Staysure Travel Insurance Review 2026: Our First-Hand Experience
Travel insurance is one of those things we hope we never need to use. But when you travel regularly, particularly several times a year, having the right policy can become just as important as booking flights or accommodation.
Our Staysure travel Insurance review: What We Bought.
This is not a review based purely on reading insurance comparison websites. We actually purchased a Staysure policy for ourselves in June 2026, covering two travellers for worldwide trips for a full year.
In this Staysure Travel Insurance review, we explain what we bought, what we paid, what our policy included, why we chose annual multi-trip cover and what we think travellers should check carefully before buying.
We will also look at whether Staysure could make sense for travellers over 50, couples taking several holidays a year and people looking for cover for pre-existing medical conditions.
Important: Travel insurance policies, prices, limits and exclusions can change. The figures relating to our own policy below describe the policy we personally purchased in June 2026. Always check the latest policy wording and your own validation certificate before buying or travelling.
Quick Facts: Our Staysure Travel Insurance
Provider: Staysure
Policy type: Annual Multi Trip
Cover level: Comprehensive
Destination: Worldwide
Number of travellers: Two
Policy purchased: June 2026
Duration: 12 months
Total we paid: £199.15
Cancellation limit on our policy: £5,000
Emergency medical and repatriation expenses on our policy: Unlimited
Winter sports: Included on our validation certificate for two trips, up to 21 days in total
Cruise: Not covered on our policy
Maximum individual trip length for us: 50 days
Maximum travel during the policy year: 183 days in total
This Staysure Travel Insurance review is based on the exact policy we purchased and used for own travels
These are the terms shown on our own validation certificate, not a promise of what another traveller will receive.
Your quote and cover may be very different depending on your age, destination, medical history, level of cover, optional extras and other underwriting factors.
Why We Chose Staysure Travel Insurance
We travel regularly rather than taking just one holiday each year.
That immediately made annual multi-trip insurance worth considering.
Instead of arranging a new policy before every European break, weekend away or longer international trip, an annual policy gives us one set of cover for multiple eligible trips during the policy year.
Staysure’s current Annual Multi-Trip Travel Insurance is designed for this type of traveller. Its standard annual policy allows up to 183 days of travel in total during 12 months, subject to individual trip limits.
Convenience was therefore a major factor for us.
There was another reason Staysure caught our attention: it specialises heavily in travel insurance for older travellers and people with medical conditions.
Staysure currently states that there is no upper age limit on its senior travel insurance and that it can cover more than 1,300 pre-existing medical conditions, subject to its medical screening and policy terms.
For travellers in their 50s and beyond, that makes Staysure an obvious provider to at least include when comparing quotes.
Our verdict at a glance
For us, the combination of annual worldwide cover, the ability to insure multiple trips and substantial emergency medical cover made the policy attractive.
However, we would not recommend choosing any travel insurer solely because it worked for us.
Travel insurance is highly individual. A cheap policy with the wrong exclusions can be poor value, while a more expensive policy that properly covers your circumstances may be considerably more useful.
Our recommendation is simple: compare the actual cover, exclusions and excess — not just the headline price.
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What Staysure Policy Did We Actually Buy?
We purchased a Staysure Annual Multi Trip Comprehensive policy.
Our geographical cover was Worldwide – All Countries, and the policy covered both of us.
This distinction matters because Staysure offers different types and levels of insurance. Someone purchasing Basic cover, for example, should not assume they have exactly the same benefits as someone purchasing Comprehensive or Signature cover.
Staysure currently advertises three principal levels of cover: Basic, Comprehensive and Signature. The limits and included benefits vary significantly between them.
Our validation certificate is therefore the basis for everything we say about our policy in this review.
How Much Did Our Staysure Travel Insurance Cost?
We paid:
£199.15 in total for two people for one year.
That covered our Annual Multi Trip Comprehensive policy with worldwide geographical cover.
However, there is an important point here.
£199.15 is not “the price of Staysure travel insurance”.
It was our individual quote.
Travel insurance pricing can depend on numerous factors, including:
- age;
- destination;
- single-trip or annual cover;
- level of cover;
- medical conditions;
- optional extras;
- trip duration;
- number of travellers.
So we would not use our £199.15 price as a benchmark for what you should expect to pay.
The only reliable way to know your price is to obtain your own quote.
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What Was Included in Our Staysure Comprehensive Policy?
Our validation certificate showed several particularly important benefits.
£5,000 Cancellation Cover
Our policy certificate stated a £5,000 cancellation limit.
