If your year is packed with multiple trips, travel insurance can be a smart way to safeguard against unforeseen circumstances like injury or illness. For frequent flyers, especially those who travel for business or go on regular family holidays, the hassle of buying insurance for each individual trip can be cumbersome. This leads us to consider annual travel insurance: what it is, when it's beneficial, and whether it's a worthwhile investment for your travel lifestyle.

Think of travel insurance as your personal safety net when you are away from home, stepping in to provide protection on your international trips. You will find various types and levels of coverage including policies that cover trip cancellations and interruptions, lost luggage, emergency evacuations and more. 

Most travel insurance providers offer different tiers of coverage within these categories, and often allow you to customise a policy to your unique requirements instead of simply accepting the basic package. This allows you to tailor coverage towards the activities you have planned for each trip, such as cruises and high-risk sports. Keep in mind that some policies may cap the number of days per trip.

>> MORE: What is travel insurance?

Wondering how multi-trip insurance differs from single-trip insurance? Let’s take a look at the key points:

Unlike single- and multi-trip insurance, annual travel insurance plans are usually activated from the date of purchase for 12 months. While each individual trip you make during this period is covered, there is typically a cap on the maximum duration allowed per trip.

With an annual plan, your coverage resets for each trip. For example, you get baggage delay coverage for each trip, not just once annually. Take some time to shop around for the most suitable policy – some insurance providers may allow automatic renewals or provide you with a discount for renewal.

>> MORE: Annual vs single trip travel insurance

You may be surprised to learn that an annual or multi-trip travel insurance plan can be quite affordable. Naturally, obtaining quotes is a vital first step before making any purchase, so some upfront research is recommended. To illustrate the potential costs, let’s take a look at the offerings from three popular insurance providers in Singapore.

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Choose from three tiers to suit your coverage needs: Basic, Superior and Prestige. All three tiers cover the essentials including medical expenses, trip cancellation and travel delays, only differing in the maximum payout that will be disbursed. Add-ons such as COVID-19 protection are available.

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With 24/7 emergency medical assistance available worldwide, MSIG TravelEasy provides an attractive annual plan for frequent travellers. If you have pre-existing medical conditions, you can opt for the Pre-Ex plan for additional peace of mind.

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SingLife offers both regional and worldwide coverage tiers to suit the needs of all travellers. Family plans are also available. Making an online claim is easy – simply make sure that you have all the required documentation ready. Within 3 days of your claim submission, you can expect to receive an acknowledgement email and funds will be paid directly to the account linked to your PayNow number.

Considering getting an annual insurance plan? Here are some questions to ask yourself before taking the next step:

How often are you travelling?

Start by considering your travel frequency. Are you a regular traveler who’s often on the go? Do you spend significant time abroad? If your travel is infrequent – perhaps one or two trips a year, each lasting a week or two – the benefits of annual travel insurance may not outweigh the cost. 

Do your trips usually involve risky activities?

Evaluate the cost and potential complications of your trips. Are they expensive? Is there a higher risk of illness or accidents (for instance, if you intend to take part in a high-risk activity such as snowboarding or scuba diving)? Is there a chance of cancellation? 

Keep in mind that annual policies have inherent limitations on the duration of each covered trip. For more intricate or higher-risk travel plans, a single-trip policy often provides more comprehensive protection, including options such as Cancel For Any Reason (CFAR) and trip delay coverage that annual policies may lack or limit.

Are you affected by pre-existing medical conditions?

When considering annual travel insurance, it's important to understand how pre-existing conditions are handled. These are health issues you had before purchasing the policy, which can range from asthma to high blood pressure. Always declare any conditions you have upon purchase to avoid any claim rejections down the line.

Some annual policies will cover unexpected, acute flare-ups of these conditions. Conversely, many policies contain clauses that explicitly exclude any medical expenses arising from pre-existing conditions, making it vital to review the terms carefully. Yet others will offer the option of adding on this coverage to a basic policy.

>> MORE: Best travel insurance for pre-existing conditions in Singapore

Does your credit card come with travel insurance?

Do you know if your credit card offers complimentary travel insurance? Some popular travel credit cards in Singapore, such as the UOB PRVI Credit Card and Citi PremierMiles Card offer cardholders a basic travel insurance plan. To be eligible, keep in mind that you have to settle any travel-related expenses with the credit card that offers you this benefit.

The important thing to take note about such policies is that the coverage may not be as comprehensive as you would like, making it sensible to take a look at your other options.

>> MORE: 6 credit cards that provide travel insurance

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Rates and Fees

>> MORE: The difference between travel insurance and credit card travel insurance

While annual travel insurance can be a convenient option for frequent travelers, it's important to be aware of its limitations. For instance, many plans impose restrictions on the length of individual trips, certain activities are not covered and the claims process can vary by provider. 

A good rule of thumb is to always do your due diligence and read the policy documents carefully. In addition, if you will be overseas for an extended period such as for an exchange programme or work holiday, you may require long-stay insurance instead.

If you are always on the go, multi-trip travel insurance could be a budget-friendly way to get covered. But before you choose a policy, always take some time to review its terms and conditions.

While an annual plan can be kinder to your wallet than single-trip plans, remember that you might be looking at less extensive coverage. Annual policies often prioritise medical situations and in some cases, handle trip hiccups like cancellations or interruptions. If you prefer the flexibility to call off a trip for any reason or if you want extras like baggage protection, a single-trip policy might be more your speed.

One more tip: if you have got a travel credit card tucked away, chances are it comes with some built-in travel perks. Dig into its benefits guide – you might find coverage ranging from emergency medical evacuation to getting reimbursed for trip delays. It's always smart to know what benefits you already have!

How to maximise your rewards

Any travel credit card you get should tick all your boxes. Here are some of our best recommendations:

• Convert points to Emirates Skywards miles: Citi PremierMiles Card

• Comes with 10 annual complimentary airport lounge visits: DBS Vantage Visa Infinite Card

• No foreign transaction fees during peak travel periods (June-July, November-December): Standard Chartered Journey Credit Card

• Provides travel insurance worth up to $1,000,000: Maybank Horizon Visa Signature Card

• Offers complimentary hotel upgrades and unlimited airport lounge access: American Express Platinum Cards