Annual vs Single Trip Travel Insurance: Which Policy Saves You More Money and Hassle?

Choosing between single or annual travel insurance depends on your travel frequency and style. Consider your plans carefully to select the policy that best suits your needs and budget, whether you're planning a quick getaway or a longer adventure abroad.

»MORE: Best Travel Insurance

Single trip travel insurance covers you for one specific journey. It’s a simple, no-frills policy that kicks in the moment you leave home and ends when you return. Think of it as a “pay as you go” option — you only buy what you need, when you need it.

It’s especially handy if you don’t travel often or if you’re going on a once-a-year holiday with your family. For example, if you’re flying to Japan for a 10-day ski trip, a single trip plan ensures you’re protected for that exact period — from medical emergencies to lost baggage and flight delays. The coverage is straightforward, and you don’t have to worry about paying for a year-long policy you won’t fully use.

When should you choose single-trip travel insurance?

You should consider a single trip plan if:

• You only travel occasionally. For instance, a short weekend getaway to Bali or a once-in-a-lifetime Europe tour.
  
  

• You want a budget-friendly option. Prices typically range from about S$12 to S$120 per trip, depending on destination and duration.
  
  

• You’re planning longer trips. Some annual plans limit the number of days per trip (often 30 days), so a single trip policy may work better if you’re away for several weeks or months.
  
  

• You prefer flexibility. You can pick the policy that best suits the destination and activities — say, extra coverage for skiing in Hokkaido or hiking in New Zealand.

Annual travel insurance, sometimes called multi-trip insurance, is designed for frequent flyers. Instead of buying a new policy for each trip, you pay a flat fee once a year and enjoy coverage every time you travel. Whether it’s a quick work trip to Kuala Lumpur, a family holiday in Australia, or a spontaneous weekend in Bangkok, you’re already insured.

This option can be more cost-effective if you take several trips in a year — especially if at least one or two are longer holidays. Instead of buying a fresh policy each time (and filling in the same details again), you only sign up once and stay covered for the whole year. For busy Singaporeans balancing work and family, this saves both money and the last-minute scramble to sort out insurance before every flight.

When should you choose annual travel insurance?

You should consider an annual plan if:

• You travel often. Business trips, regional getaways, or visiting family overseas add up quickly. If you take four or more trips a year, annual plans are usually more cost-effective.
  
  

• You value convenience. One sign-up covers all your travels within the year, so you won’t need to scramble for insurance before each departure.
  
  

• You make last-minute plans. For spontaneous travellers, annual cover ensures you’re protected even if you book a flight the night before.
  
  

• You want consistent coverage. Benefits are standardised across all your trips, so you know exactly what you’re protected for.

Deciding between annual and single trip travel insurance can feel confusing, but breaking it down makes the choice easier. For Singaporean travellers, the right plan often depends on how often you fly, where you’re going, and the kind of trips you usually take.

Travel frequency

This is the biggest factor.

• 1–2 trips a year: A single trip plan is usually enough and keeps costs low.
  
  

• 3–4 trips a year: Do the math. Add up the cost of individual single trip policies versus one annual plan. Depending on your destinations, either option could work out cheaper.
  
  

• 5 or more trips a year: An annual plan almost always saves you money and the hassle of repeated sign-ups. It’s also handy for spontaneous travellers who don’t want to worry about forgetting insurance.

Trip duration

Most annual plans cap the length of each trip at 30 days (some offer up to 60 and 90 days, but those are the exception rather than the norm), which is fine for short getaways or work travel. But if you’re planning a long exchange programme, extended backpacking, or a months-long sabbatical, you’ll likely need a single trip policy that can stretch up to 180 days.

Destinations

Where you travel also shapes the cost.

• Nearby Southeast Asia trips (KL, Bali, Bangkok): Premiums for single trip policies are usually affordable, so annual coverage may not pay off unless you travel often.
  
  

• Further destinations (Japan, Australia, Europe, U.S.): Policies are pricier because of higher medical costs abroad. If you make even a few of these longer trips a year, annual insurance quickly becomes the more cost-effective choice.

Travel style and activities

Your travel habits matter.

• If your trips are mostly sightseeing, shopping, or beach holidays, standard coverage works fine on both annual and single trip plans.
  
  

• But if you love skiing in Hokkaido, diving in Bali, or trekking in Nepal, you’ll need adventure coverage. It can be easier to tailor this for each trip under a single trip plan, though some annual policies also allow you to add these extras.

Budget considerations

Annual plans do cost more upfront, often ranging from S$200–S$1,300 a year, depending on coverage and regions. But the total may actually be lower than buying several single trip policies. A simple way to compare is:

1. List your confirmed trips (including destinations and durations).
   
   

2. Get quotes for single trip policies for each journey.
   
   

3. Compare the total to an annual policy quote.
   
   

4. Factor in promotions (insurers sometimes run seasonal deals).

Calculating the break-even point

The break-even point is where the total cost of single trip policies matches or exceeds the cost of an annual plan. For most Singaporeans, this happens after three to four trips a year if at least one or two are longer holidays. If your travel pattern is more regional weekend getaways, you may need six or more short trips before an annual plan becomes the cheaper option.

Hidden costs and potential savings

Don’t just look at the base premium. Other things can affect your final bill:

• Policy changes or cancellations: Single trip policies may charge admin fees if you need to amend details or shift dates.
  
  

• Last-minute purchases: Buying insurance just before departure can cost more, and it’s easy to forget.
  
  

• Annual convenience: With a year-long plan, you’re always covered without extra charges, which is especially helpful for spontaneous or work-related trips.
  
  

Over time, these small costs and conveniences can add up — making an annual plan worth more than the headline price suggests.

Single trip policies give you protection for the exact duration of one journey, often up to 30 or even 180 days depending on the insurer. Annual travel insurance, on the other hand, covers you for multiple trips within a year, though each trip is usually capped at 30 days. While some premium policies offer extensions up to 60 or 90 days, this is less common and worth confirming before you buy. This 30-day limit is fine for short getaways or work travel.

If you’re a frequent flyer, whether it’s for work, family visits, or spontaneous getaways, an annual plan offers convenience and may save you money in the long run. But if you only take the occasional holiday, a single trip policy is usually the more economical choice.

The key is to match your insurance to your travel habits. Think about how often you fly, how long you’ll be away, and the types of trips you usually take. By weighing these factors, you’ll know whether an annual or single trip plan fits your lifestyle better — and you’ll enjoy peace of mind knowing you’re covered every time you travel.