Going on a Long Overseas Trip? Be Sure to Buy the Best Long Stay Travel Insurance from Singapore.

Alevin Chan

Alevin Chan

Last updated 06 March, 2024

Travel insurance is arguably more important for those spending longer periods overseas. Get the best long stay travel insurance from Singapore.

Best Travel Insurance in Singapore

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Let’s get one thing out of the way: You absolutely need the best travel insurance in Singapore if you’re going on a long-term overseas trip.

This is because your Medishield Life and/or Medishield IP only cover you for hospitalisation and medical treatment when you’re in Singapore. Which means, the longer you are away from home, the more you’re running around without medical insurance coverage.

Also, if you’re taking a 6-month sabbatical to, uhm, run with the horses or something, the chances of you breaking a foot is much higher than if you were simply sitting at your desk bound job.

So now that we’ve established that you’re going to need travel insurance for that long-awaited odyssey around the world, let’s take a closer look at your options.


Table of Contents

What is Long Stay Annual Travel Insurance?

Long-term travel insurance is designed for those taking trips that last a long duration, typically several months to a few years. They are suitable for parties such as digital nomads, gap-year backpackers, overseas exchange students, those wishing to work overseas for a year or two, etc.

Long-term travel insurance is highly similar to conventional travel insurance plans. They usually offer overseas medical cover, including benefits for emergency evacuation, personal accident and such; travel curtailment cover, including for missed flights or trip cancellation; and personal belongings benefits, covering delayed luggage, and theft or damage of your items, etc.

One core difference is that long-term travel insurance is less restrictive than some travel insurance policies may be, in regards to the maximum duration of your trip. 

For instance, you may be able to insure a trip that lasts 24 months via a long-term travel insurance plan, whereas most conventional travel insurance plans only allow a maximum coverage of 6 months.

Why Choose Long Term Travel Insurance Plans?

Opting for long-term travel insurance plans is a strategic decision for those embarking on extended stays  or journeys (such as students and expatriates). 

These plans understand the nuances of long-term travel and offer a comprehensive safety net, providing peace of mind over long-periods. 

For example, a key benefit of long-term travel insurance is extended coverage for overseas medical expenses, which is vital when you're far from home and potentially exposed to different health risks. 

Moreover, these plans often come with flexibility to cover multiple destinations, making them perfect for globetrotters exploring various countries in one trip.

From flight delay insurance to support during travel disruptions, these policies ensure you're well-protected on your adventures.

What Does Long Stay Travel Insurance Coverage from Singapore Include?

Long stay travel insurance coverage from Singapore is meticulously designed to cater to the needs of travellers engaging in prolonged trips.

This coverage typically includes a broad spectrum of benefits, ensuring travellers are comprehensively protected against unforeseen events. 

Key inclusions are medical and emergency services abroad, which cover hospitalisation, treatments, and even medical evacuations if necessary. 

Additionally, policies provide for travel inconveniences, such as trip cancellations, delays, and baggage issues, ensuring that the financial implications of these disruptions are minimised.

What Does Long Stay Travel Insurance Coverage from Singapore Not Include?

However, it's crucial to acknowledge the limitations of long stay travel insurance as well. 

Typical exclusions encompass:

  • Pre-existing medical conditions (but there are travel insurance for pre-existing conditions)
  • High-risk activities not specified in the policy (you might need adventure travel insurance instead).
  • Costs and fees related to traveller or employee replacements.
  • Activities that go against government rules/regulations/prohibitions.
  • Actions leading to or related to illegal activities.

Understanding these boundaries is essential to ensure that your travel insurance meets your expectations and requirements.

What Happens if You Have Pre-existing Medical Conditions?

For travellers with pre-existing medical conditions, navigating the world of long stay travel insurance requires attention to detail. 

While some insurers may offer coverage, it often comes with stipulations or additional premiums. It's imperative to disclose such conditions during the application process to avoid complications or claim rejections later on.

You can also consider buying specialised travel insurance for pre-existing conditions that’s designed to suit your medical and financial coverage needs.

Does Long-Term Travel Insurance have an Age Limit?

Moreover, potential buyers should be aware that long-term travel insurance may include upper and minimum age restrictions. These limits vary by provider but can influence the availability and cost of your policy. 

Seniors, in particular, should carefully review these terms to find a policy that accommodates their needs, or look at buying the best travel insurance for those over 65 to ensure comprehensive coverage.

Parents bringing their young children abroad for extended stays should also ensure the coverage extends to their young ones, or consider alternative family travel insurance plans to extend your coverage further.

What is the Global Healthcare Insurance Plans (Expat Plans) Type?

Global healthcare insurance  plans (aka expat plans)

Global healthcare insurance plans are simply medical insurance plans that offer coverage no matter where you are in the world.

Coverage is offered on a persistent basis, as long as the policy remains in force. There are no restrictions in terms of duration; you’ll get the same level of coverage whether you’re holidaying in Bangkok for a week, visiting home for a month in Australia, or working at your investment banking job in Singapore for the next five years.

However, there may be restrictions in terms of geographical region (such territories at war), and you may have lower coverage – or even none – in certain countries, such as the U.S.

Nonetheless, global healthcare plans offer convenience and versatility to expatriates or those who find themselves spending a fair amount of time living in different countries.

