Why I Finally Got Travel Insurance (And Why SafetyWing Won)

I Traveled for 20 Years Without Insurance

I’ll be honest — for most of my adult life, I never once thought about travel insurance. Solo trips to Mexico, weekend flights to random US cities, flying around Southeast Asia after I got my passport 23 years ago. I was young, healthy, and invincible. Insurance felt like something my parents would buy. A waste of money on something that would never happen to me.

And for years, nothing did happen. A missed connection here, a dodgy stomach there — nothing that couldn’t be fixed with patience and Imodium. I figured I’d just keep rolling the dice.

Then the Math Changed

Getting older shifts your perspective. Having a family shifts it even more.

When we started taking our toddler to places like Siquijor, it hit different. Beautiful island, but the nearest serious hospital is a ferry ride away in Dumaguete — and the nearest great hospital is Chong Hua in Cebu, another flight or overnight ferry on top of that.

A medical evacuation flight from a remote Philippine island to Manila or Cebu starts at $10,000 USD. A single hospital stay abroad without insurance can run $20,000–$50,000. One bad scooter accident, one allergic reaction, one fall on a waterfall hike — and you’re looking at a bill that could wipe out your savings.

When it was just me, I could absorb that risk. With a family, I couldn’t. The stakes were too high and the cost of coverage was too low to justify skipping it.

What I Was Looking For

I spent a few weeks researching travel insurance before our next trip. My requirements were specific because of how we travel:

• Buy while already abroad — We sometimes extend trips or book last-minute. I needed a policy I could activate from anywhere, not just from home before departure.
• Covers the whole family on one plan — Adding a spouse and child shouldn’t require three separate policies and three separate claims processes.
• Works for multi-destination island-hopping — We don’t fly to one resort and sit there. We hit 3–5 islands per trip with ferries, domestic flights, and bangka boats in between.
• Affordable for frequent travelers — We go to the Philippines multiple times a year. Annual policies were either expensive or had too many restrictions.
• Flexible dates — No locked-in departure and return dates. We change plans constantly.

Most traditional travel insurance failed on at least two of these. World Nomads was close but expensive for families. Allianz required buying before departure. IMG had complicated claims processes.

What We Ended Up With

After comparing a dozen providers, we landed on SafetyWing’s Nomad Insurance. Here’s why it fit how we travel:

• ~$56 USD per 4 weeks — auto-renews every 28 days, cancel when you’re home, restart when you leave.
• You can buy it while already traveling — most insurers require purchasing before departure. We’ve signed up mid-trip.
• Covers 180+ countries — one policy works wherever we end up.
• Family-friendly — one child under 10 is covered free per adult.
• Simple online claims — submit through their app or website.

We’ve used it for every Philippines trip since.

What It Covers

For reference, here’s what’s included on their Nomad Insurance plan:

• Medical & hospitalization — up to $250,000.
• Emergency medical evacuation — up to $100,000. This is the one that matters on remote islands.
• Emergency dental — up to $1,000.
• Lost checked luggage — $500 per item, $3,000 max.
• Travel delays — $100/day after a 12-hour delay, up to 2 days.
• Trip interruption — up to $5,000.
• Political evacuation — up to $10,000.
• Leisure sports — up to $250,000 for surfing, snorkeling, hiking injuries.
• Motor vehicle accidents — up to $250,000. Relevant if you’re renting scooters.

What It Doesn’t Cover

I’m not going to pretend SafetyWing covers everything. Here’s what’s excluded on the Essential plan:

• Pre-existing conditions — If you have a known medical condition, it’s not covered. This is standard across most travel insurance.
• Maternity & pregnancy — Not covered on the Essential Nomad plan. They have a separate Remote Health plan for long-term expats that includes this.
• Cancer treatment — Not covered on the Essential plan. Again, the Remote Health plan is the option for this.
• Extreme sports — Professional or competitive sports, skydiving, bungee jumping. Leisure versions of most activities (surfing, snorkeling, hiking) are covered.
• Deductible — There’s a $250 deductible per policy period. So small claims under $250 come out of pocket.

None of these were dealbreakers for us, but worth knowing before you buy.

We’ve Thankfully Never Used It

In all our trips with SafetyWing coverage, we’ve never filed a claim. And that’s exactly the point.

It’s one of those things where you hope you wasted your money. But if something does go wrong on a remote island, you don’t want to be figuring out how to pay for a medevac flight while it’s happening.

Whatever provider you go with, just get something before you fly — especially if you’re hitting remote islands. Our Philippines Travel Essentials guide covers the rest of the practical stuff: visas, ATMs, transport, packing, and cultural etiquette.