How I've Handled Travel Insurance (Long-Term, Multi-Trip) + Health Insurance (Globally)

When planning long-term, multi-trip travel, it took a while to determine which travel insurance I truly needed. And, now, I actually buy global (international) health insurance.

Since these two very different types of insurance are often confused with each other, I initially found it challenging to sort through all the options. I had to remind myself…

• travel insurance typically offers brief emergency assistance while traveling

• global (international) health insurance typically offers comprehensive healthcare around the world

And, because I like my travel to remain as fluid and flexible as possible (I love roaming free), it became clear that not all travel insurance or global health insurance could meet my needs.

In case anyone else has struggled to understand these insurance choices, too, I’m going to share how I’ve handled insurance along the way, and where I’m at right now.

What It Was Like Before Travel Insurance

First, I want to share a bit about what it was like before I had any (concept of) travel insurance.

My first year of frugal full-time travel occurred when I was a child. My dad took a sabbatical from teaching in public schools so we could travel educationally for a year.

We visited every historical site possible throughout North America.

We lived off of my dad’s small sabbatical stipend, a little savings, plus the work my parents found along the way (jobs they thought might be fun for short periods of time).

We still had my dad’s (public educator) health insurance, so I was able to have…

• an annual checkup before we left on our year-long trip

• an annual checkup when we returned from our year-long trip

While we were on the road that year, I experienced painful ear infections for the first time in my life—likely because my dad smoked cigars in the car for the first time.

My dad also quit smoking that year, after he heard a report on the car radio, which announced that smoking causes cancer. Yay, Dad!

So I had an emergency medical trip or two, plus I needed prescription meds. Back then, my dad’s health insurance covered all of our healthcare needs—at home and while traveling.

But things changed.

As a young adult, when I purchased my first plane ticket to Europe (in the days of Pan Am), airfare was very expensive, and I had no concept of travel insurance.

I assumed that if I became sick right before the trip, I would miss out on the trip and lose the entire value of my plane tickets. I had no idea that I could prevent that loss.

I also assumed that if I left on my trip healthy, I would remain healthy while on vacation. I had no idea what might happen if I needed emergency help or comprehensive healthcare abroad.

I had my first asthma attack on that trip, behind East Germany’s wall. I should have sought help, but I only took pills found over the counter, plus practiced calm, shallow breathing. I didn’t know better.

A few years later, when planning a prepaid package trip to another country, I (somehow) still had no concept of travel insurance. At this point, I cannot fathom why, but…

I thought if I couldn’t start or complete the trip for any reason, I’d lose the trip, lose the money prepaid, or incur extra fees to make changes (to return home early, let’s say).

Which is exactly what happened.

On that trip, even while taking every precaution possible, I became severely ill due to accidental exposure to contaminated water (back before I carried my water filter).

I couldn’t eat, drink, or find help to stop the severe symptoms ravaging my body, so I had to return home early to recover, which took weeks. That was when I began to think…

• how can I receive medical help while traveling?

• how can I protect myself financially while traveling?

Travel Insurance and Residency

After I began researching travel insurance, I started to see that it typically only covered brief urgent needs while traveling (not regular healthcare, not longer-term emergency healthcare).

Should I need rescuing or comprehensive healthcare after an emergency, it seemed travel insurance would stabilize me, then transfer me back home to my own state’s healthcare.

Those efforts and costs could be insurmountable.

That meant I’d need travel insurance that provided ample emergency transportation to get me back to my home state (it shocked me that some travel insurance policies didn’t offer much).

That’s when I also understood why travel insurance required me to have an annual health insurance policy back in my home state (to cover all my comprehensive healthcare needs).

But, since I no longer own a home in my home state, I first had to research what constituted legal residency in my home state to ensure I purchased all my insurance legally.

And, last I checked, I’m considered a resident in my state (no matter how much I travel) because…

• I have an address there

• I have my driver’s license from there

• I file taxes there

• I’m registered to vote there

• I’ve previously lived in homes there

• I still spend time there

• I use a sailboat there

That meant I could purchase an annual health insurance policy in my home state (even if I was gone much of the time and didn’t use it), which qualified me to buy travel insurance.

And, since my health insurance in my home state typically didn’t cover emergency care out of state, I needed travel insurance to cover medical emergencies wherever I roamed.

They worked together.

Travel Insurance for Single Destinations

Once I realized the importance of having travel insurance, I bought standard travel insurance that covered my travel to single destinations.

