I recently updated my own travel insurance and it sent me down a rabbit hole of fine print, hidden limits and cover that sounds great until you realise it only applies if Mercury is in retrograde and you swear not to lose your luggage. So I figured, if I’m doing the admin, I may as well turn it into something useful for others.
Travel insurance isn’t glamorous but it is the thing that saves your trip, your sanity and your bank account when life gets messy. Whether you’re hopping around Europe for weekend breaks or planning a year of adventures, choosing the right policy is one of the smartest bits of prep you can do.
Let’s break it all down in a way that’s simple and helpful.
This guide digs into travel insurance pitfalls you need to watch out for, how to compare policies and how newer nomad-style insurance works if you don’t fancy living by the traditional “pack, fly, return” script.
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Just so you know: This post includes affiliate links. If you decide to buy a policy through one of them, I may earn a small commission, which helps support the blog and costs you nothing extra. I’m not here to sell insurance or tell you what to buy. This is purely a share of my own experience researching, comparing and updating my travel insurance, plus what I’ve learned from using different options while travelling.
What Is Travel Insurance?
Travel insurance is your safety net when travelling or simply planning a trip. It’s there to protect you against travel catastrophes: lost or stolen or lost baggage, cancelled flights, travel delays, stolen gadgets, stolen passports, missed connections, illness abroad, or injuries.
But the key is this: not all policies are equal. Old Ryan would have just hit up a travel insurance comparison website, sorted lowest price to highest and cracked on. But, some travel insurance policies are decent safety nets. Others are like trying to stop bullets with a blanket. Knowing exactly what’s covered (and what’s not) before you click “buy” matters more than the price tag.
Why Travel Insurance is Important
- Healthcare abroad can cause bills that make your heart skip – sometimes more than the holiday cost itself.
- Airlines lose baggage and don’t really care once you walk away. I have been there before and have the receipts to prove it. Sri Lanka 2014 and France 2022 will go down in history!
- Flights get cancelled. Weather happens. Stuff gets stolen. And things go wrong when you least expect them.
- If you travel with gadgets – phones, cameras, laptops – you’re basically shouting “steal me.”
- A decent travel insurance policy can save you stress, money and a ruined trip.
Good cover doesn’t just give you peace of mind. It can also prevent a small crisis from turning into a bigger one.
How to Compare Travel Insurance Policies
When you compare policies, focus on what they do, not just how cheap they are. Ask:
- What’s the medical cover limit? Would this cover you should something go wrong where you are planning to travel?
- Does it include emergency medical treatment, hospital stays, repatriation, ambulances?
- What about baggage, valuables, and gadgets? Are there set limits or exclusions?
- Are delays and cancellations covered? How generous are those clauses?
- What’s the excess or deductible? A cheap policy with a high excess might cost you more when you claim.
- If you do sports/adventure activities – are these covered? Or do you need an add-on?
- Are pre-existing conditions excluded? What about routine care, ongoing treatment, or chronic conditions?
- Going on a cruise? Check the fine print.
Use websites like Confused.com, UCompare.ie and CompareNI as a base to see who can cover you and how much they charge. Then, make a shortlist and visit those sites individually and read the small print for what they actually cover.
You basically want to imagine the worst case scenario, and make sure that whatever policy you choose will cover it. If you choose a policy with a high excess, are you prepared to pay that in the eventuality that you need to?
Also check independent ratings – things like Defaqto can help you quickly gauge whether a provider is broadly reputable. I’ve recently made sure any policy I take out is at least four star Defaqto rated.
What Is Defaqto and Why It Actually Matters
You’ll often see travel insurance policies advertised as Defaqto rated, sometimes with a star score attached. But what does that actually mean?
Defaqto is an independent financial research company that reviews insurance products based on the depth and quality of their cover, not how cheap they are. Their star ratings range from one to five, with five star ratings reserved for policies that offer strong, comprehensive protection across key areas.
Why Defaqto Ratings Are Worth Paying Attention To
A high Defaqto rating usually indicates:
- strong medical cover
- good cancellation protection
- decent baggage and valuables limits
- clear policy wording
- fewer gaps or weak spots
It doesn’t mean a policy is perfect or right for everyone, but it does suggest the cover is well rounded rather than bare bones.