Cancellation cover can be important when you have already paid significant amounts for flights, accommodation, tours or other non-refundable travel arrangements.
But cancellation insurance does not mean you can simply decide not to travel and automatically receive your money back.
Claims are governed by specific covered reasons, conditions and exclusions in the policy wording.
Staysure’s May 2026 policy wording, for example, states that a cancellation reason must be covered by the policy, occur during the relevant period of cover, be beyond the insured person’s control and be unexpected.
This is exactly why we recommend reading the actual policy documents rather than relying on a short marketing summary.
Unlimited Emergency Medical and Repatriation Expenses
Our validation certificate stated:
Emergency Medical and Repatriation Expenses: Unlimited
For us, this was one of the most important parts of the policy.
A lost suitcase is inconvenient. An unexpected medical emergency abroad can potentially be far more serious and expensive.
Staysure’s current Comprehensive cover also advertises unlimited emergency medical and repatriation expenses, although the full terms, exclusions and eligibility requirements still apply.
That does not mean every medical expense in every situation is automatically covered.
You still need to understand the policy terms and, critically, correctly declare relevant pre-existing medical conditions.
Pre-Existing Medical Conditions: Read This Carefully
This is one area where we would strongly advise against rushing through the quotation process.
Staysure is particularly well known for offering insurance to older travellers and people with existing medical conditions.
The company currently says it can cover more than 1,300 pre-existing medical conditions, subject to medical screening.
But the important word here is declare.
Our own Staysure documentation specifically warns policyholders to check that medical conditions have been declared and that incorrect or incomplete answers may invalidate a potential claim.
So if you have a medical condition, do not try to make your quote cheaper by leaving information out.
Answer the medical screening questions accurately.
If you are unsure whether something needs to be declared, check directly with the insurer rather than guessing.
That applies not just to Staysure but to travel insurance generally.
Staysure Annual Multi-Trip Insurance: How Does It Work?
For frequent travellers, this was one of the most attractive parts of the policy.
Instead of buying separate insurance for every holiday, annual multi-trip insurance covers eligible trips during a 12-month period, subject to the policy’s geographical area, maximum trip duration and other terms.
Staysure currently states that Annual Multi-Trip policies can cover up to 183 days of travel in total during the year.
For travellers aged 70 or under, the standard individual trip limit is currently 50 days. For travellers aged 71 and over, it is 35 days. Staysure also says eligible travellers aged 70 or under can pay to extend one trip to as much as 100 days.
Our own validation certificate showed a maximum of:
50 days in one trip, with no more than 183 days of travel in total during the policy period.
That suited the way we travel.
If you normally take several holidays or city breaks each year, an annual policy can also remove the repetitive task of arranging insurance every time.
Staysure says you do not need to inform it about each individual trip provided you stay within the agreed policy limits.
Annual Multi-Trip vs Single-Trip Travel Insurance
Neither is automatically better.
The right choice depends on how you travel.
Annual Multi-Trip May Suit You If:
You expect to travel several times during the next 12 months.
For example, you might take:
a spring city break, a summer holiday in Spain, an autumn trip elsewhere in Europe and a winter getaway.
Having one annual policy can be much more convenient.
Single-Trip May Suit You If:
You are only planning one holiday or need cover for a trip that does not fit the duration or geographical limits of an annual policy.
Staysure currently says its standard Single Trip Travel Insurance can cover trips of up to 104 days, although duration limits can depend on age, destination and policy type.
The sensible approach is to obtain both types of quote if you are unsure.
Do not assume annual insurance is cheaper simply because you have two trips planned. Compare the actual prices and cover.
Is Staysure Good for Travellers Over 50?
This is probably one of the strongest reasons people encounter Staysure in the first place.
Staysure specifically markets travel insurance for travellers in their 50s, 60s, 70s, 80s and beyond.
There is currently no upper age limit on its senior travel insurance.
That is significant because travel insurance can become more complicated and expensive with age, particularly where medical conditions are involved.
Staysure also positions itself as a specialist in medical travel insurance.
That does not mean it will automatically be the cheapest or best insurer for every traveller over 50.
It means it is a provider we think is worth including in the comparison.
The final decision should come down to:
price + cover + medical acceptance + excess + exclusions + destination + trip duration.
Not brand name alone.
Winter Sports Cover on Our Policy
Our validation certificate states:
Winter Sports Cover: 2 trips up to 21 days in total.
This was included on our particular Annual Multi Trip Comprehensive certificate.
If skiing or other winter sports are important to you, check this carefully when obtaining a quote because cover can depend on the policy level, activity and current terms.
