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When is Annual Travel Insurance Worth the Extra Cost?

Alevin Chan

Alevin Chan

Last updated 02 August, 2023

Choosing an annual plan when purchasing travel insurance can garner better value for money, but only if your trip fulfils some important requirements. Here’s how to know whether an annual plan would be worth it.

Annual travel insurance may seem crazy expensive, but they are actually very worth it if you travel very frequently in a year.

Here’s a guide on what annual travel insurance is, and whether you should consider it.

To save even more money on your travels, we’ve got some travel hacks for you! Additionally, try to reduce your expenses by securing cheap flights and saving money on your rental cars.



Table of contents

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When is it worth paying for an annual travel insurance policy?

You can determine whether to choose an annual plan or several single-trip plans with a simple cost comparison.

Let’s say you plan to take three, week-long holidays in the next 12 months. You can go to your favourite travel insurance provider’s website, punch in the details and get a quote for how much your travel insurance would cost.

Of course, you’ll want two sets of figures: one, the total cost of three single-trip plans, and two, the cost of an annual plan. You can then compare both figures.

But wait. What if you want to go to different geographical regions for each trip – say, Thailand, Japan and U.S? You’d notice that each of these single-tips plans would have different premiums – the further you travel, the higher the premiums.

So when you choose your annual plan, which region should you specify? That’s right, you have to choose the farthest destination you plan to travel to, which in this case, would be the U.S. This also means your annual plan would be priced at the costliest tier.



Here are some figures we pulled from Starr TraveLead Travel Insurance. Figures displayed are before discount.

Premiums (single-trip plans, 1 pax, 7 days)

Premiums (annual plan)

Worldwide: S$58.80

Worldwide: S$531.60

Asia-Pacific: S$46.80

Asia-Pacific: S$439.20

Southeast Asia: S$46.80

Southeast Asia: S$411.60

Total: S$152.40

Highest premium: S$531.60

 SingSaver's Starr TraveLead Exclusive Promotion:  Use promo code SS45 to get an exclusive 45% discount when you buy now. Valid till 30 April 2024. Earn a total of 4 miles per S$1 spend on your premium. Valid till 2 May 2024 8:59 am. and T&Cs apply.


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As shown, annual travel insurance plans are significantly costlier, due to the longer period of coverage provided.

Taking the premiums quoted at face value, if we purchased 52 separate 7-day worldwide plans (so as to get one year’s coverage), we would need to spend more than S$3,000.

Of course, nobody would actually do that in real life. And yes, insurers do give you a better rate for longer periods of insurance, but that doesn’t mean annual plans automatically give you the most savings.

To see why, let’s take a look at another scenario.

Annual plan vs 30-day, single-trip plans

Premiums (single-trip plan, 1 pax, 30 days) 

Premiums (annual plan)

Worldwide: S$148.80

Worldwide: S$531.60

Asia-Pacific: S$119.40

Asia-Pacific: S$439.20

Southeast Asia: S$118.80

Southeast Asia: S$411.60

Total: S$387

Highest premium: S$531.60

SingSaver's Exclusive AIG Travel Guard® Direct Promotion:

Single Trip: Receive up to S$68 PayNow and when you buy NOW! (minimum premium of $80). Valid till 30 April 2024. T&Cs apply.

Annual Trip:  Receive $188 PayNow when you apply NOW! (minimum premium of $650). Valid till 30 April2024. T&Cs apply.

Earn a total of 4 miles per S$1 spend on your premium. Valid till 2 May 2024 8:59 am. and T&Cs apply.


So let’s say you’re lucky enough to take three, 1 month-long holidays this year. You’d be paying a total of S$387 to cover your three trips. This is still a lot less than going for an annual plan.

And why 30 days? Because annual plans will typically only cover you for 30 days on any single trip you take. Beyond that you will not be covered – even though your annual plan is valid for 12 months.

Hence, if you’re planning a two-month winter retreat to Japan, your annual plan will only cover the first 30 days of your trip – leaving you without coverage halfway through! You’d be better off purchasing a single-trip plan to cover the entire two months you’ll be spending overseas.

Note that this 30-day restriction is common, but not universal. Some insurers may offer longer coverage-per-trip under their annual policies. As always, check with your insurer to be completely sure.

SingSaver's Exclusive FWD Promotion: Use the promo code TRAVEL25 to get a 25% discount on Single Trip and Annual Trip plans! Valid till 15 April 2024. T&Cs apply.

Earn a total of 4 miles per S$1 spend on your premium. Valid till 2 May 2024 8:59 am. and T&Cs apply.



Who should get an annual travel plan?

Given the high premiums and restrictions on coverage-per-trip, who are annual travel insurance plans actually meant for?

Well, it would appear that annual travel plans are made for travellers who travel frequently, taking perhaps 10 or more trips in a year. Their trips would also tend to be short, maybe around a week or so.

Hence, annual plans do seem to be made for business travellers or corporate staff that need to fly from one regional office to another.

Of course, if you happen to be a person-of-leisure and frequently fly to Tokyo for sushi Saturdays, then an annual plan is likely to offer the best value to you too.

On the other hand, leisure travellers who fly less frequently and may stay overseas for longer durations, would likely find single-trip plans to be a more suitable choice.

An ex-Financial Planner with a curiosity about what makes people tick, Alevin’s mission is to help readers understand the psychology of money. He’s also on an ongoing quest to optimise happiness and enjoyment in his life.


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