrong, I told her, she continued asking if the machine had said anything else. No. She then scanned my ticket and told me the problem was that the gate had closed. I complained and told her I had arrived earlier. 

“Where were you then?”

“In line, waiting for you.”

She didn’t say anything else, except to wait for the ticketing agent who arrived in an hour to change my ticket. I didn’t panic but went into action mode. Aline texted me she had dreamt I missed my flight. Yup, I told her I would let her know about my next flight. I searched for other flights, just one more on Alitalia that left in 35 minutes. I was already at the airport. Click, bought. Tried to check in: check in closes 40 minutes before the flight. 

Shit. 

I stopped running around, grabbed a cab home, and bought a ticket from Sunday to Sunday, extending my stay. I wasn’t going to let my anxiety get out of control, so I breathed deeply and chucked my lack of attentiveness to depression. My parents called to bother me about missing the first flight in my life. We all had a laugh about it. I have always been super responsible, a perfectionist, and even flew more than 100 segments in a single year most of them as a solo female traveler, and had never missed a flight. EVER. But I also know to laugh at travel mishaps and be flexible when I travel. I need a good amount of travel humor to keep my anxiety under control.

I was having an amazing time in Barcelona, when I get an email on Friday to check-in for my Ryan Air flight the next morning. Laughing so hard, I handed over the phone with my ticket on it so Aline could check the date. I did in fact not miss my flight, but instead arrived A WHOLE WEEK early. That is why the machine didn’t let me through. After laughing for ten minutes straight, I immediately called my family to let them know this funny travel story, that I in fact had not MISSED my flight.

Travel mishaps may lead to amazing trips

Travel Tip #2: Double Check the Year 

This travel mistake is only second to my dad’s one a couple of years ago. This story is our favorite funny Christmas story and we don’t let him live it down. 

The best travel stories starts with a mistake, like mixing up the year on your reservation

On December of 2015 we were supposed to embark on a cruise ship that circumnavigated New Zealand, leaving from Auckland and disembarking in Sydney, Australia. Our flight tickets were booked arriving to Auckland leaving from Sydney. My dad kept pestering us to look at the tour options to chose from. No one could find the cruise and there were no options, even as late as November. Only when my dad provided the link could we find the cruise, but no updates. A week before we were set to leave, my brother’s ex called my dad to tell him something was wrong with the cruise reservation, it said there were still 370 days to our cruise. 

Instead of booking the cruise for December 2015, my dad booked it for December 2016! 

We laughed it off as we planned activities in Auckland and Sydney for our impromptu land-locked trip. He got a whole refund as it was a year in advance, and so we set out to Auckland. 

I think my dad, the smartest, most dedicated man I know, has booked the most wrong date trips ever. It’s not because he doesn’t pay attention, just has so much on his plate. 

Again, we laughed off this funny incident and had a blast in New Zealand, visiting Hobbiton, Waitomo Caves, Waiheke Island, abseiling in Piha, and eating delicious food. 

Travel Tip #3: Always Check Visa Requirements 

On December 22, we packed our bags, said goodbye to the hotel staff, and headed to the airport for Sydney. 

Everyone was so excited to visit Australia for the first time. But, then some dreaded words came out of the agent’s mouth, “Where are your visas?”

Because of a missing visa, I got to see Hassel!

Blank stares. We need visas? 

Most of us had passports on which we could get online visas, but my mom and grandma couldn’t. Change of plans, once more. 

We headed back to the hotel, greeting the staff, laughing, and asking for our rooms back. Meanwhile my sister’s ex was complaining about the change of plans, and my ex calling from the US making a huge deal about it. The rest of my family just tried to make things work. 

Traveling to Australia was out of the question for my mom and grandma as the consulate was closed for the holidays. So instead we headed to Christchurch for a zip line trek and a haunted mansion on Christmas Eve. I even got to see one of my best friend’s from boarding who I hadn’t seen in years! On Christmas day, the family separated into two groups, those leaving for Sydney to catch our flights back and those staying in Auckland with a new flight back home. 

Always check visa requirements. Do not assume that because you can go into one country (New Zealand) without a visa, you can go into another (Australia) without one. 

Travel Tip #4: Double Check the Weather 

When you think of Hawaii, don’t you picture Luaus on the beach, sunny white beaches, bathing suits, and snorkeling? 

We did, too. That is until we arrived to the wettest, coldest side of the Big Island. The west side or Kona is where the Hawaii of my dreams was, the east side or Hilo was the one my dad chose for our eco-adventure filled with walking on lava, zip lines, volcanoes, hiking, and being cold in short shorts. 

It was an amazing vacation, one that I cherish to this day because of the memories, the places we visited, and the anecdotes. We went to see Les Miserables in a small theatre that wasn’t sound proofed so we could hear the whole gun scenes from the movie next door. Or the time we took the longest route to the green sand beach through dried lava in a 15 passenger van with a 3 month old, only to realize there was a highway on the other side – I’m glad my dad always gets the rental insurance!

