A note before I start: my mother-in-law passed away in July. Much of this post was written while she was still with us, when the shape of the summer was disappointment and dread but not yet grief. I’ve come back to finish it because the practical parts still matter — maybe more than they did before. She would have wanted the lessons here to be useful to somebody.
What travel insurance actually covered when we cancelled $50,000 in bucket-list trips
New here? My earlier post on how I think about travel insurance in general is the primer. This one is the case study.
The plan for this summer was two bucket list trips. The Amazon and Machu Picchu for our family, and Iceland for my in-laws. My mother-in-law had lived with metastatic breast cancer for thirty-plus years, most of it quietly in remission, and Iceland was hers. Ours was an Amazon cruise with National Geographic/Lindblad — a 14-room ship, two of the rooms ours — plus Explora in the Sacred Valley and a splurge night at Sanctuary Belmond, the only hotel at the entrance of Machu Picchu.
She was placed on hospice the week before we were supposed to leave. Both trips came off the board within days, along with summer camps, scheduled surgeries, camping trips with friends, and everything in between. My own body responded the way bodies do under sustained stress: my hyperthyroidism came back with a vengeance, I couldn’t stand or walk without being winded from the tachycardia, and the insomnia was the worst part.
And on top of all of it, we were staring at a $50K loss on trips we cancelled 48 hours before we were supposed to board a flight to Lima. I’ve shared too much about our family and my own personal health already, so why not share a few more numbers for context? The Amazon cruise was $34K. The Peruvian extravaganza plus the Iceland trip totaled about $50K. This is not our usual travel budget — the only other trip of this magnitude was our African safari for Great Migration. Fifty thousand dollars, gone in the space of a weekend, on top of everything else.
Cue travel insurance. I have become intimately familiar with travel insurance this summer, and it has been the one bright spot in an otherwise very dark stretch. I didn’t do everything perfectly. I made my fair share of mistakes. But I’m here to walk you through all the things I did right, all the things I did wrong and would change, and all the stop-gaps that ultimately made it so that we broke even despite not having the perfect coverage.
The baseline setup
At baseline, my family has an annual plan with Allianz and a 5-year plan with Medjet for evacuation. The annual plan ranges from $2K coverage to a max of $15K coverage. That’s the total covered across all travelers on the plan, across all trips for the year. My annual plan for 2025-2026 was the $10K plan. This covers all our small weekend trips or trips booked on points where I didn’t feel like there was enough financial incentive to set up a separate trip-specific plan, but it also serves as extra coverage for each trip you do decide to insure.
For our Peru trip, our cruise alone was $34K (yeah, I know). I had the $10K annual plan, so when I set up my trip-specific plan, I set it up for $26K thinking that would fully cover us (flights were on points with some taxes/fees). Then in April, my husband found out he had the flexibility to travel a bit longer. Yours truly never half-asses anything, so I added Explora Sacred Valley (I’ve been itching to experience Explora), a night in Aguas Calientes, and most importantly a night at Sanctuary Belmond. That last one is the only hotel at the entrance to Machu Picchu — it lets you do their early-light experience where you watch the sun rise over the ruins before crowds arrive, and stay later after crowds leave because you don’t have to catch the last bus down. And let’s not discount being a hotel guest and being able to return to your room for the bathroom between routes.
All of my additions added another $10K to the trip, and I didn’t think to revise my travel insurance plan.
Nugget #1: Take your best guess at coverage amount when you book, then revise it later.
The second mistake
My annual plan ran June 2025 to June 2026. In May, I got a notification that it was about to expire and I renewed it. I started the next annual plan on June 13th, the first day of our Peru trip. My thinking was that it would cover the trip from beginning to end.
That was my second mistake. I should have started the plan on the day I paid, not the first day of travel. I cancelled our Peru trip on June 11th and tried to claim against my 2026-2027 plan, but since coverage wasn’t set to take effect until June 13th, the June 11th cancellation happened before my effective date.
