The only travel insurance I regularly invest in is car rental insurance. Even then, I’m pretty happy-go-lucky with the policy I choose.
Videos by TravelAwaits
On one hand, travel insurance is theoretically more necessary now than ever before. Americans face long delays at the airport and hefty airfare prices, but have little to no recourse when delays cause missed connections. There’s also the reality that inclement weather, from heat waves to hurricanes, will continue to put vacations at risk.
On the other hand, travel insurance policies come with tons of fine print and only protect you in case of disaster. You might end up paying a lot for basic coverage… and still might not be refunded a dime if the ‘right’ disaster doesn’t throw off your trip.
Here’s my take: I seek out low-cost and low-risk trips, so travel insurance hasn’t really been on my radar. But here’s the truth: It probably will be in the coming years if there aren’t some positive changes in the travel industry. Climate change is another factor at play, as inclement weather is expected to become more widespread in the coming years.
So, let’s cover the signs that you should look for a travel insurance policy for your upcoming trip. I’ll bring up which types of policies are most relevant in each case, too. Again, you should always read the fine print before signing off on a new policy. Unless you pay for a CFAR (Cancel for Any Reason) policy, you’re going to have partial coverage.
7 signs you need travel insurance for your upcoming trip
Sign #1: You’re paying a lot for the experience
If you’re paying for luxury, you should be forking over a little more for a solid, comprehensive travel policy. Usually, these elements go hand-in-hand. What I mean is that if you put together a trip with a luxury travel agent, they’re going to have an insurance policy in mind for you.
This is also the case with modular luxury trips where you organize everything—from hotels to tours to fine dining. You are usually offered travel insurance for a fee when booking these experiences, which lets you cancel or reschedule. Or you can purchase an independent travel protection policy from a company like Berkshire Hathaway, for example.
Sign #2: You’re heading out into the boonies (think: adventure trips)
If you’re heading out on an adventure safari or multi-day trek, go for travel insurance. Once again, the company organizing your intrepid adventure should have a list of policies for you to choose from—especially considering many safaris, treks, and similar experiences are in the luxury sector.
But you might want to look into travel insurance even if you aren’t adventuring with an upscale travel company. Let’s say you’re going to Colombia’s Ciudad Perdida, which requires a multi-day hike in the remote jungle. I recommend checking out an independent travel insurance policy that covers things like medical evacuation.
Sign #3: You have health concerns
Speaking of medical evacuations, you might want to consider travel insurance if you have ongoing health concerns or chronic issues. Some policies make it easy for you to receive world-class coverage in your destination, while others cover full-on helicopter evacuations that will have you on a flight home as soon as humanly possible.
Usually, medical policies have a few different tiers that come with different limits and deductibles—be sure to read each policy closely. The language gets very complex when medical topics are involved.
Sign #4: Inclement weather is a strong possibility (think: seasonal travel)
Like I mentioned up-top, inclement weather is becoming more of an occurrence around the world. Europe has been plagued with wildfires this summer, while powerful tropical storms have popped up increasingly around the Caribbean. Some travel insurance policies even cover occurrences like heavy rain and heat waves.
Most of these concerns are seasonal, meaning you can avoid heat waves by traveling in winter and tropical storms by staying inland. However, you’ll often find high-value deals for traveling in the off-season. If you want to take advantage, you might consider looking into weather-based policies that will cover big-ticket items, like a cruise during hurricane season.
Sign #5: There are a lot of moving pieces
The longer the trip, the more opportunities for something to go wrong. If you’re heading out on a multi-city or multi-week trip, look into travel insurance. Policies can help you rebook flights, hotels, and more in case you get delayed and can’t reach the next leg of your trip right away.
Usually, in these cases, a more comprehensive CFAR policy is the way to go. That way, you don’t have to worry about figuring out what’s covered and what isn’t when looking at car rentals, hotels, flights, trains, tours, and so on.
Sign #6: You’re not packing light
Once again, this goes hand-in-hand with multi-stop trips or longer trips—you probably won’t be packing light. If you’re bringing multiple checked suitcases, go for travel insurance that covers lost luggage. That’s doubly true if you’ve invested in a nicer setup like, say, a Carl Friedrik checked luggage.
You can look for travel insurance policies that cover your luggage in two ways. First, policies that compensate you for lost, stolen, or damaged items. As in, the airline loses your bag forever. Second, policies that cover essentials while you’re waiting for your bag to make it to your final destination. In this case, your bag isn’t lost—it’s just delayed.
Sign #7: There’s a chance you can’t make the trip
Why would you plan a trip that you aren’t sure you can make? Off the top of my head, I can think of two personal examples. First, having an older dog who isn’t actively sick but is more or less flirting with the reaper. You never know. Second, the possibility of landing a new job, which happens to freelancers like me sometimes.
It’s not good form to plan trips that you aren’t sure you can make, but if you find yourself in this position, look for travel insurance. I recommend finding a CFAR policy (again, that Cancel for Any Reason) that offers wide coverage because there’s no policy that’s going to pay out when you miss a cruise to attend a dog funeral. (Unfortunately.)