When Your Vacation Goes Sideways: Using Travel Insurance When Things Goes Wrong & Travel Disaster Toolkit

When Your Vacation Goes Sideways: Using Travel Insurance When Things Go Wrong & Travel Disaster Toolkit

Travel rarely goes exactly as planned. Flights get delayed, luggage disappears, somebody gets sick, a hotel reservation suddenly isn't what you expected, or an unexpected expense starts eating into money you carefully set aside for your trip.

For travelers managing a chronic illness, traveling alone, caregiving for someone else, or trying to make a vacation happen on a limited budget, those problems can become much more than an inconvenience. A few hundred dollars for an unexpected hotel room, replacement flight or medical visit can be a serious financial hit when you've spent months—or longer—saving for the trip.

That's one reason I think travel insurance deserves more attention than simply checking a box when you book your vacation.

Travel insurance can provide valuable protection when something goes wrong, but buying a policy isn't enough. You need to understand what you've purchased, know whom to call, document what happened and understand when the airline or another travel provider may be responsible before you turn to your travel insurance.

Here's what to do when your carefully planned vacation suddenly goes sideways.

First, Figure Out Who Is Responsible

When something goes wrong, your first thought might be, I bought travel insurance. I'll just file a claim.

Sometimes that's exactly what you'll eventually do, but travel insurance isn't necessarily the first place you should go.

Depending on what happened, the airline, hotel, cruise line, tour company or another travel provider may be responsible for providing a refund, reimbursement or assistance. Your regular health insurance or benefits provided by the credit card you used to book the trip may also provide certain protections.

For example, under current U.S. Department of Transportation rules, passengers on flights to, from or within the United States can be entitled to a refund when an airline cancels a flight or makes certain significant changes and the passenger chooses not to accept the alternative transportation offered.

So before immediately paying for everything yourself, ask questions.

What is the airline providing? Is the hotel refunding your reservation? Is the tour operator responsible for replacing what you purchased? Does your credit card provide coverage? Is this something your travel insurer needs to authorize before you spend the money?

When you're traveling on a tight budget, knowing who should be paying can be just as important as having insurance.

Keep Every Receipt—Even the Little Ones

If you have to spend money because your trip has been disrupted, start documenting those expenses immediately.

Save receipts for hotel rooms, meals, taxis or rideshares, replacement clothing and toiletries, medication, medical treatment and other necessary expenses. Your particular insurance policy determines what is eligible for reimbursement and what limits apply, so don't decide on your own that a receipt isn't important enough to keep.

I recommend taking a picture of each receipt with your phone as soon as you get it. Paper receipts have an amazing ability to disappear when you're tired, stressed, changing hotels or digging through your luggage.

Keep the original when possible, but now you have a backup.

And if an airline, hotel or other travel company reimburses you for an expense, keep documentation of that too. Your insurer may need to know what you've already received before determining what it owes under the policy.

Document What Happened While It's Happening

When you're standing at an airport after hours of delays, you're probably convinced you'll remember every detail.

Three weeks later, you may not.

Write down dates, times, flight numbers, reservation numbers and the names of the companies involved. Save cancellation notices, delay notifications, emails and text messages. If you talk to an airline, hotel or insurance representative, make a note of approximately when you spoke, whom you spoke with if you have a name, and what you were told.

For lost or damaged luggage, report the problem promptly and keep the baggage report or claim number. Take photographs of damaged luggage when appropriate.

You're creating a paper trail.

That documentation can make filing an insurance claim much easier later.

Call Your Travel Insurance Company While You're Still Traveling

Don't leave your insurance company's emergency-assistance number buried somewhere in your email.

Before your trip, save it in your phone and put it in your Travel Disaster Toolkit at the end of this post.

If you're dealing with a serious medical problem, stranded somewhere, considering emergency transportation or facing an expensive change in your travel plans, contact your insurer as soon as reasonably possible. Some policies have procedures that need to be followed or may require authorization for certain services.

Your insurance company's assistance service may also be able to help locate medical care, coordinate covered transportation or explain what documents you'll need for a claim.

For someone traveling alone, this can be particularly important. You don't necessarily have another person standing beside you who can make phone calls and sort through paperwork while you're sick, exhausted or overwhelmed.

Having that number ready means there's one less thing you have to figure out during an already stressful situation.

If You Get Sick While Traveling

For travelers with chronic illness, this deserves special attention.

Before traveling internationally, find out what your regular health insurance covers outside the United States. Don't assume that the health insurance you use at home will work the same way in another country.

Medicare generally does not cover healthcare outside the United States except in limited circumstances. Regular health insurance also may not cover emergency medical evacuation back home.

And medical evacuation can become extremely expensive.

