To Insure Or Not To Insure

Today I thought I’d cover a topic that is near and dear to my heart: travel insurance! Wait, did you just stifle a yawn?! Okay, I admit this isn’t at all the most glamorous or interesting subject, but hear me out.

You know how if you remember to bring an umbrella with you, it probably won’t rain? I thought travel insurance would work the same way (if you purchase it you won’t need it), but over the past several years, I have had the good fortune of purchasing travel insurance for trips where we actually ended up having to make a claim. There have been many times where we purchased insurance and didn’t need to make a claim, but for the trips where we did need it, the benefits were substantial. I’ve built it into our budget for most trips now since it certainly helps me sleep a little better while we’re away relaxing or adventuring.

The very first time I ever decided to add insurance to our travel plan was for our honeymoon in 2007, simply because that was one of the first “big” trips we were paying for ourselves and I thought travel insurance was the responsible thing to do. It turns out I was right – about a month before we were scheduled to travel to Aruba, Chris broke his collarbone in a gnarly mountain bike accident. (He’s okay now!) Thankfully I had covered the trip, so we were able to recover the full cost of the flights and the hotel and we were only out the small amount we paid for the insurance itself. If I hadn’t purchased the policy, we would have lost the entire cost for the trip.


Our 2011 trip to the Outer Banks, NC was thwarted by Hurricane Irene (we rerouted ourselves to St. John instead), and just last year a canceled flight due to mechanical issues caused us to miss a full day of our trip in Iceland. In each instance, we were able to get an appropriate refund – we were fully reimbursed for the Aruba and OBX trips, and we were reimbursed for the missed day in Iceland. Each instance was well worth the cost of the insurance policy.


Now for the disclaimer: I’m not actually an expert on travel insurance. There are a lot of variables and quite a bit of legalese that goes into policies and coverage, so just like reading medical advice on the internet you’re reading my advice at your own risk, but what I can tell you is what carriers I’ve used and what policies I’ve purchased.

I booked our honeymoon to Aruba through Travelocity and I purchased their basic Travel Protection plan without really reading into the specifics since I was new to the idea of travel coverage. Thankfully, that policy included trip cancellation for medical reasons. Chris did have a medical situation that would prohibit him from traveling, so we were covered. It was super easy to file a claim, and we were fully reimbursed for expenses that would have been non-refundable otherwise.

When we booked a beach house in the Outer Banks, the realty company, Twiddy, offered a third-party policy that included hurricane coverage and I (again, thankfully) decided to purchase it. This one also had a pretty simple claim process – just some light paperwork and a couple of phone calls.

By the time I booked our Iceland trip last fall, I was no stranger to the concept of travel insurance. I called my favorite provider that I’ve used for the past several trips, Travel Guard. How dorky is it that I have a favorite travel insurance provider? Answer: not dorky at all since it has translated to money back in our pockets!


Trip Cancellation and Trip Interruption are two of the top things I make sure are in our policy (Travel Guard has several different customizable options). Read the fine print though, and make sure you’re clear on what is considered an acceptable reason for canceling depending on the coverage, and what the exclusions are.

Some other things to think about: what do you need covered in your own situation? Are you planning an adventurous trip with extreme sports excursions? Maybe you should look into a little extra medical coverage, especially if you’re in a remote area where it could be extremely costly to be evacuated by helicopter. (I know it’s morbid to think about it, but better safe than sorry and broke, right?) Are you checking bags with pricey gear like dive equipment or expensive clothing like a wedding dress? Check out a policy with reimbursement for lost, damaged or stolen luggage and personal effects.

And if you’re completely unsure what the right plan is for you, you can either calculate a quote online or give Travel Guard a call. Everyone I’ve talked to has been super helpful on the purchasing end and the claim end. Let them know your trip details, your concerns, and even your budget, and they’ll be able to guide you toward a plan that will give you peace of mind for your travels. The policies I’ve purchased have been anywhere from around $100-$300, depending on the level of coverage and the cost of the trip, and since we’ve had to file three fairly significant claims, we’re still coming out way ahead at this point. Fingers crossed that we have lots of claim-free trips in our future!

Note: I’m not affiliated with Travel Guard in any way and I wasn’t paid to write this post; I just really believe in their products and excellent customer service!

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