Why Travel Insurance Matters More Than You Think (Especially When Traveling Outside the Country)

Travel insurance often feels like an optional add-on, but it’s one of the most important investments you can make when traveling outside the country.

At the end of a beautiful week hiking through the rolling hills of Italy’s Chianti region, I wasn’t thinking about hospitals, surgeries, or $16,000 flights. I was thinking about pasta.

I was dressed for dinner, heading out of the hotel with my husband, when I missed a step. Everything changed—I heard cracks in both ankles, one after the other, and found myself unable to stand. It wasn’t on the trail that I hurt myself, but on a cobblestone sidewalk just steps from our hotel.

What happened next could have easily turned into a logistical and financial nightmare. But because I had purchased travel insurance ahead of time, the entire experience was far less overwhelming than it might have been.

This isn’t a story about fear—it’s a story about preparation. Travel insurance often feels like just another line item on an already pricey itinerary, something you assume you’ll never actually need.

I used to feel the same way—even though I still bought it, just in case. But after what happened on my most recent trip abroad, I can say with certainty: I will never travel internationally without it again. Here’s why.

A Sudden Injury Abroad

My husband and I were nearing the end of a multi-day hiking trip in Tuscany, a region we chose for its scenic vineyards and charming hill towns. We’ve done several active trips like this before, including the Tour du Mont Blanc and Iceland’s Laugavegur Trail.

Knowing the physical risks, I always purchase a travel insurance policy through World Nomads that includes medical coverage, travel interruption, and lost or delayed baggage. My biggest fear has always been injuring myself somewhere remote on the trail.

Ironically, the injury didn’t happen while hiking. It happened on a cobblestone sidewalk, when I simply stepped wrong. In an instant, our vacation plans turned into a medical emergency.

The hotel quickly called a taxi to take me to the emergency room in Siena, where I was treated at a public hospital. I contacted World Nomads’ emergency medical provider, Generali Global Assistance, while sitting in the ER.

They took the hospital information, initiated my claim, and immediately began coordinating care. Thanks to Italy’s public healthcare system, there was no charge for the ER visit—but everything else, from taxis to wheelchairs, was now a matter of urgent logistics and cost.

What My Policy Covered

Fortunately, what could have been a chaotic scramble became a well-organized response. Here’s what the travel insurance helped cover:

• Emergency transportation. This included my initial taxi to the hospital, plus later transport from the ER back to our hotel and eventually to the airport.
• Medical equipment. My husband was able to purchase a wheelchair from a local medical supply store and prescriptions from a nearby pharmacy—expenses eligible for reimbursement.
• Flight changes. Due to medical restrictions, I couldn’t fly home in a standard seat. Generali arranged two lie-flat business class tickets for my husband and me—flights that would have cost $16,000 out of pocket.
• Airport assistance. The insurer coordinated wheelchair support at the airport, ensured my husband was listed as my medical assistant, and arranged for us to be boarded separately from other passengers for safety.
• Trip interruption. Since we missed the last couple of days of our itinerary, meals, lodging, and unused prepaid activities became reimbursable under the policy.
• Delays and disruptions. On top of the medical situation, we also experienced baggage delays at the start of the trip and flight delays on the way home—again, all eligible for claims under the travel insurance policy.

I filed the initial claim from my phone while lying in a hospital bed. From that point forward, Generali handled most of the logistics.

I didn’t have to chase down flights, haggle with airport staff, or stress about how to get home. When you’re in pain and disoriented in a foreign country, that kind of support is priceless.

What Travel Insurance Typically Covers

Coverage varies by provider and policy, but here are some of the common protections comprehensive travel insurance plans include:

• Emergency medical and dental care. If you’re injured or become seriously ill while traveling abroad, travel insurance can cover the cost of hospital visits, doctor fees, prescription medications, and even emergency medical evacuation in some cases. This feature alone can make the policy worthwhile, as medical evacuations can cost anywhere from $20,000 to over $200,000, depending on your location and the level of care you need.
• Trip interruption and cancellation. This reimburses you for unused, prepaid trip expenses if your travel is cut short due to illness, injury, or another covered reason.
• Baggage loss or delay. If your luggage goes missing or arrives late, insurance can reimburse you for essentials like clothing and toiletries.
• Travel delay or missed connections. If your flight is delayed or canceled, you may be eligible for reimbursement of meals, hotels, and alternative transportation.
• 24/7 travel assistance. Most policies offer access to multilingual support lines to help you coordinate care, replace lost passports, and find local services.
• Accidental death or dismemberment. This sobering benefit provides a financial payout to your beneficiary if a worst-case scenario occurs.

Despite offering extensive coverage, travel insurance is often surprisingly affordable—around 4% to 6% of your total trip cost, on average. In my case, the premium was about $200, which is less than we might spend on a dinner for two. This coverage ended up shielding us from tens of thousands of dollars in unexpected expenses.

What Travel Insurance Doesn’t Cover

Like any form of insurance, travel coverage has its limitations. Once I returned to the U.S., my policy no longer applied, meaning my surgery, physical therapy, and ongoing recovery are now handled through my domestic health insurance, which still comes with its own out-of-pocket costs.

I was also fortunate that our upcoming summer trips were fully refundable. Otherwise, I would’ve been on the hook for those cancellations, since I hadn’t yet purchased travel insurance for them. After this experience, I won’t wait to secure coverage in the future.

In general, travel insurance doesn’t cover every possible scenario. For instance, non-emergency dental care, pregnancy-related treatment, and injuries from high-risk activities are typically excluded. While that can be frustrating if any of these apply to you, the core benefits can still save you thousands in unexpected expenses.

Lessons Learned: The True Value of Planning

I’ve always believed in the importance of travel insurance—especially for international or active trips—but this experience drove the point home in a way I never expected. Life is unpredictable, and the truth is, even the most carefully planned adventures can take a sharp turn when you least expect it.

I didn’t hurt myself while hiking through remote vineyards or summiting a mountain. I missed a single step walking out of a hotel on my way to dinner. No amount of planning could have prevented that fall, but having the right policy in place meant we could focus on getting home safely, not scrambling to figure out logistics or cover massive costs.

Although I’m still working through the claims process, the support I’ve received so far has been outstanding. And most importantly, I didn’t have to navigate it all on my own, which made an overwhelming situation much more manageable.

If you’re considering travel insurance, keep in mind you don’t have to go with the same provider I did. There are many reputable travel insurance companies, including Allianz Global Assistance, AIG’s Travel Guard, and Faye.

Each one caters to different needs and travel styles, so take the time to find the policy that best fits your plans. And don’t forget—timing is everything. Travel insurance only protects you if it’s in place before the unexpected occurs.

Simplicity Wealth Management Is Here to Help

I hope my story offers a helpful reminder to fellow travelers—and a nudge to anyone who’s been on the fence about buying coverage. When possible, I like to use my own experiences to help guide my clients through the financial decisions that matter most.

If you’re looking for a financial partner who can help you prepare for both the expected and the unexpected—whether that means selecting travel insurance, optimizing equity compensation, or planning for the future—Simplicity Wealth Management is here to help. Book a complimentary Simplicity Session today to start planning with confidence.