Let’s be honest—buying travel insurance often feels like lighting money on fire. You shell out $50 to $100 for peace of mind, and then… nothing. No delays, no cancellations, no lost bags. Great news, right? Sure—until you actually need it and your claim gets rejected faster than you can say “nonrefundable.”
That’s exactly what happened to me. Multiple times.
Then I found the only travel insurance that actually paid me back. No drama. No 12-page PDFs. Just a super simple claim process and real cash in my bank account within a week.
The Backstory: A Flight, A Delay, A Mini Meltdown
I was flying from Chicago to Lisbon with a layover in London. Everything was going fine until my first flight got delayed… and delayed again… and finally canceled.
I missed my connection, spent the night in an airport hotel (out of pocket), had to rebook my next flight, and lost the first night of my Lisbon hotel booking. Total unexpected costs? About $420.
I had travel insurance. But I already knew how this story usually ends.
Spoiler: this time, it didn’t end in frustration.
What Made This Travel Insurance Different
I had signed up for SafetyWing, one of the newer players in the travel insurance game. A digital nomad friend had recommended it, and at first I was skeptical—it seemed too millennial and minimalist to be real.
But here’s what I loved:
- Monthly subscription model (you can turn it on and off) - Covers both medical and trip interruption/delay - Designed for long-term travelers, digital nomads, and spontaneous bookers - Super transparent claim process—they actually show you what’s covered in plain English - Coverage in over 180 countries
I paid $45 for a month of coverage. And then—surprise—I actually needed it.
How the Claim Process Went Down
No long phone calls. No getting transferred 12 times. Here’s exactly what I did:
1. Logged into the portal (yes, there’s an actual dashboard—not just a customer support email). 2. Uploaded proof of: - The canceled flight (screenshot and email) - My new flight receipt - The hotel booking I lost - The hotel I had to book in London 3. Wrote a quick summary of the situation.
That’s it. Within 72 hours, I got a confirmation email saying my claim was approved. Five days later, the money was in my account.
What They Reimbursed (and What They Didn’t)
They covered: - My hotel in London ($120) - The change fee for my new flight ($180) - 50% of my nonrefundable Lisbon hotel night ($60) - Meals during the delay (up to $60)
Total payout: $420
What they didn’t cover: - My Uber rides to/from the airport - The emotional stress of sleeping next to a vending machine (tragic, I know)
But honestly? Fair enough.
Why Most Travel Insurance Fails You
If you’ve ever filed a claim with one of the “big name” insurance companies, you already know the drill:
- Claims get denied for vague reasons - You need 12 documents you didn’t think to save - You spend weeks on hold - You realize the fine print excludes everything that actually happened
Most policies are written to sound generous but pay as little as possible.
What set SafetyWing apart (and others like it, like Faye or Heymondo) was that they were built with the traveler in mind, not the insurer’s bottom line.
When It’s Worth Buying Travel Insurance
Let’s be real—not every trip needs insurance. But there are a few times when it’s absolutely worth it:
- International travel (especially with connecting flights) - Trips involving multiple countries or long durations - Nonrefundable bookings like Airbnbs or small tour companies - If you’re carrying expensive gear (cameras, laptops, etc.) - During winter (snow = delays) or summer (storms = more delays)
Also, if you’re the kind of traveler who books flights impulsively and forgets to double-check baggage policies, insurance can save you from yourself.
Other Travel Insurances People Actually Like
- World Nomads – Good for adventure travel and short trips - Faye – US-based, app-driven, offers real-time claim processing - Allianz Global Assistance – More traditional, but solid for family or business trips - Heymondo – Gaining popularity for user-friendly digital claims
Do your homework, though. Every policy is different, and some only work well in specific regions or for certain trip types.
What to Check Before Buying
Don’t just click “Add Insurance” at checkout. Before you buy any travel insurance, ask these questions:
- Does it cover trip delays and interruption? - What’s the cap for medical coverage? (Look for at least $100,000 international) - Is COVID-related disruption covered? - Will they reimburse lost or delayed baggage? - How easy is it to file a claim? (Check real reviews, not just their website)
And maybe most importantly: what’s the deductible? That’s the amount you pay before they pay you. A $500 deductible on a $300 issue = no help at all.
