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Theoretically, I’m the type of person who shouldn’t buy travel insurance. I’m young and healthy, I have an emergency bank account to help cover unexpected expenses, and I have a large stash of frequent flyer miles I can draw on if I need to fly home in the middle of a trip for problems back home. But despite that, I just bought another year of multi-trip insurance.
Why? Because just last month, I had another flight with major issues leading to unexpected expenses. And I had accidentally let my annual travel insurance lapse, so I was left with the bill. Oops.
Well, I didn’t think I’d be left with the bill: I did indeed file a claim with my “free” travel insurance plan included as a credit card benefit, but it was A) a hassle and B) denied.
But instead of leaving me cynical, it was a good reminder to myself why a good policy is worth its weight in gold.
My Most Recent Travel Insurance Claim
Let me set the stage a little: I was scheduled to fly Los Angeles to Hong Kong to Shanghai to Harbin. (Yes, it’s a rather circuitous way to get there, but I’m a sucker for a good deal). I had a 2.5 hour layover in Hong Kong and 9 hours in Shanghai, both of which seemed more than adequate so I wasn’t particularly worried about what could go wrong.
Turns out I needed to worry.
To make a long story short, my flight left Los Angeles four hours later. I missed my connection in Hong Kong and that cascaded into missing my next connection, too.
Because of the delays, I missed out on a prepaid hotel reservation in Shanghai and had to buy a brand new ticket, last-minute, for the last portion to Harbin to try and salvage my trip (otherwise, I would’ve missed out on the Harbin Ice Festival entirely).
Thankfully, my delays and the denied insurance claim didn’t bankrupt me, but it did put a dent into my travel fund and nobody likes that!
(And while this one was relatively minor, I’ll remind you this is now the 6th claim in 5 years I’ve filed. Either I have bad luck or travel issues are way more common than you think.)
If any of these things sound like something that could happen to you, it’s time to think about travel insurance:
- Your flight is canceled or delayed so you miss a day of your trip (ask me about my 4 day wait in Panama or being stuck in Charlotte, NC)
- You miss a connection, which causes you to rearrange your trip last minute (not just recently in Hong Kong, but stuck in Phoenix once, too!)
- Your baggage is lost or stolen (for me, on a NYC bus, although it was ultimately returned after I spent $100 on replacement clothing, deoderant, etc)
- You lose your wallet with money and credit cards (never me, but my sister and my dad)
- You get sick and need medical attention (my husband last month in Puerto Rico; my mom’s emergency dental work in Poland)
- Your family member is hospitalized back home and you need to return immediately (hasn’t happened to me exactly, but I did have to travel for a family member literally the day after I got home from Bogota and it could’ve just as easily been while I was on the trip)
Why Multi-Trip Insurance, Specifically, is the Way to Go
Okay, so you get it. Reputable travel insurance can reimburse you, whether it’s $190 in unexpected expenses or $500 in lost luggage or $10,000 in emergency medical bills.
But why do I prefer multi-trip insurance? And why should you?
First, for a frequent traveler, annual travel insurance saves you time compared to buying a new policy on every trip. I’m not talking about the five minutes you save getting a quote and entering a credit card number — obviously that’s no big deal. I’m talking about how when you purchase a policy, you need to read through the inclusions, exclusions, restrictions, and other fine print. That takes time to read and digest and it’s easier to do once a year than for each and every separate policy.
Second, it’s cheaper than buying multiple policies. For me, the multi-trip quotes I get are about 2.5x the time of a single trip. If you travel 3 or more times per year, you’re money ahead (plus you’ll be protected on the little trips you otherwise might overlook, like flying to a friend’s wedding for a weekend). I realize not everyone takes three trips a year, but if you do, this is definitely the way to go. Obviously travel insurance is the least interesting thing you can buy for vacation, so if you save a little, you’ll have more left over for the fun stuff.
How Much is Travel Insurance?
Even on multi-trip travel policies, there are a lot of factors here, including your age, the average cost of your trips, and what state you live in.
Here’s the actual cost for my husband and I (two travelers) for a one-year policy with trips costing up to $5,000.
An Unwritten Upside to Annual Travel Insurance
The other major, unwritten benefit to choosing multi-trip travel insurance is that you’ll learn the ins and outs of how to quickly and successfully file a claim. I hope you never have to file one, but realistically if you’re traveling that often, it’s bound to happen.
If you get a different policy every time, you have to familiarize yourself with maximum reimbursements and how long you have to start a claim or file documentation thereafter.
Here’s the thing: now that I’ve filed several claims with the same company, I know exactly what I need for a successful claim. It’s really easy to get a flight delay certificate when you’re already at the airport and staff is familiar with your specific incident. Same thing for doctor’s notes (and presumably police reports). The same certificate is time-consuming to chase down by phone weeks later. Scanning, naming, and uploading my files takes me less than 10 minutes now, but my first claim probably took hours to gather the right documents and talk to the right people.
Travel insurance is far more valuable if a claim is easy to file and likely to be paid out.
And that right there is why I don’t just buy any travel insurance but choose multi-trip insurance specifically.
Tips for Buying Travel Insurance for Multiple Trips
There’s already a lot to look over when buying travel insurance, but there are a few extras if you choose an annual policy:
1. Even though you can take as many trips as you want, there’s usually a maximum duration per trip (often 30 days). Most people won’t have an issue with that; if you do, shop around or look into single-trip insurance which can be any length of time, priced accordingly.
2. Most annual policies focus on travel health insurance or emergency treatment abroad, and may have an annual cap on the total dollar amount you can claim in a year. So, if you have to make a last-minute $10,000 trip cancellation claim because of a death in the family, you may not be able to make that type of claim again later that year. I’ll state the obvious and say if you made a major claim like that, study your insurance limits so you know whether or not you need to buy a separate policy for the rest of the year.
How to Buy Multi Trip Insurance Policies
Almost all companies have the option for annual multi trip insurance on their quote tool (look for either “multi-trip” or “annual” travel insurance).
You may have noticed I haven’t paraded company names throughout this post and that’s because I think it’s more important for you to have trip insurance from any reputable company than to send you to one specific company that may or may not have the right coverage for the type of travel you do.
I personally use RoamRight and have nothing but good things to say about them. You can buy annual travel insurance by entering tomorrow as the start and end dates of your policy, with the deposit as today’s date. The total trip cost should be $2500, $5000, $7500, or $10,000 (whichever is applicable to your normal trip cost). As long as you select ANNUAL from the drop-down menu, you’ll get a full year worth of coverage.
It’ll only take you about a minute to get a quote, so there’s really no downside to looking.
Travel issues are real and happen to everyone, so for frequent travelers, shopping for multi trip insurance makes a lot of sense.
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This post was not sponsored -- I genuinely use and recommend travel insurance.
I may receive a commission if you choose to purchase insurance through RoamRight; if you pick a different company, I won't be offended. Please do share your experiences with other companies in the comments for other travelers.