You’ve planned. You’ve dreamed. You’ve counted the sleeps.

That trip you've been so excited about is finally just around the corner...

And then — bam!

Out of nowhere, life throws you a curveball.

And suddenly, you’re not going anywhere.

💔 Maybe it’s a medical emergency.
💔 Maybe someone you love needs you.
💔 Maybe it’s something you never saw coming.

Whatever it is, the trip you poured your heart (and maybe your savings) into… has to be cancelled.

I know how disappointing, stressful, and even surreal that can feel.

And I also know you might be thinking:

"Raewyn, what are the chances of that actually happening?"

Truth? They’re higher than we think, especially as we get older.

💭 My Story

Over the years, I’ve had to cancel a few smaller trips. Frustrating, yes — but manageable.

But I’ve also had to cancel two of my dream trips. And those ones hit differently.

Bora Bora: The Trip That Had to Wait

Since I was a little girl, I dreamed of visiting Bora Bora.

Crystal-clear lagoons, overwater bungalows, total bliss.

After a particularly grueling consulting project, I finally booked it.

My reward. My celebration.

But just a month before we were set to leave, our sweet Golden Retriever, Annie, was diagnosed with a tumor on her heart.

If you’re a fur mama, you know, there was no question. The trip was off.

Much of it had been prepaid. We were far past the cancellation window.

But more on what happened next… in a minute.

Thailand & Vietnam: A Journey Interrupted by Loss

More recently, I had planned a six-week solo trip through Thailand and Vietnam, something I had been so looking forward to.

But just weeks before I was supposed to leave, my husband suffered a traumatic brain injury from a fall. He broke his neck and passed away shortly after.

I started cancelling everything from the hospital that very night.

No questions. No hesitation. Just heartbreak.

These aren’t easy stories to tell. But they are real. And they’re why I’m writing this blog.

Because sometimes travel doesn’t happen the way we hope.

And as women in midlife, we know: life changes fast. Health, family, circumstances — they can shift in an instant.

So how do we protect our plans, and ourselves, just in case?

✈ Travel Insurance 101 (Real Talk Version)

First, a disclaimer: I’m not a travel insurance expert.

What I share here comes from personal experience and my own comfort level with risk.

Please always consult a professional when choosing a policy.

That said, here are a few types of coverage to know about:

• Trip Cancellation Insurance – For prepaid, non-refundable costs if you cancel for a covered reason (e.g., illness, injury, death in the family).
  
  

• Trip Interruption Insurance – If you have to cut your trip short unexpectedly.
  
  

• Emergency Medical Evacuation & Repatriation – If you need to be transported to a medical facility or home.
  
  

• Accidental Death & Dismemberment (AD&D) – A financial benefit to your family in the event of something tragic.

• Adventure or Sports Coverage – If you're planning activities like diving, skiing, or zip-lining, these usually need extra coverage.
  
  

  

🧐 What to Check on Your Policy

• How much you’ll be reimbursed (often it's partial, not full).
  
  

• The maximum payout amounts per situation.
  
  

• What’s actually covered — and what isn’t.
  
  

If you’re covered for pre-existing conditions.

• If “Cancel for Any Reason” (CFAR) is available — and how much of your trip it would refund.
  
  

• Deadlines for filing a claim.
  
  

• The documentation required.

🏨 Understanding Cancellation Policies

Even if you don’t have insurance, hotels, tour operators, and airlines all have cancellation policies — and they’re not all the same.

Example from a real hotel:

• Cancel more than 22 days out? Full refund.
  
  

• Cancel between 21 and 8 days? 50% refund.
  
  

• Cancel within 7 days? No refund.
  
  

📝 Tip: Always read the cancellation policy carefully.
Sometimes the language is clunky or unclear. Make sure you understand the timeline.

💡 When You Need to Cancel — What Helps

Cancel as soon as you know. It increases your chances of getting something back, and gives others the opportunity to rebook.

Check the refund timing. Some refunds take 24 hours; others can take a month.

Keep currency exchange in mind. If you paid in another currency, the refund may not match the original amount.

💛 The Kindness That Surprised Me

Now, the good news.

When I cancelled Bora Bora, we were long past the refund window.

But when I told the St. Regis about Annie’s diagnosis, they gave me a full refund — no questions asked.

Two years later, we finally made it to Bora Bora — and of course, we stayed at the St. Regis.

They had earned my loyalty forever!

When I cancelled my Thailand–Vietnam trip, I received heartfelt notes from hotels. One airline even sent a personal message.

A fully prepaid hotel in Vietnam — with a strict no-refund policy — offered me a credit if I rebooked within 12 months.

Guess what’s at the top of my 2026 list?

🌿 In Summary: Protecting Your Peace of Mind

The reality is: your travel plans might change.

Your health, your loved ones, your life — it can shift in ways we never expect.

But here’s the thing — you’re not powerless.

You can protect your plans, make informed choices, and navigate changes with grace.

✨ Your budget is yours.
✨ Your risk tolerance is yours.
✨ Your travel journey is yours.

There’s no one-size-fits-all answer here.

Just real stories, honest reflection, and what I hope is helpful advice, from one traveler to another.

💖 A Final Thought

If you ever have to cancel a trip, I want you to know this:

🔆 It doesn’t mean you’ve failed.

🔆 It doesn’t mean the dream is over.

🔆 It just means… not right now.

Kindness goes a long way. Be honest. Be transparent.

Ask the question — even if the policy says "no refunds." You might be surprised.

And remember — the world will still be there when you're ready.

So if your plans have to pause… just know that your next adventure might be even more meaningful when it finally arrives.

You’ve got this. And I’m cheering for you.

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So cheers to wheels up to winging your way on your next travel building lasting memories.