That's why I want travelers—especially those of us already managing medical conditions—to look beyond whether a policy simply says “medical coverage.”

How much medical coverage does it provide? What are the exclusions? Is emergency evacuation included? Is there a deductible? Does the insurer require you to contact it before arranging certain care? Will you have to pay upfront and seek reimbursement afterward?

Those questions aren't particularly exciting when you're planning a vacation, but they're much easier to answer at home than from a hospital room in another country.

If you do become sick while traveling, get the medical attention you need. When appropriate, contact your travel-insurance assistance service, keep all medical bills and pharmacy receipts, and ask for copies of medical documentation that may be needed for your claim.

If you're trying to build a trip around health limitations rather than pretending those limitations don't exist, you may also want to read Make the Trip Work for Your Body, Your Budget, and Your Life.

What About Pre-Existing Medical Conditions?

This is especially important for the Spoonies reading this.

Having a pre-existing medical condition doesn't necessarily mean you can't obtain useful travel insurance. However, you need to pay very close attention to the policy's rules concerning pre-existing conditions.

Some policies exclude them. Others may offer a waiver of the pre-existing-condition exclusion when specific requirements are met. Those requirements vary by policy and can include when the insurance was purchased and other eligibility conditions.

Don't assume that because a policy advertises emergency medical coverage, your existing medical condition is automatically covered.

I'm creating a separate, comprehensive guide to travel insurance and pre-existing medical conditions, because this subject deserves much more than a paragraph buried inside another article. We'll look at what a pre-existing-condition waiver actually means, timing requirements, questions to ask before buying and what travelers with chronic illness should look for when comparing policies.

For now, the most important rule is simple: read the actual policy language before you buy.

Know What Your Travel Insurance Actually Covers

“Travel insurance” sounds like one giant umbrella protecting you against anything that could possibly ruin a vacation.

Unfortunately, it doesn't work that way.

Depending on the policy you purchase, coverage may include trip cancellation, trip interruption, travel delay, baggage loss or delay, emergency medical expenses and emergency medical evacuation. Each type of coverage can have its own definitions, dollar limits, covered reasons and exclusions.

Trip cancellation is a good example.

Standard trip-cancellation coverage generally doesn't mean you can simply decide you don't want to travel anymore and receive all your money back. The reason for canceling normally has to meet the policy's definition of a covered reason.

That's why I would rather see someone on a limited budget buy the coverage they actually need and understand than spend extra money simply because a sales page made a policy sound impressive.

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What About Cancel for Any Reason Coverage?

You may also see Cancel for Any Reason, commonly called CFAR, offered as an optional upgrade.

CFAR provides more flexibility than ordinary trip-cancellation coverage because your reason for canceling doesn't necessarily have to be one of the standard covered reasons. But that additional flexibility generally costs more, comes with specific eligibility and timing requirements, and normally reimburses only a percentage of the insured trip cost rather than 100%.

That doesn't automatically make CFAR a good purchase or a bad one.

It means you need to compare the additional cost with the amount of money you're actually putting at risk.

Travel Insurance When You're Already Traveling on a Tiny Budget

For my Broke Travelers, this may be the most important part of this article.

When money is tight, insurance can feel like one more expense standing between you and the vacation you're trying desperately to afford.

I understand that.

Instead of asking only:

“How much is this insurance going to cost me?”

I want you to ask:

“How much could I afford to lose?”

Suppose you're taking an inexpensive trip and most of your hotel reservations can be canceled without penalty. Your financial risk may be relatively small.

Now suppose you've spent two years saving for a major trip and have thousands of dollars tied up in nonrefundable flights, hotels and tours. Losing that money could mean you don't get another opportunity to take the trip for years.

Those are two very different situations.

Look at what you've actually prepaid. Determine what's refundable. Check what protections you already have through your health insurance and credit card. Then compare travel-insurance policies based on what you actually need protected.

And remember: a cheap vacation doesn't necessarily mean a cheap medical emergency.

That's one reason medical and evacuation coverage deserve separate consideration from the price of the vacation itself.

If the cost of traveling sometimes feels like the biggest obstacle standing between you and seeing the world, read Attention Spoonies: How to Travel Even If You're Broke: The Complete Guide to Seeing the World on a Tiny Budget. That's where we tackle the bigger question of making travel possible when your budget says otherwise.

Solo Travelers Need a Backup Plan That Doesn't Depend on Another Traveler

When two people travel together, there's another person available to make a phone call, watch the luggage, find the policy number, speak to the hotel or deal with paperwork while you're trying to solve the immediate problem.

When you're traveling solo, you're it.

That's why I think organization becomes particularly important for solo travelers.

