Step 1 to Planning a Surprise Trip:
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:
- 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.
- 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.
- 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:
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:
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:
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:
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:
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.
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!
Daina - Founder of headedanywhere.com
Videographer, Photographer, Writer
Daina is the ocean-obsessed videographer, photographer, and writer behind the underwater and adventure blog, Headed Anywhere, featuring videography and photography to connect you with our natural environments. Her goal is to help create a sense of wonder for our oceans and wilderness and create a connection so strong that it leaves you driven to protect our beautiful world.
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Hi! I’m Daina. I am an Underwater and Drone Photographer and Videography. I use visuals of the ocean as a spark to ignite the soul to create a connection with our natural environments. 
Daina I entirely agree with all of the points mentioned in this post! I have yet to plan a surprise getaway but will for sure refer to this when I do! =)
Thank you! I’m happy to hear you plan to use this as a reference!
What a charming read! You’ve infected me with excitement and I think I’m going to give this a try. Great photos as well! What is the mountain seen from the plane?
Thanks, Mark! It’s definitely something fun to try at least once! That photo is from when we flew home from Portland, so I am pretty sure that is Mt. Hood
Daina, this is awesome!! I appreciate the value placed on anticipation, and that you both share the joy. I love the mystery, and lengths you go to at the airport to extend the surprise. Brilliant.
Thanks, Anne! The build-up is definitely as much part of the excitement as it is to find out where we are going!
Such great tips! I’m always the trip planner and this will make it easier for my husband to plan something!
Thank you! I’m the trip planner too so when it’s my turn to not plan a trip its a nice little break (even though I really like planning trips hahaha).
This is great! I am planning a surprise trip for my wife, it’s 8 weeks to go till we take off (just for 3 nights)! She has absolutely no idea and I’m still debating if I should tell her one week in advance by giving her clues, or if I should tell her on the day/during the drive to the airport (I’ve already talked to her boss and got days off :)). Thinking of telling her we are going for a city break but then take the airport exit, wrap her passport up in gift wrap and give it to her when she starts asking why we’re going to the airport….. either way I’m trying hard to keep it a surprise and I’m slipping already!!!
That’s so exciting! Let me know how it goes!
Hi Daina, enjoyed your article very much. Your tips are spot on and very helpful. I think that the most important point is to choose the destination or activity both of you would enjoy.