Once flights and hotels are paid for, you suddenly have a lot of money riding on one set of dates. Illness, family emergencies, work issues or storms can derail everything before you ever reach the airport. That’s why the ideal time to buy travel insurance is shortly after booking your first nonrefundable expense, not the week before you fly.

Travel insurance is essentially a safety net: it can reimburse covered losses from cancellations, delays, medical emergencies, lost baggage and more, depending on the policy you choose. The earlier you secure it, the more situations it can actually cover.

Meghan Walch, a travel insurance expert, states, “It is important to know what your travel supplier’s refund policies are, and purchase insurance as soon as possible if you stand to lose a significant amount of money.”

Trip Cancellation Cover

Trip cancellation protection is one of the biggest reasons to buy early. If a covered event forces you to cancel before departure, the insurer can reimburse prepaid, nonrefundable costs such as flights, hotels, tours and excursions.

Imagine booking an overseas trip months ahead, then facing a sudden medical issue in the family. Without coverage, airline tickets and deposits could become very expensive souvenirs. With cancellation protection in place, much of that loss may be recovered. Some plans offer “cancel for any reason” (CFAR) upgrades, which reimburse a portion of costs even when the reason isn’t listed in the standard policy. However, CFAR is typically time-sensitive and must usually be added within roughly a couple of weeks of the first trip payment, depending on the plan.

Pre-Existing Conditions

Travellers with ongoing health issues need to pay close attention to timing. A pre-existing condition usually means any illness or symptom you had or were treated for in a defined period before buying the policy.

Many insurers offer a waiver for those conditions, meaning related claims can still be covered—but only if you purchase the policy soon after your initial trip payment. Miss that window and you may find that any care tied to that condition is excluded, even if the rest of the medical benefits are intact. Buying soon after booking increases the odds that existing health needs are properly protected while you’re away from home.

Free Look Window

Most travel insurance plans include a brief “free look” or review period, often 10 to 15 days after purchase. During this time, you can read the policy thoroughly, ask questions and, if it truly doesn’t fit your needs, cancel for a full refund.

There is a catch: once your trip actually begins, that review period ends. Purchasing soon after booking gives you enough time to compare fine print, make changes or switch plans without pressure.

When It’s Late

Is it ever too late to buy coverage? Not always—but the later you wait, the fewer protections you’ll have. Some insurers sell policies right up to departure or even after you’ve started your trip. These typically focus on post-departure benefits like emergency medical care, evacuation and baggage issues. They usually don’t include trip cancellation, and they won’t cover events that are already known or underway.

If a major storm has already been named and is clearly threatening your destination, for example, a new policy generally won’t pay out for cancelling because that event is no longer “unforeseen.”

Check Existing Coverage

Before buying a separate policy, review benefits you might already have. Some credit cards include limited trip delay, baggage or cancellation protection when you use the card to pay for travel. Homeowners or renters insurance can occasionally provide a small amount of coverage for belongings away from home, though usually not enough to replace full baggage protection. Knowing what’s already in place helps avoid paying twice for the same benefit.

Compare Providers

Once you know your gaps, research dedicated travel insurance providers. Look for companies with strong financial ratings, clear policy wording and responsive customer support. Quote comparison sites can help you view multiple plans side by side, filtering by trip cost, destination, traveler age and desired benefits. Focus on value, not just the cheapest premium—thin coverage is rarely a bargain when plans go wrong.

Match Plan To Trip

Choose coverage based on the trip you’re actually taking. A short domestic visit might only need medical and baggage cover, while a long international holiday may call for higher medical limits, evacuation, and robust cancellation protection. Consider whether you’re carrying expensive equipment, booking non-refundable tours or taking part in higher-risk activities. These details determine whether you need extra baggage limits, sports equipment protection or specific adventure-activity coverage.

Read The Fine Print

Before paying, go through the policy wording carefully. Check maximum limits, deductibles and, most importantly, exclusions. Common carve-outs include some adventure activities, certain medical conditions and situations where you simply change your mind. If something is unclear, contact the insurer during the review period and get written clarification. That extra ten minutes of reading often prevents major disappointment at claim time.

Understand Claims

Knowing how to use the policy is just as important as buying it. Familiarize yourself with the claims process: how quickly you must notify the insurer, what documents are required and how to submit them. If a flight is delayed, a bag goes missing or a medical issue arises, contact the insurer’s assistance line promptly. Keep receipts, booking confirmations, medical reports and any official notices; these serve as the backbone of a successful claim.

Keep Proof Handy

After purchase, store your policy details with your travel documents. Save digital copies on your phone, keep emergency contact numbers accessible and download any mobile app the insurer provides. It’s also wise to leave a copy of the policy information with someone at home. If you’re unable to call, they can contact the insurer on your behalf in an emergency.

Flights And Cancellations

When airlines cancel flights, they generally remain responsible for refunding or rebooking tickets. Travel insurance usually steps in around that, covering non-refundable expenses such as prepaid accommodation or tours if a covered disruption forces you to scrap or cut short the trip. Coverage for airline failure, mechanical issues or extended delays depends heavily on the policy wording, so this section deserves special attention when you compare plans.

Changes And Flexibility

If you must move flights because of a covered reason, such as sudden illness, some policies reimburse change fees and extra transportation costs. When the airline alters your schedule, travel insurance may help with knock-on expenses like additional hotel nights or missed transfers. By contrast, purely voluntary changes—deciding to leave later for convenience—typically fall outside cover, unless you purchased a CFAR upgrade.

Final Thoughts

Yes, you can buy travel insurance after booking your flight—and doing so promptly is one of the smartest financial moves you can make before a trip. Early purchase opens the door to stronger cancellation protection, pre-existing condition waivers and a stress-free review period. With a bit of comparison and careful reading, you can match coverage to your plans and travel with far more confidence. Next time you click “book now,” how soon will you protect that trip with a policy that fits?