But I soon realized that was not best for me, because once I’m at a destination, I tend to roam a bit and head to another destination (like when in Sweden, on a whim, I sailed to Finland).

This would leave me uncovered due to deviating from my original plan, as I found that few travel insurance companies allowed one to buy coverage after leaving their place of residency.

So I had to look for a new solution.

Travel Insurance as An Annual Policy

I next purchased an annual travel insurance policy to cover all trips I might take during the year. I liked that I wouldn’t need to remember to buy travel insurance for each trip.

But I soon discovered most annual travel insurance policies (including the policy I purchased) seemed to have trip length limits. Those trip length limits were noted in the small print.

However, I didn’t read the small print before purchasing (I just asked the rep over the phone). It appears I misunderstood the interpretation of the plan, even though I asked specific questions.

So, at that time, the annual travel insurance plan worked well for multiple short trips throughout the year if…

• trips lasted less than 90 days

• each destination started and stopped from my place of residency

Meaning, I couldn’t travel longer than 90 days, and I’d have to return to my home state after each trip before leaving for another destination.

That would definitely be a more expensive, less convenient, and less sustainable way for me to travel. I’d have to spend a lot more time on flights.

I had to find better travel insurance for my travel needs.

Travel Insurance for Multiple Destinations

After much comparison research, I finally found travel insurance that covered multiple destinations (in the USA + internationally), for short- and long-term travel, with the flexible options I needed.

I loved having that insurance—World Nomads.

As an affiliate, we receive a fee when you get a quote from World Nomads using this link. We do not represent World Nomads. This is not a recommendation to buy travel insurance.

I loved using World Nomads for years because their travel insurance allowed me to…

• visit multiple destinations without having to return home between destinations

• purchase/repurchase while traveling (so I could roam free/travel indefinitely)

• purchase USA + international coverage (more than 100 miles from home)

• travel short- and long-term (I usually purchased 1-3 months at a time)

• have emergency medical for accident or sickness (at least $100,000)

• have emergency evacuation (at least $300,000)

• pay a reasonable monthly rate at that time

• always read the small print … as … insurance coverage can change at any time

To give an idea of how well World Nomads worked for me while traveling North America, I’ll share what happened after an urgent care + ER visit (after-hours) at a mountain town hospital.

Examined for quite a long time in the urgent care clinic, lab work was completed in the urgent care clinic plus in the hospital’s ER (down the hall, across the drive, through the ER entrance).

Emergency room bills in the USA would frighten anyone. And multiple bills were generated from this emergency care visit, with one bill arriving a year later.

The urgent care clinic and hospital first sent those bills to my home state health insurance, but that insurance wouldn’t cover everything because my emergency happened out of that state.

So I gathered all the clinic and hospital bills, my home state insurance responses, plus receipts for anything I’d paid out of pocket, and sent copies of it all to World Nomads.

I also told World Nomads that all bills might not yet be in.

I waited patiently during World Nomad’s billing reimbursement process, which took a while (I found this to be just like any other USA insurance timeframe, so I chose patience).

World Nomads covered everything my home state health insurance would not. Even a year later, when the final bill finally arrived. I felt grateful.

I didn’t have to pay thousands of dollars for urgent/ER care (like the time in my past when I didn’t buy travel insurance, then traveled across state lines by auto, and ended up in an ER).

To give you an idea of how well World Nomads worked for me internationally, they were the only travel insurance I could find during the pandemic that was offering pandemic coverage.

I could buy/extend my World Nomads travel insurance coverage when it seemed nobody else was able to assist with pandemic coverage. That felt so reassuring to me while caught overseas.

Travel Insurance With Different or More Benefits

Importantly, many have wanted travel insurance with different or more benefits than what I chose for myself. Those plans now appear to exist. Maybe they’re even becoming more hybrid.

While researching them, I found my legal residency, travel destinations, age, medical needs, and other personal details so important to weigh when considering these travel insurance decisions.

Everyone must carefully choose what works best for their situation.

Two insurance companies came closest to meeting such needs, but I had additional requirements that meant I had to pass. However, many nomads have shared that they find them a perfect fit…

• Genki

  As an affiliate, we receive a fee when you sign up for Genki using this link. We do not represent Genki. This is not a recommendation to buy travel insurance.

• SafetyWing

  As an affiliate, we receive a fee when you sign up for SafetyWing using this link. We do not represent SafetyWing. This is not a recommendation to buy travel insurance.