But on the other hand, such plans do not offer a well-rounded solution to travellers.

This is because global insurance plans mainly cater to healthcare and medical needs. They do not generally cover travel risks, such as travel delays, missed flights, damaged or missing luggage and personal items, etc.

Which Is Better: Annual Travel Insurance Vs. Single Trip Travel Insurance?

Choosing the right travel insurance depends on your travel frequency, trip duration, and specific needs. Annual travel insurance is best for those who travel multiple times a year, offering convenience and potential savings. Single trip insurance is ideal for longer, one-off trips or infrequent travelers, providing tailored coverage for specific trips. 

Understanding the differences between single vs annual trip insurance can help you make an informed decision on which option suits your travel plans best. For a more detailed comparison and to find the best plan for your needs, visit Singsaver's guide on travel insurance.

Feature Annual Travel Insurance Single Trip Travel Insurance
Coverage Duration Covers all trips made within a 12-month period Covers one specific trip, typically up to 180 days
Maximum Trip Length per Coverage Each trip within 12-month period covered for 30 to 90 days, depending on the insurer Can cover trips up to 180 days, ideal for long vacations or stays 
Cost-Effectiveness More cost-effective for travellers planning multiple short trips within a year More economical for one long trip or if travelling infrequently
Convenience Purchase once and travel multiple times without the need to buy insurance for each trip Must be purchased for each trip, which can be cumbersome for frequent travellers
Suitability Ideal for frequent travellers with multiple short trips (e.g., business travellers, weekend getaways) Best for travellers taking a prolonged single trip or those who travel infrequently
Pre-existing Conditions Coverage May offer coverage for pre-existing conditions, but conditions apply and vary by insurer More likely to find specific coverage for pre-existing conditions tailored for the duration of the trip
Flexibility Limited flexibility in terms of trip length coverage; may not suit extended stays  High flexibility, can tailor coverage duration to the exact length of the trip
Implications for Long Trips Not ideal for trips exceeding the maximum covered trip length without additional coverage Better suited for multi-month holidays or long stays in a single destination


And then of course, there’s also good ole travel insurance, which comes in two flavours – single-trip plans and annual plans.

Counterintuitively, it is single-trip plans (and not annual plans) that make for the better choice for multi-month holidays.

This is because most single-trip plans cover you for up to 180 days overseas, even if you travel to several different countries during your trip.

In comparison, annual plans cover all overseas trips taken within a 12-month span, but each individual trip will only be covered for between 30 days to 90 days – depending on your insurer.

What’s the implication of this? Well, let’s say you’re planning to stay at least two months in Japan at one go. Your annual plan only covers each trip for 30 days. If you come to require medical attention on Day 33 of your holiday, your insurer has the right to reject your medical bill claim.

In such a scenario, you’d be better off with a single-trip plan with two months of coverage. Or, you should purchase an additional single-trip plan to cover the second half of your trip.

Additionally, annual travel insurance also tends to have a higher upfront cost, but pays off by having a greater value-for-money compared to buying multiple single-trip plans. To save more on your annual travel insurance you can also check out SingSaver’s annual travel insurance promotions and discounts for the latest deals and offers.

Unconvinced? Our guide to annual travel insurance VS single trip travel insurance might answer your questions.

Which type of travel insurance should long-term travellers choose?

Well, it all boils down to two factors: the length of your trip, and how many trips you’re taking. But generally speaking, conventional travel insurance should adequately serve the needs of most long-term travellers.

If you plan on taking two or more trips, in a year, and don’t expect each trip to last longer than three months each, you may find the best value with an annual travel plan that covers up to 90 days per trip.

Note that your premiums will be affected by the region you travel to, so you should organise your itinerary accordingly to keep costs low.

If, however, you prefer to travel with as little restrictions as possible, getting a single-trip plan will be the most fuss-free option for you. You can purchase the coverage you need, and add on or alter your coverage as you go along.

So for instance, you can start by buying a single-trip plan for two months in Southeast Asia. Then, if you want to continue your holiday for another month in Japan, you can contact your insurer to extend your coverage, or simply purchase a separate travel insurance policy for Japan to cover the next leg of your trip.

One thing to note though is that insurers may impose a limit on the maximum number of days they will cover you within a specific period – such as 180 days out of 365.

This means that you will not be able to purchase a second single-trip policy to continue covering your travels if you’ve already spent more than 180 days overseas, and will have to approach another insurer instead.

As such, if you plan to be overseas for a considerable period of time, and don’t want to deal with multiple travel insurance providers, you might want to look into long-term travel insurance plans. You’ll have less uncertainty about your coverage, and may even be able to achieve some savings.

And as for global healthcare insurance, as explained, that is really more for expatriates or those moving to another country. That, combined with the lack of travel benefits, mean such plans should not be your first choice for long-term travel coverage.

Read these next:

Best Travel Insurance Plans And Promotions In Singapore (2024)
Best Annual Travel Insurance Plans In Singapore (2024)
Travel Insurance Guide: Five Things All Travellers Must Know
Travel Insurance Policies that Cover up to S$3,000 for your Jewellery
Best Travel Insurance for Travellers with Pre-Existing Conditions (2024)

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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