How I Chose the Right Travel Insurance Policy Before My Trip

I’d better think about beaches, sightseeing, and good food when my tickets are booked and my suitcase is almost filled.

Instead, I was thinking about all the “what if…” situations. You know the ones. I decided to approach choosing travel insurance seriously.

Why I Started Thinking About Travel Insurance

My BFF returned from Italy with a USD 1,296 bill after a short visit to a local clinic. The reason? A stomach bug and no travel insurance.

“For that money, I could’ve stayed by the sea for another week.”

I thought: okay, this time, I’m doing everything the right way.

How I Defined The Type Of Trip I Was Taking

I was flying for 12 days, planning to rent a car, and even do 1 day of surfing. The type of trip directly affects which travel insurance is right for me. Lying by the pool is one thing, and getting on a surfboard is something different.

How I Compare Different Travel Insurance Policies

I opened about a dozen tabs and quickly realised that I needed to take things step by step, otherwise I’d go crazy.

1. Single-Trip vs Annual Travel Insurance

Annual insurance is my go-to since I travel several times a year. A single-trip policy costs around USD 18–27 while an annual one costs USD 130.

2. Basic vs Comprehensive Coverage

Basic looks great at first, only USD 19. The medical limit is just USD 10,800, though, and that makes me a bit uneasy. Comprehensive for USD 35 covers up to USD 108,000, and the price difference isn’t that big.

3. Medical-Only Coverage vs Full Trip Protection

I thought about taking only medical coverage. Then I remembered when my flight was cancelled, and I lost USD 97 for a hotel night, so I went with full trip protection.

Why The Cheapest Policy Isn’t Always The Best Choice

The cheapest travel insurance looks tempting, but I would never take it. Some of the cheapest travel policies don’t cover flight delays, have a high deductible, and have low medical coverage limits. I didn’t want to save a few dollars now and stress later during the trip.

The Coverage I Pay The Most Attention To

I didn’t read everything line by line. I just paid attention to the things that could actually happen to me.

1. Emergency Medical Expenses

The minimum I’m comfortable with is USD 54,000. Anything below that didn’t really give me much confidence.

Doctors and hospitals abroad are expensive, and that’s no secret, so I’d rather not take the risk. I’d rather pay a little more for insurance now than end up with a very unpleasant bill later.

2. Hospitalisation And Medical Evacuation

“Medical evacuation” sounds good until you see the price: USD 5,400–32,400. No thanks.

That’s why I wanted my insurance to cover those costs in full. It’s one of those things you hope you’ll never actually need.

3. Trip Cancellation And Trip Interruption

Nobody books a trip thinking they’ll have to cancel it, but life sometimes has other plans. If something serious happens and I can’t travel, it’s nice to know I can get some of my money back.

At least my flights and hotel bookings won’t be laughing at me from the cancellation email. I picked a policy that refunds up to USD 1,620 if something legitimate goes wrong and I can’t travel.

4. Lost, Stolen, Or Delayed Baggage

My suitcase and I have a complicated relationship. I made sure I’m covered up to USD 1,080. If it’s delayed more than 6 hours, at least I get something back — not perfect, but fair.

5. Flight Delays And Missed Connections

Flight delays happen more often than I’d like. If my flight is more than 4 hours late, I get USD 108.

It won’t make me rich, but dinner, coffee, and less rage at the airport? I’ll take it. At least waiting around for boarding feels a little less frustrating.

6. 24/7 Travel Assistance

I actually tested the hotline before buying (yes, I’m that person). They picked up in about 30 seconds — no robots, endless menus, or being passed from 1 department to another.

If I ever need to call because of a real problem, it’s nice to know there’ll be an actual person on the other end of the line instead of a recorded message telling me how important my call is. I liked that a lot.

What I Learned From Reading The Exclusions

I wasn’t exactly excited to open the exclusions section, but that’s actually where I found some of the most useful details. After a minute of reading, I realised that a few things worked differently than I’d expected — and I’m really glad I learned that before my trip instead of during it.

