How to build a travel insurance checklist before you book your holiday

Planning a holiday is usually the fun bit. I can spend an unreasonable amount of time comparing hotel balconies, then leave the travel insurance until the night before departure. That is exactly backwards. The useful policy is the one that matches the trip, your health and the money you would genuinely struggle to lose. In this guide I am walking through a practical way to choose Staysure cover, with the provider’s current options as the examples.

The figures below come from the information currently shown by Staysure. A quote can change with your age, destination, dates, medical screening and optional extras, so treat the limits as a comparison starting point rather than a promise of your personal price. If you want to begin with the main range, you can compare Staysure travel insurance and keep the policy wording open while you work through the checks.

Make a trip snapshot before you compare policies

First, write down the shape of the holiday in one sentence. Mine might say: “A ten-day Mediterranean cruise, two travellers, non-refundable flights, pre-existing medication and a camera in the hand luggage.” That sentence immediately tells me more than a generic search for cheap cover. Trip type drives the shortlist, and it stops a persuasive headline from doing all the thinking for me.

• Destination: record every country, including places where you only change planes or dock.
• Dates: include the full time away and any non-refundable booking made before departure.
• Travellers: note ages, relationships and whether everyone needs the same cover.
• Activities: add skiing, golf, excursions, scooters or anything beyond ordinary sightseeing.
• Valuables: list phones, cameras, jewellery and luggage that may need separate limits.

This is where I decide whether a one-off policy or an annual policy deserves attention. For one carefully defined holiday, Staysure single-trip cover is the cleaner comparison because it is built around that departure and return. If I already know I will take several trips, I also check Staysure annual multi-trip cover rather than buying several separate policies and hoping the dates line up. I can also start the Staysure quote once those dates are ready. The same quote journey shows me what my own dates cost.

Check the medical questions while you still have the booking details

Medical screening is the step I would never rush. Declare conditions accurately, including anything that feels stable or well controlled, and have medication names, recent treatment and dates to hand. Staysure says it can cover 97% of people, including many travellers with pre-existing medical conditions, but the result still depends on the answers in your quote. I would check the live Staysure price only after gathering that information.

Use the provider’s medical travel insurance guidance to understand the kind of information you may need. I would not rely on a broad phrase such as “heart problem” or “old operation” when a screening question asks for a diagnosis, medication or date. If the form asks about symptoms, investigations or a planned procedure, answer that question rather than guessing what seems relevant. The Staysure screening form is easiest to complete when those notes are nearby.

1. Gather prescriptions, condition names and approximate diagnosis dates.
2. Answer every screening question for each traveller, even if one person feels perfectly well today.
3. Save the medical declaration and check that changes before departure are reported.
4. Read exclusions and excesses in the wording, not only the quote summary.

This is also the point where age matters. There is no upper age limit on single-trip cover as shown by the provider, and specialist options are available for older travellers. If that is relevant to your party, compare the details for Staysure over 50s travel insurance alongside the general quote. It is a small extra check that can prevent an awkward assumption later, before you request a personalised Staysure quote.

Choose the cover level by the cost of a bad day

Next I compare the three cover levels against the most expensive realistic problem on the trip. The current Staysure information lists Signature with up to £10,000 cancellation cover per person, plus useful features such as gadget cover and zero excess. Comprehensive lists up to £5,000 cancellation cover per person, while Basic lists up to £500 and does not include every feature. The exact terms and exclusions matter, so I use the Signature and Comprehensive comparison before making a decision.

• Pick Signature for a high-value booking: consider expensive accommodation, several pre-paid elements or a preference for the higher cancellation limit.
• Pick Comprehensive for balanced cover: it may suit a straightforward holiday where £5,000 per person reflects the money at risk.
• Use Basic cautiously: the lower cancellation limit can be quickly overtaken by flights and accommodation.
• Do the maths: add the non-refundable costs for each traveller rather than choosing by the policy name.

Both Comprehensive and Signature are described as offering unlimited medical cover and emergency expenses, with repatriation cover and 24/7 emergency assistance. That is a strong reason to look beyond the cheapest number, particularly for destinations where treatment could be costly. I also open the Staysure policy documents and check the wording for the destination and activity I have entered. Then I return to the Staysure quote to check the premium.

