I can think of no better gift to give to others—or yourself—than a once-in-a-lifetime travel experience.

Undoubtedly, the upcoming holidays are going to look a lot different this year. The coronavirus will keep us at home, and any sort of gathering will be mostly virtual.

By now, we should be old hands at it. For most of 2020, we’ve kept to ourselves and our localities. That’s why when it’s safe to go out and about again—news of vaccines is making us optimistically look forward to 2021—we’ll be hungry to resume more far-flung travels.

On top of that, there’s really no better gift to give yourself or others than a travel experience. Surprising someone with a trip can be the ultimate present. A memorable travel adventure is almost guaranteed to deliver more long-term happiness than an appliance or gadget wrapped up in a bow.


If you’re thinking of a surprise summer trip to Alaska, remember that the more limited the infrastructure, the more imperative it is to plan early.

But planning a surprise trip can be difficult. It’s no easy feat to keep a travel destination secret from your family and friends until you’re actually there (or, at least, until you get to the airline check-in counter).

So, if you’re thinking of getting someone in your life a meaningful gift this year, here are 10 tips to help you make it happen.

1. Start planning early. 

You might be thinking of surprising someone with a summer trip to Alaska or perhaps arranging a surprise vacation to tropical Costa Rica during the dead of winter.


A surprise vacation to tropical Costa Rica during a cold winter could be the ultimate gift.

It’s important to remember that the more limited the infrastructure in the destination, the more imperative it is to plan early, since accommodations and activities will sell out quickly. And with the expected travel surge in 2021 after the worst of the COVID-19 pandemic passes, places are sure to get filled up soon.

2. Determine whether you want the whole trip or just the destination to be a surprise.

If you want to go with a total surprise, here are some things to consider: if the trip requires a day or days off of work, how will you manage that? You’ll also need to keep the recipient of the surprise trip from making plans for the desired dates. And, you’ll need to either do all the packing, or do a big reveal the day or two before departing.

A little less taxing on you and a bit more exciting for the gift recipient is letting him or her know that your present is a surprise-destination trip. That way you can be sure your schedules will work out.


You could let your gift recipient know that your present is a surprise-destination trip. But whether it’s a beach vacation or a cold mountain retreat remains to be seen.

Another option is to go the bait-and-switch route—announcing some ho-hum trip or other diversion that will lock the dates down for everyone, then revealing the true destination at the right moment.

3. Limit your accomplices. 

Divulge your secret destination only to the people who absolutely need to know. Don’t tell your children, other relatives, neighbors or anyone else who could accidentally let it slip. The safest way, of course, is to have a travel consultant do the planning for you.

4. Use a secret e-mail address.

Is there a chance that the person you’re surprising could glimpse your regular e-mail inbox? Have the trip-related communications—such as flight confirmations or hotel reservations—funnel into a secret e-mail account, which is usually easy to set up.


To further the surprise element, opt for a multistop flight. The extra travel time will give you the opportunity to play the guess-the-destination game.

Before departure, don’t give your giftee’s phone number to any of the travel companies involved in your trip.

5. Forgo using a shared credit card.

When booking the travel arrangements, use a private credit card for which only you have access. You don’t want your gift recipient to see related charges on the credit-card bill—online or otherwise. If you have joint credit cards and the co-owner is the one you want to surprise, you may want to use a relative’s card. Find a safe and private way of handling all prepaid costs.

6. Embrace flight connections. 

You may not have a choice in flight routes; but if you do, go for a connection rather than a direct flight. It sounds inefficient, but it will further the surprise element. You’ll spend the extra time in transit preoccupied with the guess-the-destination game. Connecting flights are usually less expensive than nonstops; so, if saving on airfare enables you to splurge on accommodations or on a unique, over-the-top activity to make the trip more memorable, consider it.


Tell your giftee she won’t need a passport; then take it along surreptitiously to keep anticipation alive.

Don’t use your gift recipient’s frequent flyer number—or hotel loyalty numbers—in the bookings. You don’t want your secret plan foiled by having the trip show up in the giftee’s frequent flyer account or e-mail. Be aware that that can happen automatically if you have booked a trip for the person before and the frequent flyer number is stored in your account. You may even have to enter him or her as a new traveler in order to bypass automatic loading into the reservation. There’s a chance that will make it more difficult to use TSA PreCheck (or a similar program), so there could be a potential downside to this form of secrecy—but it can keep your surprise under wraps.

And don’t use someone else’s miles or points to book a surprise trip. That person is likely to see the redemption in his or her account or inbox, and all your plans will fall through.

7. Pack peace of mind by purchasing insurance.

Planning surprise trips can up the ante of anxiety and stress. That’s all the more reason to buy travel insurance, which can help troubleshoot snags—from canceled flights to delayed bags—and provide financial protection for your investment.


Think of your recipient’s interests when planning your gift. If kayaking is a favorite activity, arrange a paddling outing in the destination.

8. Sync the destination and activities with the interests of the person you want to surprise.

If you know your gift recipient is always up for adventures, reserve a few exciting and unusual activities to engage in. Or if relaxing is your companion’s thing, arrange for a spa day or an afternoon kicking back on a beach.

It’s important to honor the interests of the person or people you are working so hard to surprise.

9. Build anticipation.

A week or two out from your departure, start sending weather information about the destination to your gift recipient and include some packing tips. It’s a fun way to get the person even more pumped about their surprise getaway.


If traveling to the Galapagos Islands, throw in a red herring. Tell your traveler to pack mittens. They’re small and won’t take up much room in a suitcase.

But do throw a few red herrings into your packing instructions. For example, you might mention that he or she will need a Gore-Tex parka, hiking boots, a sun hat, a swimsuit and a wool hat. If your giftee tries to ascertain the destination ahead of time and asks if a plug adapter is needed, answer “no” while packing a few extra ones. Or tell your traveler to pack mittens when he or she will actually be flying to the Galapagos Islands. If you know where your companion keeps his or her passport, say it won’t be necessary after you’ve already packed it for a trip to Portugal. That will keep your gift recipient perplexed and even more blown away when the revelation comes.

10. Do the small things that will keep the destination a surprise for as long as possible.

This is probably the most difficult task. If you are flying, print out all boarding passes (don’t send them to any cell phones) and keep them yourself. Ask the giftee to use sound-canceling headphones at the airport so gate announcements won’t be heard. Hopefully, he or she will play along with avoiding any clues until it’s no longer possible. The goal is to successfully get on the plane (train or other transportation) with the surprise still intact and having the cabin crew be the ones to finally end the suspense.

Vacation elevation

Surprise trips have the rare power to elevate vacations to already amazing destinations with the pleasures of heightened anticipation and receipt of a meaningful, memorable and once-in-a-lifetime present. Gifting travel may be riskier than giving a cozy blanket or a shirt, but it can also be significantly more rewarding for everyone involved. And if you feel that your planning skills for a surprise trip don’t quite stack up, don’t worry. You can always reach out to a planning professional to take care of everything.


I can’t think of anyone who doesn’t wish for a family member to be able to experience a dream vacation, at least once.

I can’t think of anyone who doesn’t wish for a family member, friend, neighbor or co-worker like you, who wants to couple gift-giving with a dream destination. Surprise trips have the potential to deliver the time of a loved one’s life—and the time of yours.

Here’s to finding your true places and natural habitats,