Planning a Surprise Trip for Someone – What You Need to Know

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.

So 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.

If you are planning a surprise trip where you need a passport, make sure you have all the necessary information beforehand. You need to know things like the other person’s exact name on their passport, the ID number, date and place of birth, and the passport expiration date. Also be sure to check whether a visa is required. If you don’t have the other person’s passport info, here’s what I said in order to get it: “Hey, I’m always watching for great travel deals. Just in case one comes up and I want to jump on it, I’d like to be ready with your travel info.”

Airline tickets also pose some unique issues. You can purchase tickets in your name for other passengers but remember, they may find out about the trip if they check their online airline account. One way around this would be to not include their frequent flier number on their reservation. That would keep it out of their account but that would also mean you would have to forego the award and elite status miles on their ticket until the information was added.

Here’s what I did… My husband is a longtime Delta Diamond so I knew if I arranged to fly Delta, he would see where we were going right away. Instead, I made the reservation through United Airlines. Yes, he has an account there and does sometimes fly United but knowing his travel schedule, I knew there would be no reason for him to check that account. It worked.

Alternatively, consider using airline miles and hotel points instead. One benefit to using them is that it’s easier to keep the trip a secret but be careful, you don’t want to forego a chance for upgrades or other benefits either. Another advantage here, depending on the travel provider and maybe your status with them, you may have flexibility to adjust your travel dates or redeposit the miles and points in your account without a penalty or charge if your plans change or don’t work out.

It should go without saying that if you are planning to surprise someone with a trip, that person needs to be someone you trust very much. A lot of travel costs today – and this includes hotels, car rentals, cruises, airfares, tours, and other costs – are frequently nonrefundable. If you purchase nonrefundable airline tickets, for example, and the other person does not go, any potential airline credit (possibly after change fees, depending on the airline) would actually go to them, not you. If you have any doubt, it may be wise to purchase the appropriate type of travel insurance.

I admit planning this surprise trip was a lot of work. There were so many pieces that had to fall into place perfectly, not to mention the research and creating all the daily clues and posting these blogs every day. But as I said at the top, my reward was enjoying all the comments trying to guess the destination as well as the expression on my husband’s face when he finally found out.

A side note never mentioned before, my husband narrowed his guess down to Copenhagen or Florence a few days before the trip began. While we have been to both cities, he leaned toward the first one because we have spent more time in the latter. Well, he guessed wrong and didn’t know where until we arrived at the airline gate. Even then, he didn’t know the destination was not just Florence but actually touring the Tuscany region of Italy.

Travel insurance may not be a bad idea. A travel insurance company worth checking out is Allianz Travel Insurance.

So would I do it again? Absolutely, a labor of love. My husband frequently surprises me, whether at home or traveling. Even on this trip he surprised me with a gold pendant replica of the first Florin coin used in commerce. Every time I wear it, I think of him and our surprise trip. These are the kind of trip memories that last a lifetime.

Be sure to read more about this, as well as thousands of more travel tips, in my book Business Travel Success: How to Reduce Stress, Be More Productive and Travel with Confidence.

I hope these tips help you out. Now check out these travel tips that will really have you enjoying your travels!

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p.s. Here’s a template for creating a fake boarding pass — I use this to create a personalized ‘announcement’ of the trip. Tuck it inside a book about your destination and voila! You’ve got a perfect way to gift your surprise.

About The Author

Carol Margolis

Carol Margolis is a travel-loving consultant, speaker, trainer and innovator who works with corporate travel management, HR departments, meeting planners and the travel industry -- and, of course, travelers! She offers tactics and tools to help travelers who want simple, fun strategies for traveling smart. Carol is a frequent TV and radio guest, appearing on Good Morning America, CNN, Fox TV, in USA Today, New York Times, Reuters and much more. Follow her at both SmartWomenTravelers.com and BusinessTravelSuccess.com. .