Air Ambulance Annual Membership

I should note that when I’m traveling or living in the Pacific Northwest Region of North America, I purchase two affordable air ambulance annual memberships.

Most people likely don’t, but I think it’s super important. They cover potential emergencies while I’m traveling or living in more remote areas of the Pacific Northwest.

• I purchase an Airlift NW annual membership when I travel or live between Washington and Alaska

• I purchase a Life Flight annual membership when I travel or live in Washington, Idaho, Montana, or Oregon

This is because I’ve been quoted $7k to $10k per emergency flight, and I imagine it might even be higher. I’ve also heard of insurance policies that did not cover the expense of those flights.

The goal, for me, is that if ground medics, the ER, or doctors need to put me in an air ambulance, they’d make that call, but I’d not pay that extremely hefty bill.

If travel insurance or health insurance claims to cover these flights, I still always buy these annual memberships, as I don’t want to take a chance on ever receiving one of those bills.

Global Health Insurance

I’ve always wanted a global (international) health insurance policy. I just never imagined I would need one in the unexpected way that I have.

I thought I would eventually buy a global health insurance policy down the road, when I was fully retired and no longer spending as much time in my home country.

But last year, I received a letter informing me that I was losing my affordable healthcare (in the state where I’m a legal resident). I could not believe what I was reading.

The letter urged me to use my health insurance while I still had health insurance (the last two months of 2025, exactly when it’s difficult to book healthcare appointments).

What about after that? The letter literally warned me again in a serious tone that, after that, I would no longer have any affordable healthcare.

Millions of us with our legal residence in the USA received such letters.

We are employees whose employers do not provide affordable health insurance. Or we are self-employed. Or we are retired, yet too young to sign up for Medicare.

So, we are the people who have to purchase our own healthcare (since we could not rely on an employer to offer that benefit).

During the last four years, our health insurance was at its most affordable. Now it’s gone.

Can you imagine receiving a letter that tells you you will no longer have affordable healthcare? Imagine all the young families in this situation. Parents with young children. Imagine the elders.

It is psychopathic to take away healthcare from millions of citizens.

To make matters worse, based on the best available data I could find, it appears there are not enough jobs in the USA that provide affordable health insurance.

So we can’t solve this inhumanity by asking everyone to seek new employment that has better healthcare benefits. The data appears to show that not enough exist.

This means it appears there is no way to ensure all US citizens have affordable healthcare. Does that make sense? No.

Instead, we’re offered 2026 health insurance options with unaffordable premiums, unaffordable deductibles, and poor coverage.

What do I mean by unaffordable?

The only health insurance available for me to purchase now in the US takes 30-50% of my annual income before any health coverage even begins. And I’d still have additional healthcare costs.

Every single year. That is not affordable. This is not sustainable.

So, instead of spending the last of 2025 trying to book healthcare appointments, I actually needed to spend that time seeking and researching all health insurance options.

I was not going to pay 30-50% of my annual income to an insurance company that would not provide any health coverage until after they received 30-50% of my annual income.

This meant I would no longer buy health insurance in my state.

I also wasn’t willing to go uninsured. In the States, I could quickly lose every single thing I’ve spent my life saving.

So what was my solution?

I decided to prioritize international travel in 2026 and buy a global (international) health insurance policy. I decided I’ll roam free, internationally, where I’ll obtain my healthcare.

The first place I looked for that global (international) health insurance was where most other nomads I know go to review and purchase nomadic insurance…

• Genki (for those over 55, Genki says to ask about their Genki Resident)

  As an affiliate, we receive a fee when you sign up for Genki using this link. We do not represent Genki. This is not a recommendation to buy insurance.

• SafetyWing

  As an affiliate, we receive a fee when you sign up for SafetyWing using this link. We do not represent SafetyWing. This is not a recommendation to buy insurance.

I seriously considered Genki and SafetyWing. Many nomads share how much they love them. Due to my age and needs, though, I realized I needed slightly different coverage at this time.

After investigating every other option I could find, I realized I wanted global health insurance that allowed some flexibility + US healthcare coverage when I’m in the States.

The following is where I went and what I chose…

• International Citizens Insurance helped me review (in detail) my best options

• CignaGlobal is the global (international) health insurance I chose

Every situation is unique. Everyone must do their due diligence. Everyone must cross-compare every single detail that matters to them. We all deserve the best healthcare.

I truly feel so grateful for the relief I now feel.