When Should I Buy Travel Insurance?

Last updated on 02/19/2021

Link to Receive Travel Insurance Quote

A common question we are asked is, “When should I buy travel insurance?” Our customers know a plan is important but aren’t sure of the “travel insurance sweet spot”. Do they purchase before a trip is booked? The same day it's scheduled? After the trip is paid off? Before or after they depart?

There are only three "rules" about when to buy a travel insurance plan:

  1. After your first trip payment is made. If you want to purchase a comprehensive plan to cover trip cancellation, we recommend you do it after making at least one payment towards your trip, but some plans require you to have already put money down. You will want to have a good grasp of your total expected trip cost. This will allow you to get the most accurate quote for the right travel insurance plan.
  2. As close to that first payment as possible. If you need coverage for a pre-existing medical condition or are interested in optional Cancel for Any Reason coverage, you should be aware that both of these have time-sensitive eligibility requirements tied to your initial trip payment (among other requirements). In other words, once you’ve paid for a part of the trip (whether it’s airfare, accommodations or a down payment for a cruise) you have a limited amount of time to buy a plan to access these benefits.
  3. Prior to when the plan is needed. You must purchase travel insurance coverage before it is needed. Some travel medical plans are available for purchase after you have departed, but comprehensive plans that include medical coverage must be purchased before departing. However, you can’t buy any medical coverage once you recognize a need for medical attention. The same applies to all travel insurance coverage. Once you recognize the need, it is too late to protect your trip.

So, in reviewing the three rules, you may still be a little confused on that “travel insurance sweet spot.” We tell travelers to prepare early. As soon as you book and make an initial payment on your trip, start comparing travel insurance plans.

While some plans only offering post-departure benefits can be purchased last minute (single-trip travel medical, evacuation memberships or Accidental Death & Dismemberment plans), we advise not to wait when considering plans with pre-departure benefits (comprehensive plans and travel visa plans).

Travel Insurance Quote Link


Only a few travel insurance companies on InsureMyTrip offer plans that cover medical emergencies and evacuation as well as cancellation, delay, and baggage. Some companies offer cancellation-only plans as well. All plans available on InsureMyTrip must be purchased before you leave Canada, you cannot purchase any of these plans once you have departed. Importantly, you cannot purchase coverage for only a portion of your trip; you must fully insure it. If you do not, then the plan would be considered invalid and not provide coverage.