My rule is simple: insure the financial risk I cannot comfortably absorb. If the holiday cost is £1,800 per person, a £500 cancellation limit is not really protecting the booking. If the trip is inexpensive and flexible, a lower level might be sufficient, but I still check medical, baggage and emergency limits rather than assuming “basic” means “enough”. Then I compare the Staysure cover options against that total.

Add only the extras that match the itinerary

Extras should follow the trip, not the other way around. A cruise is the obvious example. Port changes, missed departures and treatment at sea can create different risks from a city break, so I look at Staysure Cruise Plus if I am booking a cruise. The page describes it as a dedicated option, and the quote is where I can see the price and eligibility for my dates. I can price the Staysure option after entering the itinerary.

Winter sports are another definite rather than a maybe. If I am skiing, I check Staysure winter sports cover and make sure the activities, equipment and piste restrictions match the plan. I would not assume a standard policy quietly includes every snow activity. Likewise, a golf holiday deserves a look at Staysure golf cover if clubs, green fees or a golfing itinerary form a meaningful part of the booking.

• Cruise: compare Cruise Plus and check missed-port or itinerary wording.
• Skiing: confirm winter sports cover before paying for lift passes or lessons.
• Gadgets: compare the single-item limit, excess and proof requirements at Staysure gadget cover.
• Disruption: check what happens after a long delay through Staysure travel disruption cover.

For gadgets, I photograph serial numbers and keep receipts somewhere accessible. For baggage, I compare the total limit with what is actually in my case. Staysure’s homepage currently highlights up to £500 for delayed baggage expenses and up to £5,000 if baggage is lost, but those figures are subject to the policy terms. A tidy inventory makes any claim easier to explain, whether I use the Staysure claims guidance or review the cover before departure.

Finish the quote, then save the evidence

Once I have chosen the level and extras, I complete the quote with the exact destination, dates and traveller details. I check the excess, cancellation amount, baggage limit, medical declaration and activity wording on the final screen. The cheapest quote is not automatically the best value if it leaves a large gap beside the booking I am protecting.

1. Compare the final premium with the total non-refundable holiday cost.
2. Confirm every traveller and date is correct.
3. Read the key exclusions and excess before payment.
4. Save the policy number, emergency assistance details and documents offline.
5. Tell the provider about relevant changes before you travel.

I save the certificate as a PDF, email a copy to my travel companion and keep the emergency number in my phone. Staysure advertises 24/7 emergency assistance, and its Travel Doctor service may provide access to English-speaking doctors or specialists abroad with no charge or excess in the circumstances described on the Travel Doctor page. I would still check availability and the full terms for the destination, because a service can have geographical restrictions. Once satisfied, I complete the Staysure application with the final details.

My five-minute pre-departure check

The final check is deliberately boring, which is exactly why it works. I open the saved documents and match them against the trip snapshot. If the itinerary has changed, I update the policy rather than hoping the original quote stretches to fit. I also check that valuables and activities have not quietly outgrown their limits.

• Is the destination listed correctly, including all countries visited?
• Have all medical conditions and changes been declared?
• Are cancellation limits realistic for the bookings?
• Are cruise, winter sports, golf or gadget extras included where needed?
• Can I find the policy number and emergency assistance contact without internet?

That process leaves me with a much clearer answer than simply asking which insurer is cheapest. Staysure feels like a natural shortlist for varied travellers because it brings together single-trip, annual, senior, medical, cruise and activity options. The sensible choice still depends on the quote and wording for the individual trip. My own order is medical accuracy first, financial limits second, relevant extras third and price fourth. I would review the final Staysure quote once more before paying.

If you are ready to compare your own dates, use the quote to test the details rather than treating this guide as a substitute for the policy wording. Start with your trip snapshot, answer the medical questions carefully and save everything once the cover is in place. That is how I turn a vague “I should get insurance” task into one completed before the suitcase is packed.

For an extra practical check, I would compare the quote once with the booking total and once with the activities planned. If both versions make sense, I am comfortable moving forward with Staysure and keeping the documents close at hand. You can see your Staysure quote when the checklist is complete.