Part 1 – Can You Plan a Surprise Trip for Someone? Sure!

Most people like surprises. Well, the good kind anyway. Longtime readers may remember when I planned a surprise trip with my husband a couple years ago. He had no idea where we were going except for the daily clues. Each day in December, I posted another clue to where we were traveling. It was fun to plan, fun to read all the comments where we were going, and so much fun to give away the prizes at the end.

FlorenceSo what’s involved if you want to plan a surprise trip for someone? It all begins with a destination. This might be something specific like Disney World, a cruise, a trip to the beach, or a larger geographical area like southern California. The next important ingredient is the amount of time. You need to know if you will have two days or two weeks. Then reality sets in because you need to have a budget.

Yes, there are a few more requisites. For most people, this means arranging time off from work for the other person. If it’s necessary, you can still keep the destination a secret but tell the other person they need to request time off for certain dates. That’s what I did and it worked out fine.

But there may be other pieces of the puzzle, depending on your living arrangements. If you have children who are not going on this trip, where will they stay and how will they be cared for? If the surprise is a family vacation, you and your partner can have lots of fun planning the trip but not telling your children where they are going. Each day you can give them a clue and share in their excitement.

If your surprise trip is an overnight getaway, you may be able to pack for them. Anything longer, few people can pack for their traveling partners. Of course, you will need to tell them what kind of clothing to bring. There is a world of difference between packing shorts and sandals vs sweaters or ski gear. If you are affluent enough, skip this step and just purchase all your needs once you arrive at your destination.

Next, decide how many clues, if any, you want the other person to have. In my case, it was daily in the month of December leading up to Christmas. And it takes some cooperation from the surprised person. My husband could have Googled the clues and probably figured it out but he was enjoying it much more by seeing what others were guessing.

Like with all trips, surprise or not, do you have any pets or other commitments that need to be addressed before going away? Preparing a checklist can come in handy.

If you have a shared credit card, it is possible your surprise partner might have online access and could see if you prepaid any expenses. That could ruin the surprise immediately. If this is an issue, there are a few workarounds. One thing you may be able to do is purchase gift cards through your credit card account, then use the gift cards to make your travel reservations. Another possibility is using a friend or relative’s account for the charges, then reimbursing them.

Depending on your shared account situation, you may be able to change the online password but you want to be careful here. Some people would look at this suspiciously and wonder what’s going on if they can’t access this information. You don’t want to create a problem out of such a fun event. If you have a really good trusting relationship, this shouldn’t be too much of a concern.

Part 2 tomorrow.



  1. Or you can just show sign up with one of the surprise travel agencies that specializes in this sort of stuff then you will both be surprised 🙂

    Oh and make sure the other person has a valid passport for international plans.

  2. Very timely post as I am in the middle of planning a surprise trip for Mrs. PWaC. Still trying to figure how close to our departure date I can even spring on her that we’re even going somewhere 😀

  3. PWaC — How fun that you’re planning a surprise trip for Mrs. PWaC! If it were me, I would want enough time to make sure all was taken care of at home (kids, pets, plants, etc.), enough time to ensure all was ok with my work and most importantly, enough time to pack. If the first two are not an issue, then one day should be enough! Update us on how the surprise went!

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