🐰 ChatGPT Almost Ruined Her Trip To See Bad Bunny 🐰
Published: Mon, 02/16/26
Updated: Mon, 02/16/26
AI is great for travel. Until it isn't. Here's how to use it safely.
ChatGPT Almost Ruined Her Trip To See Bad Bunny
I’m watching the Winter Olympics.
Figure skating, speed skating, bobsledding, you name it.
I
don’t usually watch Olympic sports, but this time my eyes were glued to the TV. I was yelling at the screen like I had trained for years.
“Next up: curling!”
Their stares are so intense. The sweeping. The strategy. The drama.
But after two straight hours of Olympic glory, it hit me.
I’m not watching for the love of sport.
I’m using the Olympics to procrastinate on writing this newsletter.
Touché, Subconscious Andrew. 😉
ChatGPT is a great tool. I use it all the time.
But it can get you in trouble if you're not careful.
A Spanish TikTok content creator with close to a million followers learned this the hard way. She was planning a trip to Puerto Rico with her boyfriend to see Bad Bunny in concert. Before the trip, she asked ChatGPT whether or not she needed a visa to enter the country.
ChatGPT told her she didn't.
And technically, that was correct. European citizens don't need a visa to travel to the U.S. for tourism under 90 days. But what ChatGPT left out was that she still needed ESTA approval. That's the Electronic System for Travel Authorization, and without it, you're not getting on the plane.
So when she showed up at the airport, she was denied
boarding.
She posted a video in tears, walking through the terminal after being turned away. Eventually, she and her boyfriend got the ESTA sorted out and made it to Puerto Rico in time for the concert.
But here's the thing.
We already deal with enough inconveniences when we
travel. Delays, cancellations, lost bags, long lines.
The last thing you need is a preventable problem caused by trusting AI without double checking.
So here's how I use AI for travel without getting burned.
Always ask AI to cite
its sources. If AI tells you something that could have a major impact on your trip, financially or logistically, ask it one simple question: "Where did you get that information from?" Then visit the original source yourself and verify it. For travel requirements, that means going directly to the government website for the country you're visiting.
Understand that AI lies differently
than people do. When a person lies to you, it's usually easy to spot. Something feels off. But when AI gets it wrong, it sounds completely confident. They call it "hallucinating." AI will give you a wrong answer with the same tone and certainty as a right one. That's what makes it tricky. You have to stay skeptical even when the answer sounds perfect.
Use AI to skim, not to decide. I use AI to quickly get the lay of the land. What documents might I need.
What the weather looks like. What neighborhoods to stay in. But I always do further research on my own. AI models change constantly. The algorithms get updated. So the responses you get today might be completely different from what you'd get next week. So use it as a starting point, not the final word.
AI should complement your trip planning, not replace it. Think of AI as a research
assistant. It can save you hours of digging. But the final decisions, especially anything involving visas, entry requirements, or money, should always go through an official source. Government websites, embassy pages, airline requirements. That's where the truth lives.
The truth is, AI is only as useful as the person using it.
If you hand over all your decision making to a chatbot, you're rolling the dice. But if you use it as one tool in your toolkit and verify what matters, it can genuinely make your travel planning faster and easier.
Keep traveling,
Andrew
Have you ever gotten bad advice from AI? What
happened?
Cocktail of the Week
Planter’s Punch is believed to have originated in Jamaica in the late 1800s, where rum punch was a staple on sugar plantations. The earliest known written recipe appeared in a London magazine in 1878, labeled as “Planter’s Punch,” linking it directly to the tropical flavors of the Caribbean.
Ingredients: • 2 oz dark rum (preferably Jamaican) • 1 oz fresh lime juice • 3/4 oz simple syrup • 1/4 oz grenadine (optional, for color) • 2 dashes Angostura bitters • Splash of club soda (optional) • Garnish: orange slice and cherry
How to Prepare: • Fill a shaker with ice. • Add the dark rum, lime juice, simple syrup, grenadine, and bitters. • Shake well until chilled. • Strain into a tall glass filled with ice. • Top with a splash of club soda, if desired. • Garnish with an orange slice and cherry.
Random Travel Thought
The best travel companions are both easy to talk to, and easy not to talk to.
Follow me on Instagram.
The Plug
Cheap flights:
Going.com: This might be the only discounted flights website you need.It’s a paid service that sends you notifications when deals become available, but they expire in a couple of days so Act Fast!!
Secret
Flying
🤫: This website emails you about free flight opportunities and even better… it doesn’t cost a thing!!
Skyscanner
:
An older, but still reliable website that’s also *FREE* so there’s no reason not to use it. Use the "Explore the World" feature and set your departure date to "Whole Month" to find the cheapest deals.
Insurance:
Safety
Wing
:
I use Safety Wing as my travel insurance because the plans are flexible. You can easily insure a 1-week trip for like $11 dollars which is less than the cost of a cocktail at the bar.
Travel Gear
Compression socks: Sitting for extended periods of time is not good for the body, so keep yourself healthy enough to go on more trips.Link
Apple AirTags: Consider getting Apple AirTags for the peace of mind of always knowing where your luggage is. Link
Smart Phone holder: It's a foldable sheet that can be used as a stand for your iPhone or iPad.Link
Packing cubes: Having a separate container works wonders for keeping
clothes wrinkle-free. It also makes packing/unpacking much easier.Link
Donut Power Strip: Power outlets are always in demand, but sometimes they're in weird spots. I use this bagel because it's lightweight, and I don't have to think about it.Link
Travel Case Organizer: Cable organizers can be a pain, but this is what I use to keep my cables organized. Link
Backup batteries: I like these backup batteries because they have three important components for me: 1. They have enough power to recharge my phone multiple times at once, 2. Are small enough to put in my pocket, and 3. Are sturdy enough to survive a fall. Link
Yoga Mat: I use this thin mat to get my stretching in even when I'm traveling. Link
Jump Rope: It's so easy to bring a jump rope with you for exercise because it
weighs almost nothing and takes up no space. Link
Liquid IV: Great for hydration to keep you from dying. When you're traveling, it's time to live it up! Link
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