Annual vs Single-Trip Travel Insurance in 2025: Which Should You Choose?

When planning travel, one of the key decisions is how to insure yourself: a single-trip policy covering one holiday, or an annual (multi-trip) policy covering all or many trips within a year. In 2025, the decision still comes down to your travel habits, destinations, and risk profile—here’s a breakdown of the main factors.

What’s the difference?

• A single-trip policy covers one specific journey from start to finish (for example, a 10-day holiday abroad).
• An annual (or multi-trip) policy covers multiple trips over a 12-month period, typically up to a maximum duration per trip (for example, trips up to 30, 45 or 90 days each).

Advantages & disadvantages

Single-trip: pros

• Usually cheaper if you are only taking one holiday in the next year. Compare
• Coverage can be tailored exactly for that one trip (duration, destination, add-ons like adventure sports).
• May allow longer single trips than annual plans (some annual policies limit each trip’s length).

Single-trip: cons

• If you take more than one trip, you’ll need a new policy each time, which may cost more in total than an annual policy.
• Less convenience since you must purchase each time you travel.

Annual: pros

• Convenience: buy once and be covered for multiple trips over a year.
• Often better value if you travel multiple times a year: cost per trip goes down.
• Good for business travellers or frequent flyers who don’t want to buy a policy for each trip.

Annual: cons

• Up-front cost is higher than a single policy for one trip.
• Many annual plans have trip-duration limits (e.g., each trip cannot exceed 30/45/90 days) so they are not ideal for long-stay travel.
• Coverage may be less flexible for add-ons (e.g., adventure sports, high value cancellation cover) compared to single-trip options.
• If you rarely travel, you may pay for many unused trips.

When does annual become a better deal?

In 2025, industry data suggests that the “break-even” point is around two to four trips per year, depending on trip length and destination. For example, one study cited that after three to four overseas trips, annual multi-trip cover became cheaper than buying separate single-trip policies.

Another comparison shows that, for Europe-only travel, a single-trip policy for one week might cost the same as an annual policy, but if you do two, three or four trips the annual per-trip cost falls substantially.

So if you travel multiple times a year (say business + holiday), the annual option is more likely to be cost-effective.

Key considerations for travellers from UK (or similar markets)

• Destination scope: If your trips vary wildly (local, regional, inter-continental), check whether the annual policy covers all destinations you plan. Some annual plans may exclude certain high-risk countries or limit worldwide cover.
• Trip duration: If you plan a long stay (e.g., more than 90 days) or a one-off extended trip (study abroad, sabbatical), a single-trip policy might be more appropriate because many annual plans lock in shorter max durations per trip.
• Pre-existing medical conditions: Disclosing health conditions is critical. Some annual policies may have stricter exclusions or may not offer cancellation cover for pre-existing issues. Single-trip policies may offer more tailored cover in such cases.
• Budget and flexibility: If you only travel once a year (or rarely), then a single-trip policy means you don’t pay for unnecessary coverage.
• Add-ons and coverage types: If you need extras (e.g., adventure sports, high-value equipment, trip-cancellation for any reason), check whether these are available or included. Annual policies sometimes provide more basic cover for these items.

Practical steps for choosing in 2025

1. Estimate how many trips you’ll take this year, their likely duration, destinations and activities.
2. Get quotes for both single-trip (for each planned trip) and an annual multi-trip policy covering all your expected travel.
3. Compare not just price, but what’s covered (medical, cancellation, baggage, adventure sports) and limits per trip (max days), as well as any additional restrictions (age limits, destination exclusions).
4. Read the policy “small print” carefully — many rejected claims relate to non-disclosure of conditions, misunderstanding trip limits or activity exclusions. The Sun+1
5. Choose the option that gives you peace of mind with the right level of cover and cost-effectiveness.

If you travel once or maybe twice a year, especially if one of those trips is long or involves special activities, a single-trip policy likely makes sense. If you travel multiple times a year and want simplicity and lower cost per trip, then an annual (multi-trip) policy may be smarter.

Ultimately, the decision in 2025 is less about “which is always better” and more about matching your travel habits, risk tolerance and budget to the policy features. Do the math, compare carefully, and you’ll pick the plan that gives you protection (and peace of mind) without overpaying.