How to give a surprise trip as a gift

Dec 13, 2021

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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 present … to give and receive. There’s just no question that a memorable travel experience is almost guaranteed to deliver more long-term happiness than another fuzzy 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. The pandemic slowed down that type of gifting at my house, but this may be the year that is right to try it once again.

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Even in normal times, 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.

(Photo by John Fedele/Getty Images)

In This Post

Be certain they’ll love it

If you can’t be 100% sure whether or not the gift recipient will love the trip’s itinerary and be available to travel on the scheduled dates (with an appropriate passport, COVID-19 requirements, 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 nonrefundable reservations) until you know for sure they want to go and are available.

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

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 their 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 numbers loaded into the reservation.

Related: Beginners 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.

Use an incognito browser

I won’t even pretend to know all the ways that the internet is always “spying” on you, but I do know that when I’m shopping for someone on one computer in the house, the others often start to get targeted ads for that item or destination. So, to cut down on the likelihood you tip off anyone that may live with you about the surprise, do your research and purchases in an incognito browser.

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 — even if it is your partner.

This is a bad idea for multiple reasons but on a practical level, they are likely to see the redemption in their account or inbox, so the surprise will probably be ruined.

Think about the ‘extras’

It’s a weird time, and so you need to think through things that used to just be extras when it came to trip planning. For example, if they need a rental car, you’ll want to make sure that price and availability aren’t going to be a problem.

Some ski resorts also limit lift ticket sales during peak dates, so if you are gifting them a ski trip, make sure they can still get lift tickets. Even Disney World sells out of tickets on certain dates, so ensure you make them Park Pass reservations to go along with gifted tickets in the case of a theme park trip tied to specific dates.

Basically, go through all components of the trip and pre-plan or at least adequately research the availability of all of the essential components.

(Photo by Summer Hull/The Points Guy)

Be careful of what the trip will really cost them

If you’re going to gift a trip (and that’s very kind of you), think through how much the gift will ultimately cost the person traveling. For example, if you’re giving them a cruise, will the recipient still be on the hook for flights to and from the port? What about a potential overnight at a hotel near the port and ancillary costs on the cruise? If so, is that still a reasonable “gift”? These days, you may also need to factor COVID-19 testing into the equation.

In the case of a cruise, those ancillary 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 actually 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 they 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. Hotels, Disney and even some cruise lines also all sell gift cards, making this a flexible way to gift travel without having to dive into a specific booking.

Related: The best starter travel credit cards

Wrap it up in a creative way

The gift of travel doesn’t need to be packaged in fancy wrapping paper 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, a trip to Spain using a huge map that your mom had 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, gift card or blanket, but it can also be way more rewarding for everyone involved if you can pull it off.

Featured photo by Isabel Pavia/Getty Images.

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