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Travel insurance for the year-end school holidays with the kids

Planning a family trip for the November to December school holidays? When to buy, family plans, single trip vs annual, and what to check before flying.

15 Oct 2026 · 6 min read

Woman and child walking on the shore
Photo by p - on Unsplash

TL;DR

  • The year-end school holidays run from 21 November to 31 December 2026, so many families are booking flights now.
  • Buy travel insurance when you book, not the night before you fly. Trip cancellation cover only helps if the policy is already in place.
  • A family plan for two adults and their children usually costs less than separate plans. Not every insurer sells one, though.
  • If your family travels more than about three weeks a year in total, an annual plan usually costs less than buying single trips.
  • Long trips over Christmas and the New Year need a plan whose trip length fits your dates.

Is it too early to buy travel insurance in October?

No. If your flights are already booked, October is a sensible time. Trip cancellation cover starts the day you buy the policy. So if your child falls ill or a family member dies before you leave, a plan bought early can pay back what you can't recover. A plan bought the day before you fly gives you none of that time.

It depends on whether you've actually paid for anything yet. If you're still deciding between Bali and Hokkaido, there's nothing to cancel. Once the tickets and hotel are paid for, that's the point to get cover.

What does trip cancellation pay for if our plans change?

It pays back costs you can't get refunded, but only if you cancel for a reason the policy covers. Illness and a death in the family are the usual examples. Cutting a trip short for a covered reason is part of the same cover. Simply changing your mind is a different matter, so read the list of covered reasons before you count on it.

What it depends on is the plan level and how much you've prepaid. Most insurers sell two to four levels, and higher levels pay more for cancellation. If you've paid a lot upfront for a long-haul trip, check the cancellation limit against what you'd lose. Limits differ between plans, so compare them on the travel quote page.

Do family plans cover our kids?

Yes. A family plan is built for two adults and their children travelling together. It usually costs less than buying a separate plan for each person. Insurers also charge less for children than for adults. For families, we price plans from the insurers that offer a family plan, so the list can be shorter than it is for one adult.

What it depends on is who is actually going. Bringing the grandparents along? Insurers charge more for older travellers, and some stop covering travellers above 75, 80 or 85. The insurer confirms each person's age when you apply. How a plan defines a child also differs between plans, so check it if you have teenagers.

Single trip or annual plan for a family that travels a lot?

If your family is away for more than about three weeks a year in total, an annual plan usually costs less. A single-trip plan covers one journey, from the day you leave Singapore until you come home. An annual plan covers every trip in the year, each up to a set length, often 90 days. For annual cover you pick a region (ASEAN, Asia Pacific or worldwide) instead of countries. Pick the one that covers the furthest place you expect to go.

To give you a feel, here are today's prices for one adult aged 18 to 59. These are examples, not what you will pay:

  • Long weekend in Malaysia: 13 insurers, from about S$11 to about S$86 (see prices)
  • One week in Thailand: from about S$17 to about S$146 (see prices)
  • Two weeks in Japan: from about S$36 to about S$270 (see prices)
  • A year of trips in Asia: from about S$190 to about S$905 (see prices)

What it depends on is your real calendar for the year. Count this December, the March and June holidays and any long weekends away. Add up what single trips would cost, then set that against the annual price for the region you need.

We're away over Christmas and New Year. Is a long trip a problem?

Usually not, but check the maximum trip length. One trip means one departure from Singapore and one return. Most insurers here cover a single trip of up to 90 or 182 days. On an annual plan, each trip has its own limit, often 90 days. Single-trip prices also rise with the number of days.

Where you go matters too. Trips within South East Asia cost the least. Asia Pacific costs more, and worldwide cover costs the most because it includes the United States. Treatment in Japan, Europe or the US can cost tens of thousands of dollars, so medical cover matters most here. For a sense of scale, three weeks in Europe for one adult today runs from about S$68 to about S$558 (see prices). You can also check Japan, Australia, Europe or the USA.

What should we check before flying?

The exclusions, because those are what catch people out. The main ones:

  • Pre-existing medical conditions are not covered unless you declare them and the insurer accepts them. A few plans cover them, mostly on shorter single trips, and there's a filter for them on the results page.
  • Places the Ministry of Foreign Affairs (MFA) advises against are not covered. Check the MFA's travel advice for your destination before you go.
  • Losses while under the influence of alcohol or drugs are excluded.
  • Belongings left unattended in a public place are not covered. Think of the bag left on a chair while you queue for food.

Most plans now include COVID-19 cover for medical bills and cancellation. Prices on this site include it unless you choose "Not needed" in the filters.

What it depends on is your family's health. If anyone has an ongoing condition, declare it when you apply and see whether the insurer accepts it.

What if something goes wrong while we're away?

This is what the policy is for. Travel insurance covers medical treatment and hospital stays overseas, emergency evacuation and repatriation, and lost or damaged baggage. It also covers travel delays and missed connections. Save your policy number and the insurer's emergency contact on your phone before you leave.

What the insurer needs from you differs between plans. Our Claims page explains how claiming generally works.

What to do next

  • Put in your destination, dates and who is travelling on the travel quote page, and compare family and annual options.
  • Browse example prices for your destination on the prices page, such as Thailand, Taiwan or South Korea.
  • Before you pay on the insurer's site, read the covered reasons for cancellation and the exclusions list.