Pedaling Your Way Through Travel Insurance (Revised March, 2022)

Travel insurance is often a blind purchase.  You can buy it from your tour vendor, or from your airline, or from the results of an online Google search.  But none of these methods really educate you about what you are buying.  Most of the time, the only thing you really know about your policy is what it costs.

Given the importance of travel insurance to people who cycle, and especially to people who cycle outside the United States, I think more information is essential.  Hence, this article.


  • If you are on Medicare, medical expenses incurred outside the United States are not covered.  For trips outside the USA, you need medical coverage through a travel insurance policy.
  • Once you have made your first payment for your trip, don’t wait to purchase travel insurance.  As I explain below, failure to promptly purchase coverage will cause your insurance carrier to deny coverage for treatment of medical conditions that preexisted your trip.
  • Don’t regard travel insurance as an afterthough. Handle everythinig as a package. When you are ready to pay a deposit to your tour vendor, have a travel policy picked out and be ready to pay the premium at the same time.
  • Your tour vendor, or your airline, may offer to sell you travel insurance in addition to tour services or airfare.  Think twice before accepting those offers; you can almost certainly do better in the independent private market.

With this in mind, I address the title of this article: pedaling your way through travel insurance.  Exactly what does your insurance cover?  What exclusions apply?  How can you compare competitive travel insurance policies?

Comparing Different Travel Insurance Offerings

Answer: use a service that gives you this information.  I have a lot of experience with .

Squaremouth is an online travel insurance broker with a powerful search engine and an effective way of displaying search results.  The Squaremouth display allows you to search for competitive travel insurance policies and to compare them side-by-side.  Not only the prices for the various policies, but also the features of the policies and an explanation of those features, on an individual feature-by-feature basis.

Here is an example of why feature-by-feature comparison is important.  I have recommended not to wait to purchase travel insurance after you have made your first payment.  This is because all travel insurance policies exclude coverage for a cancellation caused by a medical condition existing within a “lookback period” of X months before your departure.  (The “lookback period” varies from carrier to carrier; Squaremouthtells you what X is for each policy under consideration.)  If for example the exclusion applied, you were treated for asthma onemonth before departure, and you needed to cancel your trip because of an acute asthma attack just before departure, the insurance carrier would deny the claim.  BUT … in all cases, the exclusion can be waived, so that the policy will cover such cancellations.  How?  By purchasing the policy within X days after you make the first payment on the trip.  But, what is X?  It varies from carrier to carrier.  Squaremouth gives it to you for each policy you are looking at.

Most people don’t know about these technicalities, and if you are entirely healthy they may not matter.  But if you have potentially problematic medical conditions, these technicalities matter very much and you need to make sure you purchase an insurance policy before its purchase-by date. And unless you use Squaremouth or a service like it, you may not know what that date is.

Another critical feature of a travel insurance policy is whether its emergency medical coverage is “primary” or “secondary”.  This matters because “secondary” coverage only obliges the carrier to pay what your primary insurance carrier doesn’t.  I personally will not purchase a policy in which medical coverage is “secondary”, but you may decide otherwise.  Regardless which flavor of coverage you elect, you need to know what you are purchasing.  Here, too, if you use Squaremouth, you will know this.  If you don’t, this provision may not be brought to your attention.

CAUTION: watch out for insurance comparison sites that exclude details from search results.  For example, when this article was originally written in January of 2019, I ran a search on .  The search pulled up a number of hits and I elected to compare three of them.  Each policy was said to provide emergency medical benefits of “$X per person ($0deductible)”, with X = $50,000 in one instance and $100,000 in the other two.  From this, it would seem that these policies were very similar, differing only in the limit of coverage, but nothing could be more inaccurate.  Only had you actually clicked on the quoted language would you have learned that the policy with the $50,000 limit offers “secondary” coverage while the other two offer “primary” coverage.  Furthermore, one of the $100,000 limit policies excludes coverage for medical services if the injury results from “Extreme Sports”, which is “an athletic pursuit that involves a high degree of danger or risk”.  Query whether riding your bike is “an athletic pursuit that involves a high degree of danger or risk” ….

Covid-19 and the Cancel For Any Reason Upgrade:

Coverage issues arising from the Covid-19 pandemic are complex and must be considered if you plan to cycle anywhere in the Developing Nations, South America, Africa, or indeed any other place where Covid-19 is rearing its ugly head.  I strongly urge you to consult Squaremouth’s detailed discussion of these issues before paying a deposit to your tour vendor.  As of this writing, this discussion appears at .

This discussion also covers the optional-at-extra-cost “Cancel For Any Reason” feature.  Read this discussion!


Squaremouth offers to help you resolve claim disputes between you and your insurance carrier.  I have not used them for this, but you need to know that if you elect to purchase a TinLeginsurance policy through Squaremouth, this offer may be of questionable value.  This is because Squaremouth owns the TinLeg insurance company.

If you are booking a trip far in advance and you are not precisely sure about your departure date, your return date, or both, most carriers will give you approximately a week’s worth of wiggle room on each of these dates – but only if you give them advance notice.  You must actually get through to the carrier in advance of your departure to advise the carrier about your date change(s).  If you don’t, your claim may be denied.

I welcome your comments and will periodically update this article.  Feel free to contact me at .

Mark Jay

Rev. 4.0, 2022-03