How to Plan a Surprise Trip

Whether it’s for Father’s Day, graduation, Christmas or a birthday, there’s no gift quite as exciting and surprising as a trip to a thrilling new destination. If you can manage to keep it a secret, that is — which is easier said than done.

But we’ll help you line up the perfect experience with this handy guide on how to surprise someone with a trip of their dreams.

How do you give a trip as a gift?

Keep the following tips in mind if you want to give a surprise vacation gift to a loved one.

1. Get the recipient's info

First things first: Bookings require some personal info, so before you start lining up a surprise vacation, collect all of the information you might need for airfare, train bookings, hotel stays, etc.

Here are the particulars you should have on hand:

• Full name as it appears on their identification.

• Date of birth.

• A copy of their passport (if booking international travel).

• Known traveler number for TSA PreCheck or Global Entry.

It is sometimes possible to book international travel without each travelers passport information, but you'll be required to submit it to the airline at some point before checking in for the flight. So if you can't get that info right away, look into the requirements of the specific airline you're planning to fly and find out whether you can add the passport information post-booking.

You’ll notice their email address and phone number aren’t on this list. That’s because you should avoid using their contact info, offering yours instead for confirmations. If you use theirs, one stray email about a tour or seat assignment could give it all away.

Travelers can always get credit for flights or accommodation post-vacation by logging into their respective accounts and claiming points and miles retroactively. A known traveler number, however, can be added to a flight booking without tipping anyone off.

2. Recruit a friend or family member

If you’re not already closely related to the trip recipient or living in the same house with them, it’s smart to recruit a family member, close friend or roommate to help you collect all of the information you’ll need. They can be on the "inside" as a co-surprise trip planner, assisting you in locating numbers, availability, etc. with less risk of you spoiling the fun.

3. Check (and double-check) their schedule

Before you begin the actual booking process, be sure to check — and then double-check — the trip recipient's schedule. The last thing you want to do is to book airfare, a cruise, condo or rental car just to find out they have a wedding that weekend or are celebrating a parent’s birthday.

With the help of your accomplice you've recruited, check work, social, school, even family activity calendars to ensure you’re not trying to surprise someone with a trip on a week they absolutely cannot leave home. Even better, consider making faux plans with them for something mundane during the trip time to ensure they're available.

4. Get insurance

When you book a surprise trip, check to make sure that any bookings you pay for in advance come with some sort of cancellation coverage (or at the very least can be rescheduled for no additional fee). If they aren’t, opt for travel insurance that allows you to cancel or reschedule any and all travel without hefty fees or penalties.

This way, if something does come up and the person you’re surprising can’t go, you — and they — are covered.

» Learn more: How to find the best travel insurance

5. Stay abreast of travel restrictions

Travel during the COVID-era can make surprise trip planning tricky, but it can be done. Research in advance any restrictions or travel bans that exist in your preferred destinations before booking. If you have to quarantine for two weeks upon arrival, but the gift recipient can only take one week off of work, for example, they’re not going to have a very enjoyable stay.

If they’ve been vaccinated and the destination requires documentation, make sure they have proof. And if they have to present a negative test before departing or arriving, coordinate so they don’t get turned away at the gate.

6. Keep it a secret

There's an art to figuring out how to give a surprise trip as a gift. Since keeping the vacation a secret can be tricky, especially if you live in the same space, it takes added consciousness and communication to not give it away.

Don’t leave tabs or your browser history open and available if you occasionally share a computer. If you share a bank or credit card account and the recipient checks it frequently, be careful not to use those cards and accounts to pay for travel.

Instead, purchase a Visa or Mastercard gift card, or sign up for a new travel credit card under just your name and pay for things that way. It's even better if you’re traveling with them and the card offers perks like free checked bags or lounge access.

Tell others in their circle that the gift is coming and that the news of it shouldn't be shared with the recipient — otherwise even if you can keep it under wraps, someone else might accidentally spoil the surprise.

7. Don’t forget the details

There are big things, like flights and accommodations, to think of, but don’t forget about the little things. Consider a car rental at the destination, comfort items like blankets or snacks for the trip and tours or bus tickets once they’ve arrived.

Are they driving? Consider gas cards.

Do you want them to eat well while they’re gone? Score a few gift cards to great dining establishments in the destination.

And when you finally reveal the surprise, offer informative things like brochures, travel guides and lists of helpful resources to help them get excited and plan any must-do activities.

If you gift a surprise vacation

How do you give a trip as a gift? With secrecy, stealthy planning, organization and a whole lot of creativity. But all of your hard work will be worth it when they take that first photo in their destination.