If you’re planning a months-long sabbatical, a gap year abroad, or even frequent overseas trips within a year, it may be time to look beyond standard travel insurance. Instead, consider long-term travel insurance that protects you from unexpected costs over extended periods — whether it’s medical emergencies, flight disruptions, or lost belongings.

Long-term travel insurance is designed to keep you covered across multiple trips or an extended stay overseas. From digital nomads to students, retirees, and business travellers, these policies can be a valuable safety net. 

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Here's our list of the best long-term travel insurance plans:

• MSIG Standard Plan

• SingLife Travel Plus Plan

• Great Eastern TravelSmart Premier Classic

• Zurich Travel Protect

• Singtel Travel Protect – Economy

>> Learn more: The best travel insurance companies

When evaluating the best long-term travel insurance options for Singapore residents, we focused on features that matter most to extended or frequent travellers — especially those with flexible schedules or long overseas stints.

1. Coverage scope: We looked for policies that included comprehensive coverage, such as emergency medical treatment (including COVID-19), trip cancellations or delays, and lost or stolen luggage. These are critical for anyone travelling far from home for months at a time — where the risk of medical emergencies or logistical hiccups naturally increases.

2. Ease of purchase: We prioritised providers that offered a seamless application experience. This includes intuitive online quote tools, fast approvals, and access to 24/7 emergency hotlines. After all, a great policy means little if it's difficult to apply for.

3. Customisation: Flexibility is key for long-term travellers. We gave higher marks to plans that allow you to tailor coverage based on your travel style, such as optional add-ons for high-risk sports, cruise trips, or expensive electronics. We also checked whether pre-existing conditions could be covered and if the plan allows for extensions or changes mid-way. The more adaptable the policy, the better it can meet your real-world needs.

By focusing on these criteria, we ensured our picks for extended-stay travel insurance strike the right balance between value, protection, and convenience — making them ideal for Singaporeans seeking peace of mind while abroad.

>> Learn more: 10 tips for buying the right travel insurance

Depending on your travel habits, some policies will work better than others. To make the best decision, consider how long you'll be away, how often you travel each year, and whether you need flexibility for pre-existing conditions or adventure activities.

Here’s a comparison of some of the best insurers in Singapore offering travel insurance for long stays or multiple trips:

>> Learn more: Essential travel resources to maximise your benefits

Let’s zoom in on each provider to better understand their strengths when it comes to extended-stay travel insurance:

Why MSIG Travel Insurance stands out:

• Comprehensive medical and travel inconvenience coverage

• COVID-19 protection including quarantine, cancellation, and hospitalisation

• Flexible add-ons for adventurous activities and high-risk scenarios

The MSIG Standard Plan costs approximately S$21.82 after promotion, offering one of the best value-for-money long-term coverage options in Singapore — with benefits like S$25,000 medical expenses, S$5,000 trip cancellation, and S$3,000 baggage loss.

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Why Singlife Travel Insurance Plus stands out:

• Generous coverage for medical expenses and trip cancellations

• Covers trip changes for any reason — even pre-existing conditions

• Higher benefit limits for frequent or family travellers

Singlife Travel Plus plan strikes the perfect balance between value and protection, offering S$2,000,000 evacuation coverage, S$15,000 for trip cancellations, and S$5,000 for lost baggage — making it a smart choice for repeat travellers and families alike.

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Why Great Eastern TravelSmart Classic stand out:

• Comprehensive trip cancellation coverage of up to S$10,000

• Generous baggage protection and COVID-19 medical benefits

• Built-in adventure activity cover at no extra cost

For our test, the Great Eastern TravelSmart Premier Classic plan cost just S$28.05 after promotion, making it a solid mid-tier option. With S$15,000 in medical expenses, S$5,000 baggage loss, and quarantine allowances, it’s great for travellers who want more coverage without going full premium.

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Why FWD Premium Travel stands out:

• Simple online purchase process

• Comprehensive benefits at affordable rates

• Plans tailored for all travel styles

FWD’s Premium plan costs S$19.87, which is among the lowest in its category. It is built for modern travellers who want flexibility, value, and peace of mind—whether you're flying, road-tripping, or setting sail on a cruise.

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Why Singtel Travel Protect Economy stands out:

• Enjoy trip cancellation coverage up to S$10,000

• Get medical coverage up to S$8,500

• Includes baggage delay (up to S$1,200) and loss of baggage (up to S$5,000)

• Phone Care, Bill Protect, and Data Rescue benefits for Singtel mobile users

This plan is ideal if you want more generous medical and travel inconvenience coverage, plus tech-friendly perks. This plan balances protection and value for long-term stays.

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>> Learn more: Discover promotions and discounts for travel insurance

To sum it up, the choice of long-term travel insurance plan depends largely on your travel style.

For business travellers or frequent holidaymakers taking multiple trips throughout the year, annual plans may be best as they tend to be more cost-efficient and provide convenience and flexibility for those with fluid itineraries. Single extended trip plans are ideal for travellers with a fixed schedule who need uninterrupted coverage for the entire duration of their trip, like if you were taking a gap year, sabbatical, or extended work placement abroad.

When selecting your plan, it’s also important to consider whether it offers coverage for pre-existing medical conditions. Not all long-term travel insurance policies include this by default, and if you have a known health condition, opting for a plan that covers ongoing treatment or unexpected flare-ups can save you from hefty out-of-pocket costs. Look out for insurers that allow add-ons or customisation to ensure you’re fully protected throughout your journey.

Looking to earn more from your next adventure? The right travel credit card can help you rack up miles, enjoy airport perks, and stretch your travel budget further. Here are some of the best travel credit cards in Singapore for 2025, depending on what matters most to you:

• Best for miles: Citi PremierMiles Card

• Best for cashback with no minimum monthly spending: Standard Chartered Smart Credit Card

• Best for overall cashback: UOB One Card

• Best cashback for shopping and dining: HSBC Live+ Credit Card

• Best for frequent flyers: HSBC TravelOne Credit Card

• Best for fuel discounts: Citi Cash Back+ Card