We did have to buy some warm clothes and a waterproof jacket. The first pictures of the vacation, I’m standing in a short short and tank top, freezing my ass off as my dad had not informed us that we were not going to use our cute dresses and bikinis. Always double check the weather of your travel destination, so you don’t look like my grandma trying to reduce the weight of her bags for a Ryan Air flight, wearing everything she owns. 

Funny travel story Picture of when we went to Hawaii and needed warm clothes even to walk on lava

Travel Tip #4: Do not climb objects or trees with your sister

My sister and I tend to climb stuff and get stuck, they make for pretty funny travel moments. On my sister’s XV birthday trip to Ireland we went on a hike and found this tree with amazing climbing branches. I decide to get up on the tree and get a cute picture for my album – this was before IG – but hadn’t realized that this particular branch had another smaller branch coming from it an an angle. My butt wasn’t as big as it is now, but that didn’t stop it from getting stuck. I could not move forward or back, I couldn’t turn, so of course I decide that my way to get down is like a scared cat holding on to dear life rotating until I was hugging the branch facing up. Then I was able to let go. 

Why not, my incredibly smart, over achieving sister climbs the tree in exactly the same way – I promise she is smart- and gets stuck… for longer than I did. In the meantime there are other tourists passing by, taking photos of her stuck in a tree while we film her and laugh. She eventually discovered that the only way to get down from that position was, in fact, my panda cling. 

There are other times when I swear that those who try to help sometimes end up pushing you over the edge. There wasn’t any edge as it was the barrel of a canon, but as I was trying to climb a canon for again a cute picture on top of it – this time for Instagram – my amazing sister decides to help me up by pushing my legs over the canon. Again, I used my cat cling to hold on for dear life while I laughed and my mom filmed. 

So if you have a sister like I do, avoid climbing stuff for that picture unless you are okay with your funny travel video being played by the family multiple times. 

Travel Tip #5: Always keep your bag with you, unless you are clumsy

On our trip to Costa Rica, we did not do the thermal pool fancy spas. Instead, we followed our guide down to the side of the highway and entered the river from an underpass. Here the water barely reached our ankles. From there we walked up the river, past a little wall that made a super slow waterfall into a beautiful area with less people, more nature, and some candles our guide had brought. After enjoying the nice warm water in darkness, we headed back to the underpass. I had mine and my ex’s things in my backpack, my sister had hers in our friend’s backpack. Mid walk, my sister decided to carry the backpack back right before the knee high wall. 

As our friend swings one leg over, she immediately swings the other one without properly stepping down first, making her dive into the cemented river like an ungraceful penguin on the ice. I stepped out of the way as she kept sliding further down, until she finally stopped. It was definitely one of the highlights of the night as her funny fall makes us laugh especially because the cameras, clothes, and phones were kept dry by my sister. If you have a clumsy friend with you, never trust your bag to them! 

Travel Tip #6: Whatever you do, do not get on a bike 

It might seem like a great idea with your Oxford Summer School crew to rent some bikes to go to Woodstock along the River Thames, but it isn’t, trust me and Lauren. There was a sort of Elvis convention as the boat houses were filled with Elvis impersonators as we rode along. Some ten minutes into the drive, I start to lose control of the bike. My two options were, falling into the river or into the bushes – I had my period so the bushes it was. 

After a bit of commotion, I managed to stand up, hold back tears and embarrassment as I picked out thorns from my left arm and left leg. I brushed dirt off my shorts and got back on my bike, prideful as ever as I assured everyone I was in fact ready to continue on. I managed to make it to Woodstock and back without any other complications – or falls! My family now makes fun of me every time I get on a bike! 

A couple of years after this incident, on that same fateful trip to Costa Rica, we rented some bikes. I was determined to not fall this time, and our small group managed to stay on our bikes the whole time, that is until the end. When turning on the street where we were supposed to return our bikes, my friend started zig zagging. Her feet down, trying to catch herself, she was stopped by a parked car. She looked at the guide in horror as he hurried towards her to check on the car. No scratches. He told her to not look back and ride as fast as she could. We didn’t look back. 

Travel Tip #7: Learn to laugh at yourself and be flexible 

Something I’ve learned over the years and through all of these experiences, is that you need to be able to laugh at yourself and your misery. Sometimes it’s all you can do to keep yourself from crying, or to not ruin an amazing trip. I have anxiety, so I know how hard it is for things to not go as planned, for little things that seem to ruin a trip, when in reality they just make for the best travel anecdotes. Even if you can’t laugh at them today, maybe you can in a couple of days or months, or at least learn something. 

Breath deeply, maybe you didn’t get on THAT flight for a reason. Maybe not being able to go to Australia led you to Queenstown and to one of the best family experiences (and pictures) as we all, even my grandma, headed into a haunted house! And, actually, missing out on those days in Sydney allowed me to see one of my best friends from boarding school who I barely see on Christmas Eve. 

You cannot connect the dots unless you look back, so remember that when you are freaking out about something going wrong. Maybe it’s for the best, even if it isn’t, if it’s out of your hands go with the flow! 

Haunted house on Christmas Eve because of a mistake became an amazing funny travel story

Follow these tips or be prepared to tell your funny, sometimes embarrassing, travel stories to your friends. Or even better, they will remind you of them, constantly. 


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