Travel Regrets: 10 Things I Wish I’d Done Differently on My Trips

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Confession Time: I’ve Messed Up on Trips… a Lot

Listen, I love travel as much as the next adventure-addicted Sagittarius, but let’s be real — not every trip is flawless. Between missed flights, tragic hotel choices, and that time I tried to ride a camel in skinny jeans, I’ve gathered enough travel regrets to fill a carry-on.

Here are the things I wish I’d done differently — and what I’d recommend for you so you don’t make the same questionable choices. Because what are friends for if not to save you from $14 airport sandwiches and sketchy hostels?

1. I Wish I Booked Airport Transfers Ahead of Time

There’s nothing quite like landing in a new country, phone dead, no Wi-Fi, and some random man aggressively offering you a “good price taxi.” Avoid my rookie mistake.

Fix That:
Pre-book your airport transfer here.

2. I Regret Not Having Travel Insurance (That One Time)

Nothing says “learn your lesson” like losing your luggage and having food poisoning in Bali with no backup plan. Don’t be like 2018 me.

Get Covered:
Quick, reliable travel insurance here.

3. I Should’ve Rented a Scooter

I once walked 6 miles in 90-degree heat because I didn’t realize renting a scooter was that cheap and easy. My thighs have never forgiven me.

Pro Move:
Book your ride ahead of time.

4. I Didn’t Pack a SIM Card or Wi-Fi Solution

Imagine trying to use Google Maps by memory in Tokyo. Yeah… don't.

Stay Connected:
Grab a travel SIM here.

or

Go for a pocket Wi-Fi.

5. I Waited Too Long to Buy Event Tickets

I missed a concert in Rome because I assumed tickets would be available at the door. Spoiler: they weren’t.

Lesson Learned:
Book your tickets early.

6. I Skimped on Accommodations Once… Never Again

Turns out, a $12/night hostel with “character” means zero Wi-Fi, mystery stains, and a friendly rat named Larry.

Book Smart:
Find good hotel deals here.

7. I Didn’t Use a Luggage Storage Service

Dragging my suitcase through cobblestone streets for 4 hours before check-in was peak regret.

Avoid This:
Use Radical Storage.

8. I Flew Without Checking for Cheaper Flights

I once booked a flight, then found the same one for $200 less an hour later. Cue rage.

Never Again:
Use this flight deal finder.

9. I Should’ve Taken More Road Trips

There’s something glorious about renting a car and hitting the open road — preferably with snacks and a killer playlist.

Next Time:
Compare car rentals here.

10. I Wish I Had A Millionaire Travel Buddy

Hey, can’t hurt to dream big.

Shoot Your Shot:
Date a millionaire traveler here.

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Final Thought: Regret Less, Travel Smarter

Travel regrets are inevitable, but you can dodge a lot of rookie mistakes with the right planning — and a little sass. Use my regrets as your cheat sheet, book smarter, stay connected, and chase those adventures like the travel-savvy badass you are.

P.S. If you book anything through the links above, I’ll toast you with a street food snack on my next trip. Appreciate you!