How to give a surprise trip as a gift

Dec 19, 2019

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There’s really no better gift to give yourself or others than the gift of experiences and travel. Surprising someone with a trip can be the ultimate fun surprise for you and them. A memorable travel experience is almost guaranteed to deliver more long-term happiness than another sweater or gadget wrapped up in a bow.

Personally, I’m a sucker for putting slightly over-the-top gifts under the tree from time to time — including surprise trips.

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But giving a trip as a surprise can be complicated, or even disastrous, if you aren’t careful. Here are my tried and tested tips for gifting a surprise trip to a close friend or family member.

Giving a Surprise Trip
The magic of Christmas morning (Summer Hull/The Points Guy)

Be certain they’ll love it

I’d argue that if you can’t be 100% sure whether or not the gift recipient will love the trip’s itinerary and be free to travel on the scheduled dates (with appropriate passport, etc.), you shouldn’t book the trip as a surprise. You can still surprise them with the idea of the trip, but don’t make the actual bookings (or at least any non-refundable reservations) until you know for sure he or she wants to go and is available to travel.

Related: These are the hottest 20 travel destinations of 2020

Don’t use frequent flyer numbers in the booking

The easiest way to have your secret plan foiled is to have the trip show up in the recipient’s email inbox or frequent flyer account. This will almost invariably happen if you use his or her frequent flyer or hotel loyalty numbers in the reservation. It sounds like an easy step to skip, but be aware it can happen automatically if you have booked a trip for them before and their frequent flyer numbers are stored in your account.

For example, one year I booked trips for both my mother and husband for Christmas, and both were already travelers in my United MileagePlus account. I had to enter them as new travelers in order to not have their frequent flyer number load into the reservation.

Related: Beginner’s guide to earning points and miles

In the end, it all worked, and once Christmas had passed, I added their United frequent flyer numbers and Known Traveler Numbers to the reservation. Booking through a third-party site, such as Expedia, and leaving off the frequent flyer numbers can also work. There’s a small chance it will make it difficult to use PreCheck (or a similar program) if the names don’t 100% align, so there could be a potential slight downside to this form of secrecy — but it can keep your surprise under wraps.

Don’t use their points

This one should be pretty obvious, but don’t use someone else’s miles or points to book a surprise trip, for multiple reasons. And yes, this includes your partner! On a practical level, they are likely to see the redemption in his or her account or inbox, so the surprise will probably be busted.

Be careful when giving a trip that will really cost them

If you’re going to gift a trip (and that’s very, very kind of you), think through how much the gift will ultimately cost the person traveling. For example, if you’re giving a cruise, will the recipient still be on the hook for flights to and from the port; a potential overnight at a hotel stay near the port; and ancillary costs on the cruise? Is that feasible? Those expenses could total $1,000 or more, depending on the details, so think through if you’re accidentally signing someone up for expenses they may or may not be ready to handle. Again, when in doubt, don’t book the trip as a surprise.

Disney's Castaway Cay (Summer Hull / The Points Guy)
Disney’s Castaway Cay (Summer Hull / The Points Guy)

Consider gift certificates

One thing we’ve given extended family members in the past is airline gift cards, if we know the recipient likes to travel, but we aren’t in a position to know exactly when and where he or she want to go. This is an especially great way to give travel to grandparents who have grandkids and bucket-list worthy travel destinations scattered around the country and beyond.

Related: The best starter travel credit cards

Let someone else plan the details

Giving the gift of travel is an extremely generous way to show someone you care during the holidays. But it can also be complicated. So, if you know the recipient’s available travel dates, you could even consider giving them a mystery trip.

Surprise trip-planning companies like The Vacation Hunt, Magical Mystery Tours and Pack Up + Go will design a trip that satisfies the exact parameters of your budget, and use information from a survey to plan a surprise vacation perfect for the lucky recipient (or you, of course, if you’re giving yourself the gift of a stress-free getaway).

At The Vacation Hunt, for example, you can fill out the survey on behalf of the person you’re gifting a secret vacation — or you can buy a gift card if you don’t know the exact dates or duration. The Vacation Hunt can even work with miles and points, if you’d rather the gift come from that balance instead of your checking account.

Wrap it up in a creative way

The gift of travel doesn’t need to be packaged in fancy wrapping in order to be awesome. If you’re like me, however, it’s fun to strategize an unforgettable way for the recipient to discover the gift. For example, you could give a trip to Paris in a box of macarons, a ski trip in a box of fake snow or, in our case a few years ago, gift a trip to Spain using a huge map that your mom used in her high school Spanish classroom for over 30 years.

It isn’t totally necessary, of course, but it sure builds up the fun and excitement for everyone in the room as you can see by our trip reveal to my mom on Christmas morning a few years ago!

Giving the gift of a vacation may be a bit more risky than a sweatshirt, DVD or cozy blanket, but it can also be way more rewarding for everyone involved. If you’ve ever given a surprise trip, we’d love to hear what you did, how you did it and how it went!

Featured image courtesy of cdwheatley/Getty Images

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