Travel Insurance Because “I’ll Probably Be Fine” Isn’t a Plan


Why Travel Insurance Matters (Especially Traveling Outside the U.S.)

Travel insurance is one of those topics that people either avoid entirely or overcomplicate. After years of traveling, for work, for life, and now mostly for enjoyment - I’ve landed somewhere in the middle.

I want coverage that actually matters. I don’t want to buy protection I don’t need. I’m sharing how I personally think about travel insurance, not as a scare tactic, but as someone who:

  • travels often
  • cruises multiple times a year
  • works in the travel industry
  • and values flexibility and peace of mind

This is not advice you must follow - it’s simply how I’ve chosen to approach it, and why.

For U.S. citizens traveling internationally, including cruises that visit Mexico, the Caribbean, or beyond, travel insurance is highly recommended. Not because everything goes wrong… but because when something does, it can get expensive very quickly.

Two areas matter most:

  1. Medical care outside the U.S.
  2. Emergency transportation or evacuation

Most people don’t realize that:

  • Your U.S. health insurance may not cover you internationally
  • Cruise ships have medical facilities, but serious issues often require transfer to shore
  • Medical evacuation costs can reach tens (or hundreds) of thousands of dollars

That’s the risk I’m actually insuring against, not a missed excursion or a delayed bag.

Why I Carry an Annual Travel Insurance Plan

I now cruise 3 to 4 times a year, and I travel enough that buying trip-by-trip insurance no longer makes sense for me. For the past few years, I’ve carried an annual travel insurance policy with Allianz. My plan is $280 per year. Please reach out with your needs for a quote.

My plan covers:

  • Multiple trips per year
  • Trip cancellation and interruption (within limits)
  • Emergency medical coverage
  • Strong emergency evacuation coverage

For someone like me, an annual plan:

  • Simplifies decision-making
  • Avoids forgetting to add insurance
  • Provides consistent protection across trips

I don’t have to re-evaluate insurance every time I book, it’s already there. If you travel frequently as well as Internationally, I highly recommend a lower cost annual travel insurance plan.

Why I Sometimes Say “No” to Cruise Line Protection

Cruise lines offer their own vacation protection plans, and for some travelers, those plans make sense, especially if:

  • They don’t already have insurance
  • Their trip cost is high
  • They want cruise-line-specific cancellation flexibility

But insurance should be situational, not automatic.

For example, I recently booked a cruise with:

  • A low cruise fare
  • A refundable hotel
  • A low-cost flight
  • Total trip cost under $900

Because I already have annual coverage, adding cruise-line protection would have duplicated benefits I already carry, without adding meaningful value for that trip.

A Note About “Cancel for Any Reason”

This comes up a lot. Some plans advertise flexibility that sounds like “cancel for any reason,” but often:

  • Reimbursement is partial
  • Payment may come back as future credit, not cash
  • There are time-based restrictions

Those features can be helpful but they’re not free, and they’re not always necessary. In my case, I look at:

  • What I could realistically lose
  • Whether I’m comfortable with that risk
  • What coverage I already have in place

Then I decide. I advise my clients to go through the same process.

Why I Didn’t Switch to a Lower Cost “Professional” Plan

As a travel advisor, I qualify for a Travel Professional insurance plan that costs much less than my annual policy. When I noticed that, I paused and compared the coverage.

Here’s the key difference:

Emergency evacuation coverage.

My current annual plan provides significantly higher evacuation coverage than the professional plan. On cruises and international trips, that’s the line I’m not willing to cut.

The lower cost plan is fine for:

  • Domestic travel
  • Short trips
  • Low-risk scenarios

But for cruising, I’m keeping what I have.

Sometimes cheaper is fine. Sometimes it isn’t.

How I Handled Flight Risk Without Buying Extra Insurance

One more real-world example that reinforces my overall approach.

For my flight, I added Frontier’s Disruption Assistance for $10 each way. This covers the most common airline issues like delays or cancellations by:

  • Monitoring my flight automatically
  • Offering rebooking options on the same or next day, even on another airline
  • Providing a refund option if the alternatives don’t work

This doesn’t replace travel insurance, and it’s not meant to. It simply handles flight disruption risk, which is one of the most likely issues travelers actually face today.

I'm set with:

  • My annual travel insurance for medical and evacuation coverage
  • A refundable hotel reservation
  • A low overall trip cost

This made adding cruise line insurance unnecessary for this particular trip. This is what I mean when I say I don’t overbuy insurance. I layer coverage intentionally instead of duplicating it. Each piece does a specific job, and together they cover the risks that matter most.

For low-cost trips especially, this approach keeps things simple, flexible, and cost-effective.

A Note About Global Events and “Acts of War”

We are living in interesting times, and it would be unrealistic to pretend global events never affect travel. While none of us plan trips expecting disruption, it’s worth understanding that certain situations, including acts of war or government action, can fall outside standard coverage or trigger specific policy language.

This is another reason I focus on insurance that prioritizes medical care, evacuation, and the ability to get home safely if plans change unexpectedly. No policy can cover every scenario, but being aware of exclusions, travel advisories, and assistance services helps you make informed decisions rather than reactive ones.

Prepared does not mean worried. It means understanding the landscape and choosing coverage that supports flexibility and safety in a changing world.

The Laptop Lyfe Perspective

Many of us:

  • Travel often
  • Mix personal and professional life
  • Value freedom and flexibility
  • Don’t want to overthink every decision

Insurance shouldn’t add stress - it should quietly support the life you’ve chosen.

For me, that means:

  • Carrying strong annual coverage
  • Skipping unnecessary add-ons
  • Focusing on experiences, not worst-case scenarios

I also want to say this clearly:


When I cruise, I unplug.

I leave my laptop at home.
I don’t buy ship Wi-Fi.


My phone works in port if I need it, and otherwise I enjoy the downtime. That reset is part of why I travel - and why insurance matters. It lets me fully step away.

Final Thoughts

Travel insurance isn’t about fear.
It’s about being intentional.

There is no single “right” policy, only the right fit for how you travel.

If you travel occasionally, you might choose differently than I do.
If you cruise often, your priorities may shift.
If you’re new to travel, you may want more guardrails.

All of that is okay.

Want to Keep the Conversation Going?

I share travel experiences, planning thoughts, and real-world decisions like this inside my Go Wild Locals Facebook group.

If this topic resonated with you, or, if you’re curious about cruising, flexibility, or intentional travel, you’re welcome to join us. No pressure, just conversation, curiosity and shared experience.

👉 Go Wild Locals FB group

Go wild when the timings right - Vicki

✨ Bonus Tip: Before you travel, take two minutes to screenshot your policy benefits and assistance numbers. You will never need them until you really need them, have them handy.

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