⚠️ Don’t take a risk with your next trip

We’re talking about risks in today’s newsletter. While we’re on the topic, here’s a risk that’s not worth taking.

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Illustration of a traveler at a sidewalk cafe browsing a travel insurance menu on a laptop

A menu of guarantees for weather nobody can promise. (Illustration by Dustin Elliott)

Buying certainty — Travelers keep paying for protection, and this year they are paying more even though the Atlantic hasn’t produced a single hurricane. Resorts and ski towns have joined the insurers in selling promises. But is it worth it?

On Backchannel, Larry Borden’s Honolulu cruise didn’t board until a day late because of a hurricane, and he’s asking whether his policy owes him for the hotel. We’ll have the answer.

For Members Only: Sen. Ed Markey and two colleagues have reintroduced a bill that would make airlines pay cash instead of vouchers when they cancel your flight. If this looks familiar, that’s because it is. Cash compensation has been proposed before and swatted down. So why should you care that it’s back? — Christopher Elliott

FEATURED ARTICLE

Is it worth paying extra for a “risk-free” vacation?

Celia Dunlap paid an extra $805 for travel insurance before a 40-day tour of Southeast Asia. Her operator cut the itinerary to 10 days, and the policy didn’t cover the cancellation, which left her holding a nonrefundable $4,500 airline ticket. Resorts and cruise lines are writing guarantees of their own now, and the promises sound airtight until you read the conditions. So what do these guarantees really cover?

🏦 “Escalated to a higher tier” — thanks to you!

Donald has spent months fighting Synchrony Bank and PayPal Credit over the same billing dispute.

But one thing worked: after we published Synchrony’s corporate contact information, he emailed the executives directly and got his case escalated to a higher tier of support.

“Thanks to the Elliott group for posting corporate contact info for Synchrony Bank. After sending an email, I was able to get my concern escalated to a higher tier of support,” he says.

We couldn’t help people like Donald without you. Thank you for your support. Here’s how to get our help for free.

OUR UNDERWRITER

Berkshire Hathaway Travel Protection covers consumers and their travel dreams, backed by Berkshire Hathaway Specialty Insurance Company’s financial strength and security. Choose travel insurance designed specifically to your trip and travelers, plus the fastest claims payments in the travel insurance industry. Get more information at Berkshire Hathaway Travel Protection.

📌 Here’s what you missed this week

Catch up on the latest stories from the Elliott Report

Is it worth paying extra for a “risk-free” vacation?
Celia Dunlap paid $805 for travel insurance before a 40-day Southeast Asia tour, and when the operator cut the trip to 10 days the policy didn’t cover her cancellation, leaving her with a nonrefundable $4,500 ticket. The Atlantic hasn’t produced a hurricane all season, and Caribbean bookings through one insurance marketplace are running 21% ahead of last year anyway.

Have we forgotten the lessons of 9/11?
Gateside by TSA PreCheck lets vetted travelers without tickets clear the checkpoint at 13 airports, and it arrives alongside the end of the shoe rule and a review of the liquids limit. A 2019 GAO audit found that none of nine vulnerabilities identified through covert testing had been formally resolved.

Pace the frontier? In travel, AI is already making our lives miserable
Air Canada’s chatbot told Jake Moffatt he could claim a bereavement discount after he flew, which wasn’t the airline’s policy, and the airline argued to a tribunal that the chatbot answered for itself. Algorithms already set your airfare and rank who gets the last seat out of a meltdown, and nothing requires anyone to tell you where you stand.

Is travel insurance useless in a crisis? Here’s what you need to know
Janice Lintz filed a claim after civil unrest in Nepal closed the airspace and canceled her flights, and her credit card policy denied it because no one had classified the protests as terrorism. Security memberships are absorbing the demand that insurance won’t, with one provider reporting nonmedical evacuation requests up 31% in a year.

Rover left my dog home alone for 17 hours, and now it refuses to pay the vet bill
Luke Gilbertson’s Ring camera caught his Rover sitter shut into another room for 17 of the 24 hours she was booked, while his dog, Stewie, vomited and later needed care for a swallowed object. Rover denied the $5,272 claim as an illness of undetermined cause and sent him $276 for the sitting.

Can Princess Cruises charge you more after you paid in full?
Deborah Keck paid $1,449 to upgrade to a suite on the Star Princess and got a confirmation marked paid in full with a zero balance. Princess added $3,967 to the booking months later, then told her to pay it, give up the cabin or lose the cruise.

Frontier Airlines baggage fees: When the sizer says yes but the agent says no
Benjamin Khoury measured his carry-on before a Frontier Airlines flight from Dallas to Phoenix and photographed it sitting inside the gate sizer. Frontier charged him $99 for an oversized personal item, then spent three months not answering questions about the photo.

OUR UNDERWRITER

Cavalry Elite Travel Insurance takes the worry out of travel by providing 24/7 access to medical and security professionals combined with the best medical evacuation and security extraction services. Cavalry gets you home safely when you need it most. Learn more at Cavalrytravelinsurance.com

💬 What you’re saying on Backchannel

Why isn’t my cruise leaving?

Larry Borden flew to Honolulu in August for a 16-day Norwegian Cruise Line sailing to Vancouver, and a hurricane near the islands kept the Norwegian Spirit from boarding until the next day. He covered a hotel room and two meals out of pocket, and he had bought travel insurance through the cruise line when he booked. Should he file a claim at all? Here’s our team’s advice on Backchannel.

OUR UNDERWRITER

EMBARK Beyond is a luxury travel advisory dedicated to creating thoughtfully designed experiences that go beyond a destination. Focused first on client needs, we have built (and continue to build!) relationships with the world’s most sought-after lifestyle and fashion brands to open the world - beyond imagination - to our clients. Find out more at EMBARK Beyond.

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