What Defaqto Ratings Don’t Tell You
A five star rating doesn’t automatically mean:
- it’s the cheapest option
- it includes every activity you want
- it covers pre existing conditions
- it includes gadget cover as standard
You still need to read the details. Think of Defaqto as a quality filter, not a final decision maker.
How to Use Defaqto When Comparing Policies
Use the rating to narrow down your options, then compare:
- medical limits
- exclusions
- excess amounts
- add ons
- suitability for your destinations and activities
It’s a smart way to avoid policies that look cheap but fall apart when you actually need them.
What to Look for in a Good Travel Insurance Policy
- Clear, reasonably high medical coverage
- Solid emergency assistance worldwide
- Good baggage/valuables cover (especially if you travel with tech or expensive gear)
- Gadget cover if you carry cameras, laptops, drones etc.
- Flexible trip lengths or multi-trip (if you travel regularly)
- Transparent terms – no sneaky exclusions hidden in the small print (my pal Lizzie on TikTok will attest to this. More on that later)
- Option to cover adventure activities if you do them – skiing, diving, hiking etc.
- Add-ons that make sense for your travel style, not just “everything under the sun”
Annual vs Single Trip Insurance
Annual Multi-Trip Travel Insurance
An annual travel insurance policy is best if you travel more than once a year, like me. This saves the hassle of buying and reviewing cover policies every time you fly, and protects future trips against the unexpected. Great for frequent flyers and people with flexible plans. Always check the maximum trip length allowed per journey though.
Single Trip Travel Insurance
A one-off cover for a single trip is better if you’re doing just one holiday or a big trip. Depending on the provider it may give stronger coverage per trip (for cancellations, luggage etc.) compared to a generic multi-trip.
Traditional Travel Insurance vs Digital Nomad Medical Insurance
Traditional travel insurance is built for holidays and trips: you go, you come back, you go on another trip and come home again… But, if you spend long periods abroad, jump between countries, work remotely or just don’t follow the traditional holiday pattern, nomad-style insurance might be your answer.
This is where digital nomad medical insurance comes into the picture. One of the more well known options in this space is SafetyWing, a provider desigcencned specifically for people who travel long term or live abroad while working remotely. Instead of covering individual trips, SafetyWing works on a rolling, subscription style model that focuses primarily on medical cover, with some travel related protections built in. To show how nomad style insurance actually works in practice, I’m going to use SafetyWing’s Nomad Insurance Essential plan as an example and break down what it covers, how much it costs, and who it’s best suited to.
What SafetyWing’s Nomad Essential Travel Insurance Covers
Instead of covering individual trips and stints abroad, SafetyWing’s Nomad Essential provides rolling medical cover for people who are on the move for longer stretches of time. Shorter term options are also available too, which is good to know. On the website, just click the option for “exact dates” and choose your requirements from there.
Here’s what’s covered by SafetyWing’s Nomad Essential Travel Insurance:
- Cover for up to 364 days at a time
Ideal for long term travel or slow travel without fixed end dates. - Treatment for new, unexpected medical issues while travelling
This focusses on emergencies and sudden illnesses, rather than ongoing care. - Limited medical cover in your home country
Includes up to 30 days of medical cover during short visits back home. - Medical cover that does the essentials well
Inpatient and outpatient treatment, emergency dental, ambulance services, hospital stays, urgent care and repatriation if needed. - Basic travel protection
Cover for lost checked luggage, stolen passports or visas, travel delays or missed flights, trip interruption and emergency accommodation if you get stuck. - Flexible start dates and rolling cover
You can start your policy even after you have already left home and continue cover from as little as five days up to twelve months through renewals or subscription. - Straight forward pricing
For many younger travellers aged roughly 18-39, pricing works out at around US $56.28 every four weeks for non-US travel, which is roughly US $1.87 per day. - Optional add-ons
You can add electronics theft cover for things like laptops and cameras, as well as certain adventure or higher risk activities for an additional cost where available. - Short home country visits included
Useful if you move between home and abroad, with limited home country medical cover included for set periods.
