Make this vital purchase before your next vacation
Lots of things can go wrong when you're traveling.
Midway through an eight-day vacation to Venice and the Emilia-Romagna region of Italy in May, I received a text from the wife of my 72-year-old sister, Robin, telling me to call.
Before we'd left on our trip, I had visited Robin in a Philadelphia hospital, where she was dealing with complications from blood cancer, and she seemed to be improving. But her health had dramatically worsened and she was near death. We flew back to New Jersey the next morning and were able to see her before she passed away.
Compounding my grief was the struggle to get reimbursed for thousands of dollars in prepaid hotel, tour and assorted travel costs, plus a $430 surcharge for our rebooked flights back, and the tangling with our travel agent, United Airlines $(UAL)$, my credit-card issuer and our travel insurer.
My story isn't an isolated one. Summer travel season is here, and 67% of retirees are traveling as much or more than five years ago, according to luggage-delivery provider Luggage Forward. But there's a strong chance something will go wrong during many of those vacations, which makes a convincing case for buying a travel-insurance policy - especially if you'll be springing for a pricey trip.
"You're often investing a sizable amount of money for a vacation, and the world is a tricky, nuanced place right now," said Duncan Greenfield-Turk, founder of the Global Travel Moments travel agency. His take: Why wouldn't you protect that investment with a travel-insurance policy? It costs about 4% to 6% of your prepaid nonrefundable costs, which might be $200 to $600, depending on the trip.
Yet 63% of American travelers don't buy travel insurance, according to a 2025 survey by the Upgradedpoints website.
"People don't want to think about what could go wrong on vacation when they're planning one," said Suzanne Morrow, chief executive at InsureMyTrip, a travel-insurance comparison business.
They really should, considering that travel snafus have snowballed lately, including flight delays and cancellations, airline shutdowns, rough weather due to climate change and political instability.
When you're in your 60s or 70s, there's another potential worry: A parent, partner or sibling back home could have an urgent health problem (or die) while you're away, requiring you to return immediately.
My experience taught me eight lessons I want to share:
1. Don't expect your airline to offer a discounted bereavement fare. For many years, if you needed to take a flight due to a family member's death or impending death, airlines would offer a discounted bereavement, or compassionate, ticket. Now, however, most airlines don't.
The few exceptions (Delta $(DAL)$, Air Canada (ACDVF), Alaska Air $(ALK)$, WestJet and Qantas (AU:QAN)) typically charge 10% below full-fare prices for such fares and tend to require membership in their frequent-flier programs - and even then they often only provide discounts for certain flights and seats. What's more, these fares can be more expensive than their standard rates.
2. If you're hit with an airline surcharge for the emergency flight, ask for a refund. A last-minute rebooked ticket home will likely cost more than what you originally paid, as I learned when United charged my wife and me another $430 for our flights.
I contacted United through its website to ask for reimbursement and sent documentation of my sister's death. A few days later, the United Refunds department emailed, saying: "We know losing a loved one is never easy, so on behalf of our United family please accept our condolences. To help you focus on matters close to your heart, we've gone ahead and refunded the fare difference of your ticket to the original form of payment." (A United media representative confirmed to me that "we do not offer bereavement fares," adding that "customers who have questions about urgent travel can reach out to us via our customer-service channels.")
Not everyone in this situation will be as fortunate as I was with United. "You're kind of at the mercy of the customer-service department," said Jackie Mondelli, chief marketing officer at Squaremouth, a travel-insurance comparison business. Greenfield-Turk's advice: "If you fly the airline quite a bit and have status, leverage that when you ask for reimbursement."
3. Medicare might not cover you while traveling. Original Medicare excludes overseas medical coverage. Some supplemental and Medicare Advantage policies provide limited international coverage. If you have either, you should still check to see whether you'll want to buy a travel-insurance policy for broader protection.
"Medicare supplement plans typically come with a $50,000 limit on lifetime coverage overseas," said Whitney Stidom, vice president of consumer enablement at eHealth, an insurance marketplace.