1. Pre-Existing Medical Conditions: If you already have a chronic illness or an old health issue, you need to declare it straight away. Otherwise, you go for help, and they tell you: “This was already there, we don’t pay.”
2. Sports And Adventure Activity Limits: Standard insurance doesn’t cover injuries from active sports. So surfing, even just once, isn’t automatically included and has to be added separately.
3. Alcohol, Reckless Behaviour, And Claim Refusals: If something happens while you’re under the influence of alcohol or acting carelessly, the insurer can refuse to pay.
4. Unattended Belongings And Valuables: You leave your phone or bag unattended, and it gets stolen? It’s not covered — that’s your own negligence, not an “insured event.”
5. Cancellation Reasons That Were Not Covered: If you simply change your mind, change your plans, or “don’t feel like going,” insurance won’t cover it. It only works for serious reasons that can be proven with documents.

The Mistakes I Almost Made Before Buying

I was very close to making the same mistakes that a lot of travellers make. When you start looking at dozens of insurance offers, they all seem pretty similar. Once I spent a little more time comparing the details, though, I realised that a small mistake before the trip could turn into a very expensive problem later.

1. Looking Only At The Price

When I started comparing the details, it turned out that a USD 11–16 difference sometimes means the difference between USD 10,800 and USD 108,000 in coverage.

It creates a funny situation: a person is willing to risk tens of thousands of dollars just to save money on a coffee and a sandwich at the airport. After that, the cheapest policies stopped looking so attractive to me.

2. Ignoring Deductibles And Coverage Limits

I almost overlooked this part at first. Then I imagined a situation where I need to see a doctor because of a cold or an injury, and I have to pay the first USD 54–108 myself, and the same thing happens every time I make a claim.

That’s exactly why I chose a policy with no deductible.

3. Forgetting To Check The Full Trip Dates

A classic mistake. Many people buy travel insurance only for the days of their holiday and forget about the travel days.

I almost did the same thing, but then I realised that a trip doesn’t start when you arrive at the hotel — it starts the moment you leave for the airport. If your flight gets rescheduled and you’re delayed, your insurance should still be valid.

4. Not Matching The Policy To My Activities

Not all activities are included in standard coverage. The same goes for mountain hiking, diving, skiing, and even some types of cycling. So now I make a list of what I plan to do during my holiday first, and only then check whether the insurance covers it.

5. Skipping The Fine Print

Boring, but necessary. That’s often where the most interesting details are hidden. Payout conditions, exclusions, limitations, and special rules for baggage or medical claims are usually written in the fine print.

How I Finally Chose My Travel Insurance Policy

After all the comparisons and doubts, the decision turned out to be much easier than I’d expected. Once you ignore the nice marketing promises and focus only on what really matters, the good options quickly rise to the top.

I made a short list of priorities for myself. Medical coverage was at the top.

Next came protection for the entire trip, not just medical expenses. I also paid attention to clear policy terms and reviews from real customers.

If I had more questions than answers, I simply moved on to the next option.

A hospital visit abroad probably isn’t something anyone puts on their holiday checklist. The reality is that medical expenses can turn into the biggest surprise of a trip.

A doctor’s visit, a few tests, some medication, or a couple of days in hospital end up costing more than the holiday itself.

Read: The Accident That Changed Everything

I didn’t spend much time reading the polished reviews on company websites. I looked for stories from people who’d needed help while travelling.

If they said the support team helped them find a clinic, explained what to do next, and resolved the claim, that was a big plus for me. Those were the reviews that gave me the most confidence before buying a policy.

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My travel insurance cost me USD 37. For that money, I didn’t just buy a policy — I bought peace of mind and solid, active coverage.

If you’re still wondering whether you really need insurance, just imagine the worst-case scenario and calculate how much it would cost without it.