When most people think about travel insurance, they think about one thing:

What if I get sick and can’t go?

But sometimes the biggest travel disasters happen when you’re still very much planning to take the trip.

A canceled flight. A missed connection. Weather. Delays. One unexpected problem that suddenly throws every carefully planned piece of your itinerary into question.

That’s exactly what happened to my family before our trip to Alaska in 2022 - and it’s the experience that completely changed the way I think about travel insurance.

The Night Our Alaska Trip Almost Fell Apart

My husband works at the airport, and at the time, he was working nights.

Our flight was scheduled to leave around 6:30 AM.

At about 1:30 in the morning, after getting my son to bed, finishing the packing, going over my checklist one more time and finally feeling like everything was ready, I laid down to go to sleep.

Literally as I was falling asleep, I got a text from my husband:

“Umm… our flight is cancelled.”

I laughed.

He knows how crazy I get preparing for a trip, so I was positive he was messing with me.

Then came:

“No, it’s actually cancelled.”

I still didn’t believe him.

So I checked my email.

And there it was.

Our flight had been canceled, and because of limited availability, the airline wasn’t able to automatically rebook us within the next couple of days.

UMMM, WHAT?!

I immediately went into panic mode.

My mom came over for moral support while I spent hours on the phone with airlines trying to figure out how we were getting to Alaska.

One thing was certain:

I was not canceling this trip.

Plan B: Get to Alaska Somehow

Eventually, I found a last-minute flight departing from Baltimore the following day.

Baltimore. Four hours away.

Since our return flights were still coming back into Pittsburgh, we didn’t want to leave our own car in another state.

So we rented a car, drove to Baltimore and flew out from there.

Not exactly the relaxing start to vacation I had planned.

But getting ourselves to Alaska was only part of the problem.

This wasn’t a simple trip where we were checking into one hotel for a week.

I had planned a completely custom 10-day itinerary, and we were moving around throughout the trip.

Missing that first day had the potential to throw off everything that came after it.

And I was not about to miss a stop on my carefully planned Alaska itinerary if I could help it.

So I started moving everything.

Accommodations. Tours. Rental cars. Reservations.

I called suppliers, explained the situation, asked for flexibility, shifted dates and rebuilt our itinerary around our new arrival.

Some things could be changed easily.

Some couldn’t.

And by the time everything was said and done, we had spent more than $3,500 out of pocket trying to salvage the trip.

Why Was I Willing to Spend That Much?

Because the entire time, one thought kept running through the back of my mind:

We have travel insurance.

Followed closely by: I really hope they cover this.

Our policy was through Travel Insured.

After the trip, I submitted the claim, provided the required documentation and waited to see what would happen.

And in our specific situation, Travel Insured reimbursed every dollar of those covered expenses. More than $3,500.

That experience is a huge part of why I feel so comfortable discussing Travel Insured with my clients today.

Travel Insured is Diserella Travel’s preferred third-party travel insurance provider, and it’s the company I provide quotes through for clients looking for coverage outside of an option offered directly through their vacation supplier.

But even before I worked for Diserella Travel, I had already used Travel Insured personally.

I purchased a plan. I needed it. I worked with their Customer Service team to file my claim.

And I experienced firsthand what it feels like to be staring at thousands of dollars in unexpected travel expenses and hoping the protection you purchased actually helps.

So when I talk to my clients about travel insurance, I’m not just repeating something I’ve read in a brochure. I’ve lived it.

Travel Insurance Isn’t Just About Getting Sick Before a Trip

That is probably the biggest misconception I hear.

People often think of travel insurance strictly as:

“What if I get sick and have to cancel?”

But travel can go sideways in a lot of different ways.

Flights get canceled. Delays derail plans. Weather does its thing. Connections get missed. Plans fall apart... fast.

And sometimes you don’t want to cancel the trip at all.

Sometimes you just need to figure out how to save it.

That was us. Our trip wasn’t over. We just needed a completely new way to get there.

And We Took the Trip

After all of that chaos, we made it to Alaska. We shifted the itinerary. We kept almost everything I had planned. And the trip turned out to be incredible.

You can read more about that adventure in my Alaska blog - because yes, after everything that happened, we eventually made it. And looking back, the part I remember most isn’t sitting on hold with an airline at 2 AM.

It’s Alaska. The scenery. The experiences. The memories. The chaos was temporary.

But without travel insurance, that temporary chaos could have left us with a very permanent $3,500+ reminder of everything that went wrong.

That trip completely changed the way I view travel insurance.

I don’t look at it as something you buy because you expect your vacation to go badly.

I look at it as something you purchase because no matter how carefully you plan, there will always be things you simply cannot control.

And sometimes travel insurance isn’t about helping you cancel the trip.

Sometimes it’s about helping you take it anyway.

Life is short. Book the trip. And purchase the insurance.

DISCLAIMER:

Travel insurance policies vary widely and may include different benefits, limits, exclusions, eligibility requirements and documentation requirements.

Purchasing travel insurance does not guarantee that a claim will be approved or that a particular expense will be reimbursed.

My family’s experience described above reflects our specific circumstances, our policy and our claim at that time. It should not be interpreted as a guarantee that another traveler, policy or claim would receive the same result.

Travelers should review the applicable plan documents carefully and contact the insurance provider directly with specific questions regarding coverage, benefits, exclusions or claim eligibility.