What SafetyWing’s Nomad Insurance Essential Doesn’t Cover
The SafetyWing Essential Nomad Insurance is designed to cover the basics well, but as with all polices, it’s important to know where there are limitations in coverage. Here’s where the limits sit:
- Pre existing conditions are not covered
Ongoing or chronic medical issues are excluded under the Essential plan. - No routine or long term care
Things like regular check ups, specialist appointments, therapies, mental health support and maternity care are not included. However, this option is available with the Nomad Insurance Complete plan - Electronics are not automatically covered
Gadget or electronics theft is only included if you add the optional extra. The standard policy does not guarantee cover for laptops, cameras or similar items. This stands true for most travel insurance policies in my experience. - Medical cover has a cap
With a limit of $250,000 (USD), this may feel low if you are travelling in very high cost countries or expect to need extensive treatment. - Some activities are restricted
Certain high risk or extreme sports may require additional surcharges or may not be covered at all under the Essential plan.
Why Nomad Insurance Makes Sense – and When Traditional Might Still Be Better
Choose Nomad Style Insurance if:
- You’re not doing a standard holiday, but travelling long-term, slow-travelling or bouncing between countries.
- You want a simple, rolling monthly/4-weekly plan with flexibility to start and stop without fixed trip dates.
- You care mainly about medical emergencies and basic travel protection rather than full gadget, cancellation or luxe baggage cover.
- You don’t mind patching some of the gaps (e.g. pre-existing conditions, electronics, certain activities) yourself, or opting for add-ons selectively.
Stick with Traditional Travel Insurance if:
- You’re doing a defined holiday or a series of holidays with clear start and end dates.
- You want wide coverage: cancellation protection, full gadget and baggage cover, higher baggage/valuables limits, and extras like sports or cruise-trip cover.
- You carry expensive gear, travel light or do a lot of flights – theft, delays, lost luggage or cancelled trips are realistic threats.
- You prefer concrete coverage for each trip instead of rolling over month-to-month.
Both options serve different travel styles. It just depends on which suits yours.
What If You Forgot Travel Insurance or Just Need Quick Medical Help?
With the best planning in the world, sometimes things happen beyond your control. Because the truth is: life doesn’t always go to plan. You might forget to buy cover, or your policy might have a high excess, or the insurer might dig their heels in when you call. I’ve been there. And it can still end up absolutely fine – sometimes even easy.
The Time We Went Straight to A&E in Seville
On a trip to Seville, my partner got ill and our insurer was being vague about what they’d actually cover. Instead of waiting on replies, we just went to the hospital. Within a couple of hours we were seen, treated and sent on our way.
The most important lesson: get the care you need – the paperwork can be sorted later.
How I Sorted Medical Help in Valencia Without Insurance Hassle
More recently, in Valencia, I messed up and forgot to bring medication for a pre-existing condition which had flared up. Instead of relying on insurance, I booked a video consultation via the app Doctorsa. Within hours a friendly doctor video-called me, listened, emailed a prescription, and I picked up meds the same afternoon. The call cost €20 and the prescription was the same – tiny compared with the stress (and cost) of trying to claim via an insurer. This was the first time I had ever had a consultation with a doctor while sitting on a park bench with my earbudss in, and I hope it was the last!
If you can’t rely on your policy or simply forgot it, there’s always “plan B”.
Things to Watch Out For With All Travel Insurance
- Gadget or electronics cover may require an add-on (or might be limited)
- Always check if the policy will cover any pre-existing conditions
- Some adventure or high-risk sports need extra fees or aren’t covered at all
- Coverage caps may feel low if you end up in a high-cost country or need extensive treatment
- Don’t rely on “everything’s covered” – read the fine print
As I mentioned earlier, my pal Lizzie got caught out after a long flight delay that racked up a load of extra costs. The airline wasn’t helpful at all, so she assumed her travel insurance would step in. It didn’t. In fact, the insurer offered even less than the airline, pointing straight back to some information that was hidden in the terms and conditions that she hadn’t realised applied.
You can watch her whole saga unfold in the TikTok videos below, but the takeaway is simple. Always read the policy documents before committing. The more you fly, the more likely something will go wrong at some point, so your cover needs to be genuinely fit for purpose, not just cheap and cheerful.
Things to Note Before You Buy
- If you travel often, weigh up long-term cost vs coverage
- Check whether you need gadget cover or adventure add-ons – don’t assume they’re included.
- If you have a pre-existing health condition, be clear on what’s excluded.
- Flight delays and cancellations can happen with short notice. Does your travel insurance policy offer strong protections?
- Think about the type of travel you do: quick holidays, slow travel, digital nomad lifestyle – each benefits different kinds of cover.
