Nobody thinks they'll spend their holiday filing a police report. I didn't either — until I was sitting in a dimly lit station in Punta Cana at midnight, trying to explain in broken Spanish that someone had broken into our Airbnb while we were at dinner.
It was 2023. I was in the Dominican Republic with 2 friends, 4 days into what was supposed to be a laid-back ten days along the coast. I had my travel insurance confirmation in my email, my eSIM for international travel already active so I'd had data from the moment we touched down in Santo Domingo, our Airbnb booked months in advance with amazing reviews.
I was, by every measure I understood at the time, prepared.
We came back from a restaurant in Bávaro to find the door unlocked — not forced, which was somehow worse. Someone had a key, or had been given access, or had found a way in that left no obvious trace.
My friend passport was gone. A laptop. Cash we'd left in a drawer. And the kind of violated, helpless feeling that doesn't leave you quickly, especially when you're thousands of miles from home in a country where you don't speak the language and don't know who to call.
This post is everything I learned from that trip — about what travel insurance actually covers, what it quietly doesn't, and what I wish I'd known before we ever boarded that flight.
The Uncomfortable Truth About Travel Insurance
Hawa Mahal In Jaipur, India
Let me say something the comparison websites won't put on their homepage: travel insurance is designed, in significant part, to protect the insurer. The policy is written by lawyers. The exclusions are numerous and deliberately worded. And they often only become clear when you're sitting in a foreign hospital trying to decipher a document with clauses that reference other clauses.
I know because I've done exactly that. Twice.
Here's what most standard travel insurance policies actually cover well:
- Trip cancellations due to illness before departure
- Lost or delayed luggage (usually up to a frustratingly low cap)
- Basic emergency medical treatment
- Repatriation if you're critically ill
Here's what they're often surprisingly bad at:
- Injuries caused by a third party's negligence — i.e., someone else's fault
- Ongoing physiotherapy and rehabilitation costs after the initial hospitalisation
- Lost income if you can't work for weeks or months after an incident
- Non-medical expenses like damaged equipment, emergency accommodation changes, or legal fees
- Incidents where alcohol was involved, even incidentally
- Pre-existing conditions, sometimes even minor or well-managed ones
Third-Party Negligence – Why Your Insurer Won't Bring It Up
If you slip on a wet floor at a hotel in Bali, trip on a broken step at a trattoria in Naples, or fall because of dangerously poor lighting in a guesthouse corridor in Chiang Mai — your travel insurance will likely cover the ambulance and the emergency room. But it probably won't help you recover the full picture of what that incident actually cost you.
Your insurance covers your risk. It doesn't hold anyone else accountable for their negligence.
An injury on someone else's property — a hotel, a resort, a restaurant, an Airbnb — may entitle you to compensation from that property's own public liability insurance. Most travellers have absolutely no idea this option exists. And insurance companies have zero financial incentive to point you toward it.
This is the part that made me genuinely angry when I finally understood it. My friend's fall in Lisbon wasn't her fault. There was a documented hazard the hotel knew about. And yet she walked away — limped away — with an £800 payout and a voucher, when she likely had a legitimate legal claim against the property itself.
The Airbnb Break-In: What Actually Happened
Airbnb break in Dominican Republic
We'd chosen the place carefully. 4.9 stars, 200-plus reviews, a private villa in a residential area just outside Bávaro. The kind of listing where every photo looks like a travel magazine and every review mentions how safe and welcoming the neighbourhood felt.
We were out for maybe 3 hours. A seafood dinner at a restaurant in town, one drink after, back by 10pm. Not a late night. Not reckless.
The door was unlocked when we got back. We assumed one of us had forgotten to lock it properly. Then Jess went to her room and came straight back out with a look on her face I won't forget quickly.
Nothing was visibly forced. No broken lock, no smashed window. Which meant someone had access — a copied key, a spare that hadn't been accounted for, something the host either didn't know about or didn't disclose. We never found out which.
We called Airbnb from the property. They were sympathetic, opened a case, and eventually refunded the cost of our stay.
Our travel insurance covered some of the stolen items — up to the per-item limits in the policy, which were lower than we'd noticed when we bought it. Cash wasn't covered at all. The emergency passport replacement costs were partially reimbursed after a lengthy claims process that took six weeks and required documentation we'd been too stressed to gather properly in the moment.
Airbnb offered us a voucher for a future stay.
I'm still not over that one either, if I'm honest.
The Skiing Accident That Grounded Me For A Year
2 years ago, I had my own insurance lesson — and this one I can't blame on anyone else.
I was skiing in Hokkaido — Japan's famous ski resort, the one that gets the legendary powder snow that skiers travel across the world for. I'd been there 3 days and was feeling confident. Too confident, as it turned out.
I took a slope that was slightly beyond what I should have been attempting at that point in the trip — not off-piste, just a step up from where I'd been skiing comfortably. My right knee twisted sideways on a landing. Fast, wrong angle, that horrible sensation of something moving in a direction it absolutely should not move.
I knew immediately it was bad. I skied — very slowly, very carefully — back to the base and sat down, and within an hour my knee had swollen to the point where my ski boot felt impossible to get off.
