How I Handle Travel Insurance (for Multi-Trip + Long-Term Stays)

When I began planning for long-term travel (and multi-trip stays), I slowly learned why travel insurance was one of the most important responsibilities I needed to comprehend.

But travel insurance was also, initially, one of the most confusing topics for me to grasp, because I like my travel plans to remain as fluid and flexible as possible (I love roaming free).

In case anyone else has been confused about travel insurance, too, I’m going to share how I’ve handled both my health and travel 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 full-time travel occurred when I was a child. My dad took a sabbatical from teaching so we could travel for a year (we only had his work health insurance), so I had…

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

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

While we were on the road that year, I had extremely painful ear infections for the first time in my life (my Dad smoked cigars in the car for the first time—he also quit that year).

So I had an emergency trip or two plus I needed ear infection medicine. Back then, my dad’s health insurance covered all 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 expensive, and I had no concept of travel insurance.

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

I also assumed that should I get sick right before the trip, I would miss out on the trip and lose the entire value of my plane tickets. Thank goodness that didn’t happen—until later.

(I had my first asthma attacks on that trip, behind East Germany’s wall. I should have sought help, but I only took OTC drugs while practicing calm, shallow breathing. I didn’t know better.)

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

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

Which is 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 proper medical help while traveling?

• how can I protect myself, financially, while traveling?

How Residency Impacts Travel Insurance

Since I no longer own a home or auto, I’ve had to research what constitutes legal residency in my home state to ensure I handled my health and travel insurance legally.

Last I checked, I’m considered a resident in my home state (no matter how much I travel) because of the following…

• I keep 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 boat there

That means I’m also required to buy private US state health insurance to cover me in that state. So I purchase annual healthcare insurance through that state’s healthcare system. It covers…

• annual checkups in that state

• preventive care in that state

• specialist care in that state (including acupuncture)

• free online TelaDoc appointments (so convenient)

• emergency care in that state

• essentially all my healthcare needs while in that state

• a minimal amount of emergency care outside that state

Since my private US state health insurance only covers some emergency care out of state, I need travel insurance to cover medical emergencies wherever I roam (so I don’t receive another ER bill like the time I traveled across state lines by auto, without travel insurance, and had to pay nearly $1000 for an ER visit, even after my private US health insurance mandated a discount).

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.

I soon realized that this 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. And few travel insurance companies allow one to buy additional coverage after one has left their place of residency.

So I had to look for a new solution.

Annual Travel Insurance

I next purchased an annual travel insurance policy to cover all trips I might take during a year. I liked that I would not have to remember to buy travel insurance for each trip.

But I soon discovered that most annual plans (including the plan I purchased) had trip length limits. These trip length limits are noted in the small print, are not easy to find, and were not pointed out to me—even though I asked about it before I purchased the plan.

So 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

Then I found travel insurance that covered multiple destinations, in the USA and internationally, for short- and long-term travel, with the flexible purchase options I needed. So I’ve used World Nomads for years. Below I detail these travel insurance needs of mine…

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 need to visit multiple destinations without having to return home between destinations

• I need to purchase/repurchase while I’m traveling (so I can roam free/travel indefinitely)

• I need USA and international coverage (more than 100 miles from home)

• I need to travel short- and long-term (I tend to buy 1-3 months at a time, or up to 180 days)

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

• I want emergency evacuation (at least $300,000)

• since insurance coverage can change anytime, I always read the small print

How World Nomads Has Worked for Me

While traveling out of state, I had to go to a mountain hospital urgent care clinic after hours.

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

Emergency room bills in the USA would frighten anyone. And multiple billings were generated—with one bill arriving a year later.

The hospital and its urgent care clinic always billed my private US state health insurance first, but my private insurance wouldn’t cover everything because this happened out of state.

So I gathered the hospital statements, my private US health insurance responses, and the receipts for what I’d paid out of pocket, telling World Nomads that I still wasn’t sure I’d been fully billed.

I waited patiently during both billing reimbursement processes, which took a long time (which I find typical for insurance, so I choose patience in these situations).

World Nomads covered everything my private USA state health insurance would not. That made me feel grateful.

What about travel insurance with different—or more—benefits?

Some need travel insurance with different or more benefits. The other two travel insurance products I’ve found that meet most of my travel insurance flexibility needs are…

• Genki (Explorer)

  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 (Nomad Insurance)

  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.

Affordable Air Ambulance Insurance

I should note that I’ve also purchased affordable annual air ambulance insurance to cover potential emergencies while traveling (and living) in more remote areas.

When I spent quite a bit of time between my home state and AK, I had an annual Airlift NW membership.

When I’ve traveled or lived more remotely in the USA states of WA, ID, MT, and/or OR, I’ve purchased an annual Life Flight membership.

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

Of course, if my travel insurance covers this expense, I don’t need this annual membership, too.

Saving Money When Buying Travel Insurance

Before buying travel insurance, though, I verify the following so I don’t pay twice for the same coverage…

• what my private US state health insurance will/will not cover while I’m traveling

• what my credit card benefits cover while I’m traveling (small print is essential to read)

• when I have renter’s insurance, what it will/will not cover while I’m traveling

• when I had homeowner’s insurance, what it would cover while traveling

How About International (Worldwide) Health Insurance?

I’ve also wanted international (worldwide) health insurance to cover regular healthcare needs (not just travel emergencies) while traveling full-time out of the country. In the past, these policies were too expensive for my age, plus a non-US residency address always seemed required. But I am hoping for that option in the future. Right now, it appears the following insurance might be worth investigating for full-time worldwide health insurance needs … so I’ll check them out when I’m ready for that…

• Genki Native (for those over 55, Genki told me 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 (Nomad Health)

  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.