- Always read the policy wording carefully. Cheap or easy isn’t the same as good.
Which Travel Insurance Policy I Chose and Why
After bouncing between different insurance providers over the years, I landed on a policy that best fitted how we travel. I was happy with the cover I had with Admiral Travel Insurance last year, so I decided to roll it on for another twelve months.
The policy is Defaqto five star rated, covers both of us for the full year, includes gadget protection and applies to every country we’re planning to visit in the year ahead. From a practical point of view, it just made sense. No re buying cover for each trip, no worrying about gaps, and no second guessing whether we’re protected when we’re hopping between destinations.
It’s not about chasing the cheapest option. It’s about choosing cover that fits your travel style and lets you get on with the fun stuff without overthinking the admin.
That said, this type of annual policy won’t suit everyone. If you only travel once a year, don’t carry gadgets, or prefer paying per trip rather than upfront, a single trip policy or a more flexible nomad style option might be a better fit.
Travel Insurance – FAQ
Does travel insurance cover COVID or illness abroad?
Most modern travel insurance policies cover emergency medical treatment for illness abroad, including COVID, but the level of cover and exclusions vary. Always check the medical section and policy wording to confirm what is included.
Can I buy travel insurance after booking a trip?
Yes. You can usually buy travel insurance at any time, but it’s best to purchase it as soon as you book your trip so you’re covered for cancellations straight away.
Can I buy travel insurance after I’ve already left home?
Some policies allow this, but many traditional travel insurance providers require you to buy cover before departure. Digital nomad style insurance is often more flexible in this area.
Does travel insurance cover lost or delayed baggage?
Most policies cover lost, stolen or delayed baggage, but there are usually limits per item and requirements around reporting delays or theft within a set timeframe.
What counts as a pre existing medical condition?
A pre existing condition is usually any medical issue you’ve had symptoms of, received treatment for, or taken medication for within a certain period before buying the policy. This varies by provider, so always check.
Is alcohol related illness or injury covered?
Some policies exclude alcohol related incidents or limit cover if alcohol is involved. This is one of the most commonly overlooked exclusions.
Does travel insurance cover adventure activities or sports?
Not always. Activities like skiing, diving, hiking at altitude or motorbike hire often require an add on. Always check the activities list before you travel.
Will travel insurance cover me if I miss my flight?
It depends on the reason. Policies may cover missed connections due to delays outside your control, but not if you oversleep or arrive late at the airport.
Does travel insurance cover flight cancellations by airlines?
Insurance may cover additional expenses caused by cancellations, but it doesn’t replace airline obligations. You’ll usually need to claim from the airline first.
Is my phone or laptop automatically covered?
Not always. Some policies include gadget cover, some cap it at low amounts, and others require you to add it separately.
Does travel insurance cover theft without force?
Some policies require evidence of forced entry or a police report. Theft from unattended bags is commonly excluded.
Can I claim if I lose my passport abroad?
Most policies cover the cost of replacing a stolen passport, provided you report it to local authorities and keep documentation.
Does travel insurance cover cruises?
Not all policies do. Cruise cover often needs to be added separately and may include specific benefits like missed port cover or cabin confinement.
Is annual travel insurance cheaper than single trip?
If you travel more than once or twice a year, annual multi trip insurance often works out cheaper. For one off holidays, single trip policies can be better value.
Does travel insurance cover car hire excess?
Some policies include limited car hire excess cover, but standalone excess policies often offer better protection.
What should I do before making a claim?
Contact your insurer as soon as possible, keep all receipts and documentation, and follow the reporting requirements outlined in your policy.
The Small Print
Updating your Travel Insurance isn’t glamorous and it isn’t fun, but it’s one of those “grown up but necessary” moves every traveller should consider. If you travel a lot or don’t have fixed plans, nomad-style medical insurance from something like SafetyWing can offer flexibility, global cover and a simple, rolling safety net.
If you’re doing defined holidays, carrying stuff you care about or need full-on cover (luggage, gadgets, cancellations, adventure add-ons), traditional travel insurance still holds strong.
Bottom line: the best policy isn’t the cheapest or the one with the most extras – it’s the one that matches the way you travel. Read the boring bits, pick accordingly, and don’t get caught out.
Last Updated on 2 months ago by Ryan | Irish Travel Addict
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