For a domestic trip, Medicare Advantage plans cover emergency care, but routine care means either paying out-of-network costs or possibly not having coverage at all, depending on your plan.
4. Buy travel insurance directly from an insurer or from a comparison site. Tour operators, cruise lines and airlines also sell travel insurance, and credit cards sometimes include it for customers. But their coverage tends to be skimpier and often costlier than policies sold by travel insurers. Cruise lines often don't provide cash reimbursements; instead, their coverage is typically a credit toward a future cruise.
Once you've found one or more potential insurers, tell them where you plan to go, how long you'll be traveling, the types of things you'll be doing (some policies won't cover adventure travel), and any reason you might need to end the trip early or cancel it. "If you feel anyone close to you may pass or is critically ill, discuss that openly with the insurance professional you're working with," said Greenfield-Turk.
If you have a pre-existing health condition, ask about a waiver that will cover medical expenses for it if necessary.
"Just because a plan is more expensive doesn't mean it's better. You have to look at the benefits offered," said Mondelli. "We always recommend choosing the lowest price with the benefit coverage you're looking for."
5. Look for a comprehensive travel-insurance policy or a "cancel for any reason" policy. Comprehensive policies typically include coverage for trip interruptions, trip cancellations, lost or delayed baggage, medical emergencies and emergency evacuations. Here's something that might surprise you: Some trip-interruption policies reimburse up to 150% of costs because they cover expenses incurred for your new travel arrangements to return home (like my airline surcharge).
"'Cancel for any reason' is exactly what it sounds like," said Chrissy Valdez, senior director of operations at Squaremouth. "If you went to the salon a week before your trip and don't like the way your hair turned out, you can cancel your trip."
These policies (generally not sold in New York state and Washington state) pay 50% to 75% of nonrefundable and prepaid trip costs and cost about 40% more than standard comprehensive policies.
"Cancel for any reason" insurance often includes trip cancellation coverage. I bought such a policy, and it's why nearly all my prepaid travel expenses were reimbursed.
But here's where I screwed up: A travel-insurance premium is a percentage of the prepaid expenses you tell your insurer you'll have, and I provided mine with a figure that wound up being far lower than my actual expenses. As a result, my policy didn't fully cover all my out-of-pocket costs. Instead, it covered only up to a limit based on what I'd said.
The lesson: Before buying travel insurance, know how much your prepaid expenses will be so you'll get the right coverage.
6. If you want a "cancel for any reason" policy, find out when you need to buy it and when you can cancel. You generally must purchase this coverage within 21 days of your initial trip payment, and you can't cancel less than two days before you're due to depart.
7. Should you need to return home early, don't expect reimbursements from your travel agent or the hotels or tours you paid for. "When the money has already been spent securing services, getting it back [from the company] is almost near impossible," said Greenfield-Turk. Added Valdez: "It's very common for tour operators to have a cancellation policy with zero refund, and we also see that with hotels and airlines."
8. For reimbursements, get ready to amass a boatload of documentation. Travel-insurance comparison sites like Squaremouth and InsureMyTrip have staffers to help file claims and appeal denials. Roughly 20% to 30% of travel-insurance claims are denied, according to Squaremouth, usually due to missing paperwork or clerical errors.
My travel agent provided a detailed list of my prepaid expenses and a letter for my travel insurer confirming the "partial cancellation of services" for our trip. Once I had all that and my sister's death certificate, I emailed it all to the insurer and received my reimbursement about a week later.
Not everyone gets satisfaction that quickly.
"My mother-in-law, who lives in the U.K., came to visit us and ended up in the hospital for eight days, racking up over $40,000 in medical bills," said Morrow. "She had travel insurance, and it was a bit of a nightmare. They eventually paid because we were tenacious, but it took two-plus months."
-Richard Eisenberg
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(END) Dow Jones Newswires
July 09, 2026 10:30 ET (14:30 GMT)
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