Nugget #2: Start your annual plan on the first day you could potentially cancel your trip, not on the first day of your trip.
What Allianz actually covered
All that said, Allianz covered the full $10K on my 2025-2026 plan and the full $26K on my trip-specific plan. What was the process like?
For a covered reason (and the T&Cs are surprisingly generous — read them), there’s a big document lift. For illness of a family member, we had to provide:
- Hospitalization note
- Physician note advising you not to travel
- Each booking confirmation you’re claiming
- Credit card statement showing you paid for each booking (and if you paid for a cruise over 8 payments, you need all 8 statements)
- Cancellation confirmation for each booking
- Terms and conditions for cancellation for each booking. I went one step further and had each agency issue me a letter summarizing what I paid to them and that I was getting zero back per their cancellation policy
- Any partial refunds (port fees, redeposited points, future hotel credits) — you have to disclose those too
- Not required but very helpful: a summary letter for the reviewer, listing the various bookings you’re claiming, the penalty amount for each, and any refunds you’ve already subtracted out. You have a ton of documents to gather and they have a ton to go through, so the clearer you can be on the ask, the better
Once I submitted everything, Allianz took about a week to review and then sent the decision letter: approved for $10K on the 2025-2026 annual plan, approved for $26K on the trip-specific plan, denied on the 2026-2027 plan (because I cancelled two days before it took effect, which is fair). The next day I got an ACH transfer notification for the bank account I provided. Done. Easy peasy.
Where credit cards came in
At that point I was ready to assume we were out about $10K for Peru and another $5K for Iceland, since both were cancelled before my 2026-2027 plan took effect. This is where credit card coverage came in. I’m in the points game, so all my credit cards are high-annual-fee cards and many of them are travel cards with trip cancellation coverage. I sifted through which payments went on which cards, read the T&Cs for each card’s coverage, and started the submission process again.
For credit cards, the document list is similar to what Allianz asked for, plus a statement from Allianz indicating what they covered. You can only claim for payments you made on that specific card, so I ended up filing against three: Amex Business Platinum, Chase Sapphire Reserve, and Chase Ink Business Preferred.
One thing to know: when you submit to Allianz, you tell them you’re requesting $1,234 for hotel A and $2,345 for flight B, etc. When they issue the refund, they don’t break down what their payment covered, and you can’t retrieve a copy of what you submitted. So keep your own records of your submission. Fortunately I had it all in an Excel spreadsheet so I could break it down line by line, but the statement had to come from Allianz. I called their agent and asked if they could issue me a statement indicating they covered $1,234 for hotel A, $2,345 for flight B, and $3K of the $34K cruise, for example, on one plan. I did this for each plan (annual and trip-specific), then submitted those documents to the credit card companies.
The credit cards will only cover what your travel insurance didn’t. Since I hadn’t fully covered the trip with Allianz, I mapped the math and requested the delta from the card issuers. This took a little longer (back-and-forth over documents was about two weeks), but ultimately all three cards paid out: Amex Business Platinum for our Iceland cruise, Chase Sapphire Reserve for Explora, and Chase Ink Business Preferred for some of the cruise payments.
I put about $24K of the cruise on CIBP (travel codes as 3x on that card), but only claimed a portion since Allianz had covered part of it. I requested Chase cover the remaining $10,600. Note that CIBP has a cap of $10K total across all travelers per trip ($5K per traveler, $10K per trip, max $20K over 12 months), so they issued me a check for the maximum $10K. CSR has higher coverage — $10K per traveler, $20K per trip, max $40K per year.
Whether my personal travel would be covered when charged to a business card never came up. To be fair, I’m a travel agent and I was ready to submit statements that this was at least in part a business trip, since all my Explora bookings were through my travel-agent email and liaison. Chase never asked. I don’t think they care whether it was personal or business travel.
Nugget #3: Know each card’s limit if you plan to use your credit card as a stop-gap or as primary coverage. Also: carefully track what has been claimed against travel insurance versus credit card, and don’t try to double-claim anything. It is a punishable crime to mislead insurance companies, so I kept meticulous notes to prove that if Allianz covered something, I wasn’t requesting the same thing from Chase or Amex.
