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Turn a Winter Travel Nightmare into a Dream Vacation

A common fear of travelers planning a trip during the winter season is the possibility of getting stranded at their travel destinations.

Rightfully so, as there is definite risk in visiting certain destinations during winter months. But with every risk comes the possibility of reward, even in winter travel!

What kind of reward, you ask, can come from winter weather interrupting a trip? Well, I’ll tell you:

When Winter Storm Jonas stranded us in New York City, we were able to turn the inconvenience into a second honeymoon - for FREE! And you could, too!

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The Storm

It was a January weekend in 2016. Our Friday afternoon arrival in the city was met with barely a snowflake. But by the time we were leaving Carnegie Hall later that evening -after a phenomenal show by Blues legend Joe Bonamassa, featuring cellist Tina Guo- the city was being pummeled by a full-on blizzard.

And it didn’t stop. For days!

Nothing but a paddle of ducks, the two of us, and a handful of hearty hikers in Central Park during Winter Storm Jonas

By Saturday afternoon, businesses were ordered closed. Busses and taxis were ordered off the streets. And of course, all airports were shut down.

Our Sunday afternoon departure was bumped back several times as the city and airports slowly dug themselves out from under 28+ inches of snow. We didn’t make it out until Tuesday afternoon.

This could have turned into an expensive nightmare. Except that it didn’t.

Because we played our cards right. Our travel rewards credit cards, that is.


The Second Honeymoon

You see, first of all, we had booked our flights using our Chase United Explorer card. As with many travel credit cards, Chase United Explorer automatically includes a trip delay reimbursement benefit for travel reservations made with the card. Meaning that if your trip is interrupted for qualifying reasons, you can receive reimbursement for food and lodging expenses up to a certain dollar amount.

With this travel card at that time, it happened to be $500 per person. And there were two of us. Which meant that we had up to $1000 to live on for what we guessed would be two additional days in New York City.

When a winter storm shuts down NYC, you might spot a local cross-country skiing down Fifth Avenue in Midtown Manhattan, like we did, just outside the Andaz Hotel.

Our hotel room at the amazing Andaz boutique hotel right on Fifth Avenue in Midtown Manhattan cost around $350 per night. (We had gotten the first two nights FREE, thanks to sign-up bonus points earned with our World of Hyatt Visa card.) So our lodging expenses for the two nights that we were stranded came to $700. That left us up to $300 for restaurant tabs.

Here’s where it gets even better: it happened to be New York City Restaurant Week. So as the blizzard calmed down and restaurants around the city began re-opening, we were able to enjoy amazing 3- and 4-course meals at prix fixe prices. $300 can put some pretty amazing dishes on the table during NYC restaurant week!


Your Turn

Admittedly, your chances of being lucky enough to get stranded in NYC during Restaurant Week are pretty slim, so you may not get this exact ROI. Even so, here’s how you can plan to replace worry with excitement when weather threatens your winter trip:

Know your credit cards’ benefits.

Check each card’s fine print or call their representatives. Find out which of your credit cards has travel coverage built right in. If none of them has it, get one that does! You can start with the two that scored us our great NYC trip, or check out another favorite of ours, the Starwood Preferred Guest AmEx card.

Make travel reservations with your travel rewards credit cards.

Presumably, this is fairly obvious. To make use of the benefits, you’ll need to have booked the trip with the card offering the benefits.

In a weather delay, make contact right away.

If a weather incident does happen during your travels, contact the credit card company immediately to determine the requirements for filing a claim. They will likely ask for proof that the trip was interrupted (for example a message from the airline, a weather report from a credible news agency, etc), as well as all receipts for costs incurred due to the weather-related incident. You won’t need to file the claim until you’re back home, but you will want to start gathering the evidence during the delay.

With these travel tips in your wheelhouse and cards in your wallet, go ahead and book some low season travel. Then you might almost wish to get stranded at your winter destination. I know we do!


Have you had any winter travel nightmares? Did they turn into dreams come true?

Tell us about it in the comments!


Looking for fun destinations for winter travel? How about:

Worlds of Fun WinterFest in Kansas City, MO

Gaylord Texan’s “Lone Star Christmas” in Grapevine, TX

The Best Holiday Events in the Midwest - recommended by Midwesterners

Pin this post for future travel planning!


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