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● I still remember planning a trip to South Korea at the beginning of the year, but nothing has been finalised until now. And just another day, I was also discussing with a friend about travelling at the end of this year, and she asked me if she should get single-trip travel insurance or Annual trip travel insurance as she’s expecting to take at least three work trips this year and will also be taking multiple overseas vacations this year. There are many considerations, not just price, and I know most of us are who don’t really compare rates. So, this article is for those wondering whether they should get single-trip or Annual-Trip travel insurance! Check out Single Trip travel insurance that allows you to add multiple countries at once: Annual travel insurance, sometimes known as multi-trip travel insurance, provides coverage for an entire calendar year and is an ideal option for individuals who frequently embark on multiple trips throughout the year. It offers an economical solution for those who travel often, as the cost is spread over numerous trips. With annual coverage, you can also enjoy the convenience and flexibility of being insured for both planned and spontaneous trips without the need to purchase insurance separately for each journey. This type of policy ensures continuous coverage for all trips taken within the policy period. However, a maximum duration may be allowed for each trip, typically 30 to 60 days. On the other hand, single-trip insurance is tailored to provide coverage for a specific journey or vacation—most of the time not exceeding 180 to 182 calendar days overseas, depending on the insurer. It’s suitable for individuals who don’t travel often and can be as short as two days. This insurance option offers an economical option for individual trips, allowing you to purchase coverage tailored to the dates and duration of their particular journey. It also provides flexibility, with coverage starting at the departure and ending upon returning home, ensuring you are protected throughout your trip. It’s a convenient choice for those who only require insurance for a specific journey without the commitment of an annual policy. Besides core coverage for medical emergencies, trip cancellation/interruption, and shared risks, annual trip insurance may offer higher overall coverage limits as multiple trips are accounted for throughout the year. Similarly, when it comes to services, annual travel insurance policies may offer additional benefits such as travel medical assistance, concierge services, or coverage for frequent flyer miles. In contrast, single-trip insurance policies may have fewer (additional) benefits than annual policies due to their focus on covering a single trip. Typically, single-trip travel insurance is more budget-friendly than annual travel insurance. Nonetheless, an annual travel insurance plan might yield greater cost efficiency if your itinerary entails frequent or multiple trips within a year, depending on where you’re headed and for how long. For instance, if you anticipate visiting our closest neighbour, Malaysia, at least once a month due to the long weekends and a favourable exchange rate, with each trip spanning at least five days, the costs of 12 single-trip insurance policies and a single annual plan will differ. While 12 trips per year may seem like an exaggeration, it’s not entirely impossible as many Singaporeans travel to Malaysia daily, especially during weekends. Just this year alone, I’ve been to Malaysia three times. You get what I mean. Let’s see some examples:     The premiums for 12 Single Trips to Malaysia are slightly more expensive than an Annual Trip in this case. But if you’d lower the number of trips to eight, it would be slightly cheaper. However, in another likely scenario, someone would be travelling about three times a year (Australia, South Korea, Thailand), each time being seven days: $26.51 (Austalia) $26.51 (South Korea) $24.62 (Thailand) ASIA (including Australia & New Zealand): $207.62 WORLDWIDE (excluding USA): $257.65 WORLDWIDE: $259.82 $39.60 (South Korea) $34.20 (Thailand) ASIA: $280.40 WORLDWIDE: $360.60   As you can see, even when three trips are taken, the total is still significantly lower than annual trips. Even if you plan to travel to different regions within the same year and less than five times a year, getting Single-Trip travel insurance each time you travel is still more worthwhile. Travel encompasses various modes and destinations beyond air travel. Sometimes, you (and I) may neglect that crossing the border into Johor Bahru, diving on Tioman Island in Malaysia, or crossing the sea to visit places like Batam and Bintan are also considered travelling. Trips to nearby destinations or within the region also pose risks, so you should consider travel insurance unless you work there and your company provides adequate coverage. When making a decision on whether you should be getting Annual or Single Trip travel insurance, these are some guiding principles: As pointed out, Multi-trip or Annual travel insurance may be more cost-effective than single-trip insurance for frequent travellers constantly moving between countries. Most working adults would probably be unable to take as many trips unless they work remotely from overseas. So, if your trips are uncertain, Single-Trip plans will be more suitable due to their flexibility. I’d suggest to cover for every single trip you’re taking. As mentioned above, unless you’re not working in Singapore and your company covers your insurance overseas, getting yourself covered is advisable. Annual plans with ongoing discounts are worth checking out, as they can reduce costs! This would depend on the insurer. Some insurers allow you to add countries or choose a region. Do note that if the countries you plan to travel to on a single trip don’t belong in the same region, you must purchase two travel insurance plans. So, if you’re planning to travel to multiple countries outside the same region in a single trip, pick insurers that allow you to add multiple countries.