Keep your insurance information somewhere you can reach easily. Have an emergency contact at home who knows where your important information is. Keep your hotel's name and address, your insurer's assistance number and essential travel details somewhere other than only inside your phone.

You don't need to prepare for every disaster imaginable. You simply need enough of a backup plan that one dead phone, missing bag or bad day doesn't take every piece of important information with it.

Lost or Delayed Luggage: Start With the Airline

If your checked bag doesn't arrive, report the problem to the airline promptly and obtain a baggage report or claim number.

Ask what the airline will reimburse for reasonable necessary purchases while your luggage is delayed and save every receipt for the things you buy. Take pictures of your paperwork and keep records of your communications with the airline.

Your travel-insurance baggage coverage may provide additional protection depending on the policy, but don't skip the airline's reporting process. Your insurer may require documentation showing that you reported the loss or delay.

And don't immediately replace half your wardrobe assuming somebody else will pay for it.

Ask what's considered reasonable and covered first whenever possible.

Don't Automatically Wait Until You Get Home to Start Your Claim

My original version of this article told you to file your claim after your trip.

I'm changing that advice.

You may ultimately complete and submit the claim after returning home, but don't assume you should wait until then to contact the insurance company.

Notify your insurer promptly when something substantial happens and ask what it needs from you. It's much easier to obtain documentation while you're still at the hotel, airport or medical facility than to track down the right person several weeks later.

When you're ready to complete the claim, you may need your policy information, itinerary, receipts, proof of the disruption, medical documentation when applicable, and records showing any reimbursement you've already received.

Keep copies of everything you submit.

What If Your Travel Insurance Claim Is Denied?

A denied claim doesn't necessarily mean you should throw the letter away and give up.

Read the insurer's explanation carefully and compare it with the language in your policy. If you believe relevant information was missed or misunderstood, ask the insurer about its appeal or claim-review process and provide whatever supporting documentation is appropriate.

If you continue to believe an insurer isn't handling your claim properly, your state insurance department may be another resource for information or consumer assistance.

This is another reason documentation matters so much.

The more clearly you can show what happened, what you paid, what you were told and what your policy says, the easier it is to explain your position.

FREE DOWNLOAD: My Travel Disaster Toolkit

I don't want you trying to remember all of this while you're exhausted, sick or standing at an airport wondering what you're supposed to do next.

That's why I created a free two-page Travel Disaster Toolkit you can save to your phone or print and take with you.

It includes:

- A Before You Travel checklist
- Important contact information
- What to do when something goes wrong
- An If You Get Sick While Traveling checklist
- Lost or delayed luggage steps
- Theft, scams and lost-item reminders
- An emergency-expense tracker
- A travel-incident log
- A final checklist for wrapping things up

Fill it out before you travel, not after the disaster happens. Get at the end of this article.

Keep a digital copy on your phone and, if it works for you, a printed copy with your travel documents. You can also leave appropriate information with someone you trust at home.

Travel Insurance Isn't About Expecting Your Vacation to Go Wrong

I don't think travel insurance should make you afraid to travel.

It's supposed to do the opposite.

For someone with plenty of disposable income, a canceled trip may be frustrating. For someone who saved month after month to afford that same vacation, losing thousands of dollars can mean losing the possibility of taking another trip for a very long time.

For someone with a chronic illness, the financial stakes can be even higher if medical care or evacuation becomes necessary.

And for someone traveling alone, simply knowing who to call and what to do next can provide something almost as valuable as reimbursement: a plan when there isn't another traveler standing beside you helping figure everything out.

Travel insurance won't cover everything. No policy removes every financial risk from traveling. That's exactly why reading and understanding your coverage matters just as much as buying it.

Know what you've purchased. Know whom to call. Know what documentation to keep. Find out what the airline or other travel provider is responsible for before assuming your travel insurer should pay.

Then go take your trip.

The whole point of having a backup plan is so you don't have to spend your vacation expecting something to go wrong.

Get there your way.

Want More Help Making Travel Work for Your Life?

Travel doesn't have to be perfect, and neither do your health, finances or circumstances.

Join The Single, Sick & Broke Traveler for practical help with solo travel, chronic illness, budget travel and all those little things that can make traveling easier in real life. Click on the Travel Disaster Toolkit to sign up and left click to download.


Insurance and medical disclaimer: This article provides general travel information and is not medical, legal, financial or insurance advice. Travel-insurance policies, benefits, exclusions, eligibility requirements and claim procedures vary by insurer, policy, state and individual circumstances. Always review the actual policy documents and contact the insurer or an appropriate licensed professional with questions about coverage. For medical questions and travel decisions involving your health, consult your healthcare provider.

The Single, Sick & Broke Traveler

Travel stories for the brave and budget-conscious.

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