Do not assume that every activity you might describe as a “winter sport” is automatically insured.
Always check the activity list and exclusions.
What About Cruises?
This is another good example of why reading the validation certificate matters.
Our certificate explicitly stated:
Cruise: Not covered.
For us, that is clear.
If we wanted cruise-specific protection, we would need to check and arrange appropriate cover rather than assuming our existing policy included it.
Staysure currently says cruise cover can be added to Annual Multi-Trip insurance for an additional fee.
So if you are buying insurance specifically for a cruise, check the cruise option during the quotation process.
Do You Need to Tell Staysure Every Time You Travel?
According to both our policy documentation and Staysure’s current guidance, generally no, provided your cover details have not changed and your trip remains within the policy’s limits.
Our certificate specifically states that we do not need to inform Staysure when travelling provided our cover details have not changed.
Staysure’s Annual Multi-Trip guidance similarly says policyholders do not need to report each trip as long as they remain within their agreed trip limits.
For frequent travellers, we find this useful.
Book the trip, confirm that the destination and duration fall within the policy, and make sure nothing relevant has changed.
FCDO Travel Advice Matters
This is an important point that travellers sometimes overlook.
Our Staysure documentation states that if, when a trip begins, the UK Government or Foreign, Commonwealth & Development Office advises against all travel or all but essential travel, the policy will not provide cover in the circumstances described in our certificate.
Travel advice can change.
Therefore, before travelling — particularly to a destination affected by political instability, natural disasters or other major events — check the latest FCDO advice and your insurance terms.
Insurance should never be treated as permission to ignore official travel warnings.
What We Like About Staysure So Far
We need to make an important distinction here.
We have purchased and used the policy as travel cover, but this review is not based on having made a claim.
Therefore, we cannot tell you that Staysure’s claims handling is excellent or poor from personal experience.
That would not be an honest first-hand claim.
What we can assess is the purchasing decision, policy structure and documentation we received.
One policy for multiple trips
For frequent travellers, this is the main attraction.
We do not need to purchase a separate policy every time we take an eligible trip.
Worldwide cover was available
Our chosen policy covers the worldwide geographical area stated on our validation certificate.
That gives us more flexibility than buying insurance specifically for one European holiday.
Strong emergency medical limit on our policy
Our certificate shows unlimited emergency medical and repatriation expenses.
That was important to us.
Suitable for travellers over 50
Staysure has a clear focus on older travellers and currently has no upper age limit on its senior travel insurance.
Medical conditions can be considered
Staysure currently says it can cover more than 1,300 pre-existing medical conditions, subject to screening.
Clear validation certificate
We like having the major limits clearly stated on the certificate: geographical area, policy type, trip duration, cancellation limit and medical cover.
What Could Be Better?
No travel insurance policy should be presented as perfect.
The documentation needs to be read carefully
Travel insurance contains conditions and exclusions. The validation certificate is only part of the documentation.
You still need the full policy wording.
Optional activities need checking
Cruises are a good example. Our own certificate says cruise cover is not included.
If your holiday involves skiing, cruises, golf, gadgets or other specific risks, do not assume they are covered.
Your price may be completely different from ours
Our £199.15 price sounds useful as a real-world example, but it tells you very little about what your own quote will cost.
We cannot judge the claims experience
We have not made a claim.
For that reason, we are deliberately not giving Staysure a claims-handling rating based on other people’s experiences and presenting it as our own.
For a genuine first-hand Two Horizons review, that distinction matters.
Pros and Cons of Staysure Travel Insurance
Pros
Annual multi-trip option – convenient for people travelling several times each year.
No upper age limit – particularly relevant for older travellers.
Pre-existing medical conditions considered – Staysure says it can cover more than 1,300 conditions, subject to screening.
Substantial medical cover available – current Comprehensive policies advertise unlimited emergency medical and repatriation expenses.
Different levels of cover – Basic, Comprehensive and Signature options allow travellers to choose different levels of protection.
Worldwide options – useful for travellers who do not only visit Europe.
Cons
Not necessarily the cheapest option – specialist cover does not automatically mean lowest price.
Policy details require careful reading – exclusions and limits matter.
Some cover requires optional extras – depending on the activity and policy.
Annual policies still have trip-duration limits – annual does not mean unlimited travel.
Medical information must be declared accurately – incomplete declarations can cause serious problems if you later need to claim.
Who Do We Think Staysure Is Best For?
Based on our experience purchasing the policy and the cover Staysure currently offers, we think it is particularly worth investigating if you are:
over 50 and travel regularly;
taking several holidays each year;
looking for annual multi-trip insurance;
travelling as a couple;
looking for worldwide rather than Europe-only cover;
or
looking for an insurer that considers pre-existing medical conditions.