The clinic there treated me, gave me anti-inflammatories, and recommended I see a specialist when I returned home. My travel insurance covered that initial treatment without issue. That part worked exactly as it should.
What came after is where the story gets complicated.
Back in the UK, the MRI confirmed what I'd half-known since I felt my knee twist: a torn ACL and a meniscus tear.
Surgery was recommended. Not optional surgery — the kind where, if you skip it, you're looking at long-term joint damage and a significantly shortened travelling life.
I had the surgery. Then came 8 months of physiotherapy. Then another 4 months of what my physio called “return to activity” work before I was cleared to do anything resembling real exercise or travel that involved more than walking on flat ground. A full year off travel. As a digital nomad, that's not just a physical loss — it's an identity one.
Here's where my insurance situation turned sour.
My policy covered the initial overseas treatment there. It did not cover my UK rehabilitation — because the surgery and physiotherapy happened on home soil, outside the policy's geographical scope. It did not cover my lost income for the months I couldn't work properly. And when I pushed back on the rehabilitation point, the insurer noted that my policy had a skiing exclusion for slopes “above intermediate grade” — a clause I had genuinely not noticed when I bought it, buried in the activities section on page 11.
The slope I was on was technically graded above intermediate.
I was, in the policy's language, in breach.
I paid for eight months of physiotherapy out of my own pocket. I paid for the follow-up MRI scans that tracked the recovery. I paid for the specialist consultations. I had bought believing my travel insurance would protect me, yet it contributed nothing toward.
I now travel with a specialist annual policy that explicitly names skiing, hiking, and every other activity I actually do. It costs more. It's worth every penny.
Steps To Take After A Fall
Most travel content gets to this part and says “contact your insurer.” That's not enough.
If the property was negligent, you have real options — but only if you do the right things in the first few minutes. Here's what I wish I'd known:
1. Photograph Everything Before You Move
Before anyone helps you up, cleans the spill, or puts out a warning cone — get your phone out. Wide shot first, then close-ups. Put your hand or shoe in frame for scale. Those first 5 minutes produce the most important photos you'll take.
If other guests saw what happened, ask for their names and contact info. People are almost always willing to help in that moment.
I did none of this. I would do all of it now.
2. Report It formally Before You Leave
Don't just mention it to whoever's behind the front desk. Ask for the duty manager. Ask for a written incident report with a reference number. If they stall or refuse, send an email to the hotel's official address from your phone before you walk out — what happened, exactly where, exactly when. That timestamp is very hard to dispute later.
3. Get Checked Out
Adrenaline is a good liar. A torn rotator cuff feels like a sore shoulder for hours. A fracture can feel like bad bruising.
Go to a clinic. Get a written report. And be specific with the doctor about what happened — “patient fell on unmarked wet floor in hotel corridor” is useful. “Patient presented with wrist pain” is not.
4. Call Your Insurer
Helsinki, Finland
Report it to activate your coverage. But while you have them on the phone, ask directly: does my policy cover injuries caused by someone else's negligence? Will you help me pursue a claim against the property? Standard policies usually say no to that second question. Some premium annual plans or high-tier credit card coverage include legal helpline access. Find out before you assume.
5. Know That The Property May Owe You More Than An Apology
Hotels and commercial properties carry public liability insurance for exactly this reason.
If a hazard caused your injury — one they knew about or should have caught — you may be entitled to compensation for medical bills, lost income, and health care costs. What that looks like depends on the country and your nationality, which is why it's worth a conversation with a lawyer.
6. Keep Every Receipt
Every taxi to a clinic. Every prescription. Every physio session. Every email to or from the hotel. You won't know in the first 48 hours what you'll need. Keep all of it anyway.
7. Talk To A Lawyer
If the injury meant surgery, time off work, or ongoing treatment — make one call to a personal injury lawyer when you're back. Most offer free initial consultations. Even a single conversation tells you whether you have a viable claim and who it's against.
What To Actually Look For In A Better Policy
High medical coverage limits — especially if you're visiting the US, where a single hospitalisation can exceed what most standard policies cover. Unlimited medical cover is worth the premium.
Explicit medical evacuation cover — if you're trekking in Nepal or diving in Raja Ampat, Indonesia, evacuation alone can cost tens of thousands of dollars.
24/7 assistance with real humans — not a portal or chatbot. A person who can make calls on your behalf in a language you don't speak.
Legal assistance provisions — some premium policies include access to legal advice for third-party claims. Worth having.
Cancellation for any reason (CFAR) — costs more, but functions like the genuine safety net most travellers imagine they're already buying.
Insurance is not a scam. It genuinely helps millions of people and I'm not suggesting you travel without it.
But it is a commercial product with terms designed to limit payout exposure. It has exclusions not prominently featured on comparison sites. And it often stops well short of recovering everything you're owed when the fault lies with a property rather than with bad luck.
The travellers who come out best when things go wrong understood their coverage before they needed it, documented incidents properly in the first chaotic minutes, and knew that an injury on someone else's property might give them legal avenues their insurer has no interest in mentioning.
Travel is still worth it. Enormously, obviously worth it.
Just go with your eyes open.
If this was useful, save it. Send it to someone who travels. The best time to read this is long before you need it.