The in-laws’ trip
Finally, the in-laws’ trip. This is the one we lost. Because my mother-in-law had a cancer diagnosis (30+ years, mostly in remission), it counted as a pre-existing condition. We did not request a pre-existing condition waiver because the cancer was in remission and not an issue at the time we booked the trip and the travel insurance. We had her on the same plan as my sister-in-law’s family (eight people total on one plan). Since the hospitalized/ill traveler was on the trip and we didn’t have a waiver, they denied the claim in its entirety.
We fought it. We obtained a letter from her oncologist stating that her cancer was in remission at the time of booking, that she was encouraged to travel, and that the deterioration did not occur until much later. We submitted the reconsideration and asked whether they would at least cover the other seven travelers on the plan. The final answer was no. Without the waiver, the claim stayed denied.
The lesson still stands, and honestly it stands harder now that I’ve watched it play out in real time.
Nugget #4: If there is a serious medical condition in one member of the traveling party, either obtain the pre-existing condition waiver or insure everyone else separately on a different plan.
Cancel for any reason
The other thing we could have done is purchase Cancel For Any Reason (CFAR) insurance. CFAR needs to be set up within two weeks of your initial deposit, and if we’d had it, my mother-in-law’s cancellation would have been covered even without a waiver. CFAR is more expensive and needs to be set up early.
Nugget #5: Consider a Cancel For Any Reason rider for high-risk individuals or high-risk trips. Our family is going to attempt to see the 2027 eclipse in Egypt, and you can be sure I’m setting up CFAR so I can change my mind if I’m not feeling it due to politics, terrorism, or the heat.
Most travel insurance plans are similar, but I have always liked Allianz for myself and for my clients because their CFAR reimburses 80% of cost for uncovered reasons, while Travel Guard covers 50%. That’s a huge difference. Note that for covered reasons (illness, loss of job, natural disaster, etc.), 100% is covered. If you just changed your mind, or a pet got sick, Allianz would cover you for 80%. That is gold.
The nugget I didn’t want to learn
Nugget #6: Never assume that you won’t cancel a trip.
This was a bucket-list trip. I desperately wanted to (and still want to) experience a NatGeo cruise with their world-renowned photographers, be guided around by locals with Explora, and stay at the entrance of Machu Picchu. In a million and one years, I would not have willingly cancelled the trip. But I’m glad I bought the coverage, because in the end I unwillingly had to.
You may be set on going, but sometimes life has other plans.
What I’d tell you if you were sitting across from me
Could I have paid for less coverage because most of my trip was on credit cards with trip cancellation? Yes. If I hadn’t had an external plan, the cards would have covered me up to $10K per trip on CIBP, $20K per trip on CSR, and $10K per trip on ABP. I could have covered less with Allianz. But it’s a pain to submit all the documents to each card and to track which card each payment went on. Credit cards also offer less in medical coverage, baggage delay, flight delay, and everything else.
So yes, you could do it — read all the T&Cs, make your charts to see how much you put on which card and how much that card will cover. But I would rather cover my trips with dedicated travel insurance and use the credit cards as backup for the times I under-insured something.
Nugget #7: Insurance is worth it, and it’s better to over-insure than under-insure.
I have recovered close to $50K this summer. Which means for the rest of my life I will never feel that I overpaid for travel insurance, because when the unimaginable happens, you will be so glad that at least you are financially whole while you are navigating everything else. If you think there’s a chance you would ever, once in your lifetime, be as unlucky as I was this summer, then travel insurance is a bargain.
I had expected to spend this summer sharing photos of sunrise at Machu Picchu, llamas, and pink dolphins in the Amazon. Instead I spent it at home with my mother-in-law, and afterward, reading terms and conditions. Not the summer I envisioned. But if what I learned here saves even one of you from losing $50K on top of losing someone you love, then the writing was worth doing.