That does not mean Staysure will automatically be your best option.
We would still compare at least a few quotes.
Is Staysure Travel Insurance Worth It?
For our travel pattern, we were comfortable buying it.
We paid £199.15 for two travellers for an Annual Multi Trip Comprehensive worldwide policy.
Because we travel multiple times a year, the convenience of one annual policy was important.
The emergency medical and repatriation limit shown on our certificate was also a major consideration.
But whether Staysure is worth it for you depends on the quote and terms you receive.
If another insurer offers substantially better cover for your circumstances at a similar price, choosing Staysure simply because you recognise the brand would make little sense.
Likewise, choosing the absolute cheapest quote while ignoring medical cover, cancellation limits and exclusions can be a false economy.
Our approach is:
Decide what cover you actually need first. Compare policies second. Compare prices third.
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Our annual policy cost £199.15 for two people, but your price may be completely different.
Get your own quote and check the current cover, limits, excess and exclusions before deciding.
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Staysure Travel Insurance FAQ
Is Staysure travel insurance only for over-50s?
No. Staysure offers travel insurance across different ages, although it has a particularly strong focus on older travellers. Its current senior travel insurance has no upper age limit.
Does Staysure cover pre-existing medical conditions?
Staysure currently says it can cover more than 1,300 pre-existing medical conditions, subject to medical screening and policy terms. You must declare relevant conditions accurately.
How much did we pay for Staysure travel insurance?
We paid £199.15 in total for two travellers for our Annual Multi Trip Comprehensive worldwide policy purchased in June 2026.
This was our personal quote and should not be treated as an indication of what another traveller will pay.
How many trips can you take with Staysure Annual Multi-Trip Insurance?
Staysure says its Annual Multi-Trip policy covers multiple eligible trips over 12 months, with up to 183 travel days in total. Individual trip-duration limits also apply.
What is the maximum trip length?
Staysure currently states a standard maximum of 50 days per trip for travellers aged 70 or under and 35 days for travellers aged 71 or over on Annual Multi-Trip policies. Other options and upgrades may be available.
Our own certificate gives us a maximum of 50 days in one trip.
Does Staysure cover cruises?
Cruise cover was not included in our policy. Staysure currently states that cruise cover can be added to Annual Multi-Trip policies for an additional fee.
Check your own quote and validation certificate.
Does Staysure include winter sports?
Our particular Comprehensive Annual Multi Trip certificate includes winter sports cover for two trips of up to 21 days in total.
Do not assume your policy will be identical. Check the latest quote, permitted activities and policy wording.
Do we need to tell Staysure before every holiday?
Our documentation says we do not need to inform Staysure each time we travel provided our cover details have not changed. Staysure’s current Annual Multi-Trip guidance also says individual trips do not need to be reported as long as they remain within the agreed limits.
Have we ever made a Staysure claim?
No.
Therefore, this review does not rate Staysure’s claims service from first-hand experience. If we ever need to make a claim, we can update this article with what actually happened.
Would we buy Staysure again?
Based on the purchasing experience and the policy we received, we would consider Staysure again and compare its quote against other suitable insurers when renewal time comes.
We would not renew automatically without checking the new premium and policy terms.
Final Verdict: Our Staysure Travel Insurance Review
For travellers taking several holidays a year, particularly couples and travellers over 50, Staysure is worth including on the shortlist when comparing travel insurance.
Our own experience gives us something more useful than a theoretical comparison: we actually chose Staysure and paid £199.15 for an Annual Multi Trip Comprehensive worldwide policy covering two people.
We liked the convenience of annual cover, our worldwide geographical coverage and the substantial emergency medical and repatriation cover shown on our certificate.
But travel insurance is highly personal.
Our policy is not necessarily the policy you will be offered.
Check the current price, medical declarations, geographical region, cancellation cover, excess, maximum trip duration, activities, optional extras and exclusions before buying.
For us, Staysure made sense.
For you, the right answer should come from comparing the actual policy you are being offered — not simply copying our choice.
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Disclosure: We purchased the Staysure policy discussed in this article ourselves. This article is based on our own experience and policy documents. If you purchase insurance through one of our affiliate links, Two Horizons may receive a commission at no additional cost to you. This does not affect the price you pay or our editorial opinion.
This article is for general information and describes our personal experience. It is not financial or insurance advice. Always check the insurer’s latest policy wording, exclusions and your individual validation certificate before purchasing or travelling.
