Planning a surprise trip for someone is an exciting and fun way to integrate travel into your life. Finding any excuse, like a birthday or a promotion, is a great excuse to plan a surprise trip and celebrate whatever occasion it happens to be.

A few years ago we started planning surprise weekend getaways for each other’s birthdays as a replacement for a material gift and as an excuse to get a trip on the calendar. Over the years we’ve developed a system that works well for us and might work for you! Paces we’ve been together on surprise trips: Memphis (in our early years of dating), LA, Laguna Beach, Napa Valley, Sedona.

Step 1 to Planning a Surprise Trip:

Determine if you want the trip to be a complete surprise or if you just want the destination to be a surprise. There are pro’s and con’s to both approaches outlined below, the rest of the steps assume only the destination is secret.

Keeping the destination a secret and letting the person in on the idea that you are planning a surprise trip is the most exciting way to go. It builds anticipation for the upcoming surprise trip and gives you both something to look forward to. It also prevents awkward conversations or the chance that the person you are planning the trip for ends up scheduling something important for the dates you have your surprise trip planned. You also avoid having to pre-pack for them or having a big reveal the day before and only giving them a few hours to pack.

If you go the route of a total surprise here are things to consider:

  1. If the trip requires a day-off or days off work how will that be arranged?
    • One way is to contact their work/boss directly but that could be risky and it’s putting an undue burden on that person’s boss of having to figure out any planning/scheduling impacts that they might not normally be required to do.
  2. How will you avoid the recipient of the surprise trip from making plans for the desired dates?
    • One idea is to simply lie and ask the person to reserve the days for something else to throw them off the trail of the surprise trip.
  3. How will packing be handled?
    • You could either pack for them or do a big reveal the day or two before.

Step 2 to Planning a Surprise Trip:

Make sure that the dates you want to go on your surprise trip also works for the person you are planning the surprise getaway for.

It would really suck to realize that the dates you have lined up actually don’t work out for the person. Sometimes coordinating dates may mean not being able to go on the surprise trip on the targeted date, like their actual birthday or on the date of the celebration, but that’s OK because you’re still going to surprise someone with a trip and it’s going to be awesome.

Step 3 to Planning a Surprise Trip:

Do not use a shared credit card to book any portions of the trip.

If you have a credit card that is not shared, or that the person does not have access to the online statements use that to avoid them accidentally finding out where you are going. Nothing takes the winds out of a surprise trip’s sail quite like having the surprise revealed unintentionally.

Step 4 to Planning a Surprise Trip:

Make sure that the destination and activities you plan are in line with the interests of who you are planning a surprise trip for.

It can get a little exciting not to have to take anyone’s input into account when planning the trip, but the only input you aren’t getting is verbal. It’s important to honor the interests of the persons you are working so hard to surprise.

Step 5 to Planning a Surprise Trip:

Keep the surprise destination a surprise for as long as possible.

If you are flying somewhere print out their boarding pass and ask them not to look at it. Use sound canceling headphones at the airport so they can’t hear any gate announcements and hopefully they will play along long enough to avoid looking at where they are going. If you make it this far, you will successfully get them on the plane without them knowing where they are going and the cabin crew will be the ones to surprise them.

Bonus: let the cabin crew in on the surprise plans and maybe they make the destination announcement a little more exciting.

Step 6 to Planning a Surprise Trip:

Start building the anticipation.

This is where the fun really begins. About a week out start sending weather information about the surprise destination to the person you a planning the trip for. Also, include some packing tips. It’s a fun way to get the person even more pumped about their surprise getaway.

One of the best things about surprising someone with a trip is that you are intentionally prioritizing experiences and travel into your life. It’s an easy way to make an excuse to travel and changes things up enough to add some variety into your routine.

Let us know if you use our tips to plan a surprise getaway of your own! We’d love to hear how it turned out!

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Daina - Founder of headedanywhere.com

Daina - Founder of headedanywhere.com

Writer, Photographer

Daina is the sunset and ocean obsessed photographer and writer behind adventure travel and work-life balance blog, Headed Anywhere, featuring travel tips, photography, and hacks to simplify your busy life.

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