Travel Experiences I Probably Shouldn’t Have Tried

Some trips are life-changing. Others… are life-questioning. I’ve made travel decisions that could be categorized somewhere between mildly irresponsible and what were you even thinking? So today, I’m baring my soul and recounting the travel experiences I probably shouldn’t have tried — and of course, throwing in some tools so you can do them smarter than I did

Melissa Ridge

5/12/20252 min read

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Introduction: When Good Travel Ideas Go Bad

Some trips are life-changing. Others… are life-questioning. I’ve made travel decisions that could be categorized somewhere between mildly irresponsible and what were you even thinking? So today, I’m baring my soul and recounting the travel experiences I probably shouldn’t have tried — and of course, throwing in some tools so you can do them smarter than I did.

The Tuk-Tuk Drag Race in Bangkok

What started as a casual night turned into a tuk-tuk drag race through the streets of Bangkok. Would I recommend it? Absolutely not. Did I feel like Vin Diesel in a three-wheeled tin can? Absolutely yes.

Travel smarter:

Book a proper transfer next time with KiwiTaxi or GetTransfer.

The Sketchy Boat Ride in the Philippines

The boat had one life vest. The captain was half asleep. And yet, I still climbed in. Learn from my questionable judgment.

Pro tip:
Check out legit boat rental options through SeaRadar for safe, reputable charters.

Renting a Scooter in Bali Without a License

I thought I was a natural. Bali traffic said otherwise. 10/10 would not recommend — unless you like gravel rash.

Get legit with BikesBooking — international rental options with insurance, helmets, and zero judgment.

Spending a Night in an Airport Because I Missed My Flight

Nothing says "travel pro" like sleeping on your luggage under a flickering airport light.

Hack it like a boss:

Book flexible flights with WayAway
Store your bags at Radical Storage and go explore

Essential Travel Tools (That Would’ve Saved Me)

VisitorsCoverage Travel Insurance — because accidents will happen
Airalo eSIM — stay connected so you can call for backup
EconomyBookings for reliable car rentals
Trip.com for hotel deals I actually trust
Tiqets for ticketed attractions (no sketchy vendors)

Bonus: My Millionaire Dating Mishap

Yes, I once matched with a millionaire on vacation. No, he wasn’t as advertised. I’ll leave it at that.

Curious?
Check out Millionaire Match — but proceed with caution (and maybe a prenup).

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Closing Thoughts

Travel isn’t always picture-perfect — and honestly, the disasters make the best stories. Just make sure your disasters come with insurance, a reliable scooter, and a backup hotel plan.

Safe travels (mostly)!