Last week we found ourselves with a cancelled flight home due to a snowstorm. It required an extra night in our destination, needing to extend our rental car reservation and with other travel expenses. I found myself thinking “I should have bought travel insurance.” But it was a short trip and I never even asked myself before the trip “Should I buy travel Insurance?” Here are some factors to consider when answering that question:
Amount of Time You’ll Be Gone
The longer you’ll be gone the more likely it is that you’ll encounter some type of challenge or problem that would require insurance. For trips of a week or more I would definitely consider buying travel insurance for your trip. But even for weekend trips to a different country or a dangerous (or snowy) city, it might be worth it the added cost. If you’re going on an around-the world-trip for a year – you should not even be asking yourself this question – just jump to the where to buy travel insurance section or to backpackers travel insurance.
Where You’re Traveling To
I always buy travel insurance when I plan an international trip. Why? Not because traveling oversees is necessarily more dangerous, but because I would prefer to have more comforts and reassurances if something did go wrong. Also, the costs if something happened (from medical emergencies to needing an early flight back home) are exceptionally high. Even if you’re going somewhere in country – if it’s an expensive trip or a family vacation it is likely worth it to buy travel insurance.
If You Have Special Medical Needs
If you have any sort of medical needs you should consider travel medical insurance plans specifically. While the cost of medical care abroad may be cheaper, emergency medical evacuations are expensive, and more importantly, having insurance will make you feel better and relieve stress related to finances in cases of emergency.

The Refundability of Your Trip
Is part of your trip non refundable if you cancelled unexpectedly? Your airline tickets most likely are not refundable. Hotel reservations and car rental reservations are likely the only things that you can cancel with just 24 or 48 hours notice. Cruises (see note below) also require buying travel insurance. Consider whether or not your trip is refundable to help you decide if I should buy travel insurance.
The Cost of Your Trip
The more your trip costs the more you have to lose if it got cancelled or interrupted in anyway. Say, for example, that you paid $9,000 for a Galapagos Cruise, then due to weather delays you get there two days late. You have to stay in a hotel for extra nights and pay the extra cost of meeting the cruise at the next destination point. If your cruise was only tens days you’ve missed out on twenty percent of the trip.
Your Ability to Pay Unexpected Costs
If the trip you’re planning is a once in a lifetime trip that you’ve saved money for for a long time – or you’re on a fixed income and couldn’t afford the added expense of an additional night or two at a hotel or a cancelled cruise, then you should buy travel insurance. The added security in case something goes awry is well worth it.
Are You Going on a Cruise?
If you are going on a cruise, buy travel insurance. I have heard countless stories of people having to fight cruise lines for money back due to an unforeseen circumstance. Had they purchased travel insurance they would have had a much easier time.
Where to Buy Travel Insurance Online
Most likely if you are asking yourself – should I buy travel insurance – the answer is probably “yes.” So where should you buy travel insurance online? We did a post about comparing the cheapest travel insurance and found that the best places are either from World Nomads or Squaremouth. World Nomads was cheaper in 2 out of 3 of our scenarios. It is easy to run comparisons on these two sites and determine what is cheaper. (We usually choose World Nomads Travel insurance – you can read our full World Nomads Review.)
Disclaimer: This post may contain affiliate links to World Nomads and Squaremouth. We recommend both of the sites regardless of the fact that we may receive compensation if you book with them through our links.
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Insurance is one of those things that most people hate to spend money on. You rarely have to use it, but when you do you’re glad you got it. If you don’t have to use it, it typically is a forgotten expense after you pay that original credit card bill.
For me, the decision to get travel insurance basically revolves around your statement “The more your trip costs the more you have to lose…” and I act accordingly. I’ve never purchased it for a domestic trip and only a couple times for longer international journeys. Good recap on the topic, Elizabeth.
exactly my thoughts today… due to lack of funds i might not buy one but still thinking about it since i’ll be gone for a few months… thanks for listing everything that needs to be considered…