Tips for planning a surprise trip

For all the travel planning logistics I do, there’s one trip a year I can always count on where I can be fully hands-off: our anniversary getaway. It’s Tim’s trip—one that he researches, plans, and books…all without me knowing where we go. So when it came to gathering tips for planning a surprise trip, I knew exactly who to ask. 

Tips for planning a surprise trip

Know your person/know what they like 

Airbnb or hotel? Romantic? City trip? Beach getaway? Consider, are they doing other vacations? Do they often travel for work? If so, maybe plan something that is different from the norm. For instance, if they’re doing a lot of city trips, maybe steer towards something in nature. If they often travel for work, maybe a spa or relaxing getaway. 

TD: What is very tricky/important is planning the right mood for the surprise trip. For instance, when one or both of you are going through a hectic and stressful phase, it might not be the best idea to rush through Rome or London for 4 days. This could ruin the entire trip. Maybe prepare more than just one plan for the trip, depending on the mood. 

* Sardinia was beach / eat / repeat — exactly what we both needed.

Start planning your surprise trip minimum two months in advance

Tim advises you start planning your surprise trip at least two months in advance. This gives you enough time to do your research and make your bookings discreetly. Of course, so far we’ve only gone to “local” (within Europe) destinations. For longer-haul trips you’ll probably want a longer lead time, to get cheaper flights. When we surprised my mom with her first trip to Paris, we did it with a six-month lead time. 

Make a short-list of places that would fit the other

When planning your trip, it can be a bit overwhelming to decide where to go. Start by taking mental (or physical) notes of places the other has mentioned. Think of things they’re passionate about: tennis? Maybe a trip to Palm Springs to see a tournament. Game of Thrones? What about Dubrovnik or Belfast? Make a short-list of places that you can later narrow, with some rough ideas for each.

* I’d always wanted to visit Athens, but Naxos wasn’t even on my radar—and turned out to be a great fit for me.

Price calculation based on your budget 

Put together a budget. First, decide if the whole surprise is something you’re paying for, or if you’ll want the other to chip in. Because I know about the trip (but not the destination), we typically split our anniversary trip 50/50, and Tim gives me updates on the rough cost as we go. If you’re shouldering the whole cost yourself, make sure you can afford it. Creating a budget will help you manage the planning, and keep you from getting too extravagant with your offer. Some things to consider:

  • How many days do you want to go? 
  • How many layers of surprise are there? 
  • Are you going to pay for everything (food, accomodation, transport, attractions?) 

Confirm everything 

In the month before the trip, start confirming your plans. Car rentals, restaurant reservations, fast-pass tickets to attractions. Keep things organized, both so the other won’t find it, and to make things easier for yourself. 

*Because I plan and research our other trips, having this one trip where nothing is dependent on me is such a treat. I love just being swept along and getting to enjoy everything without worrying.

False hints and information 

How playful to you want to be? Tim loves to drop fake hints in advance of the trip, to scare me off the trail. Once, after a friend’s wedding, I was positive he’d drunkenly let slip where our trip was. Turns out, it was another layer in his surprise deception. 

Make it interactive

Tim’s biggest pro tip for planning a surprise trip?

TD: What I would definitely recommend is to keep at least one day free, so that your significant other has the chance to make adjustment or see things he/she always wanted to see that you are maybe not fully aware of.

On our trip to Paris, he planned a gorgeous evening, and a day full of activities for us. But our final day was all up to me. He had some things in his back pocket, but he also guessed I’d have some things I’d want to do, too. In the end, the trip is for both of you, and the other will definitely be happy to at least have the option to weigh in on extra activities—even if you’ve planned around their interests the whole time. 

* Visiting the D’Orsay was my contribution to our Paris trip.

Packing: Give just enough information. 

I know what you’re thinking—if this is all a surprise, how do you know what to pack? If your other doesn’t know about the trip at all, you’re going to have to do the packing for them. The times I’ve surprised Tim, I’ve squirreled away bits of his clothes in advance, or seized a moment when he was out to pack the whole suitcase. If the other knows there’s a trip, but not where, you can give a packing brief. Something like: warm and beachy, or, elegant city. If there’s a special activity on the trip, make sure to let the other know about it, especially if it requires dressing up (or dressing down!). 

Planning surprise(s) in the surprise trip

One way to keep the surprise going? Literally, keep them going. For our trip to Greece, I assumed the weekend away was just going to be Athens. I didn’t realize that in fact, we were only going to Athens for one night, and the other 3 days would be spent on a gorgeous Greek Island. The “nesting doll factor” was an added element I really loved, and Tim loved revealing.

* Full disclosure, my favorite part of that trip might have been the ferry ride itself, which was so peaceful and relaxing.

Think about the big reveal

Finally, think about the big reveal. There are two ways about it: spring the surprise in advance, and share the anticipation, or keep it a secret until the last possible second. If you want to share the surprise in advance, think about how you want to reveal it. For our surprise trip for my mom, I made a physical booklet with an itinerary for her to look at and explore, which we wrapped up for her birthday gift. Some other ideas could be:

  • A dinner themed to the location you’re going
  • A related book or film
  • A gift basket full of hints to the destination
  • A new item, focused on where you’re going (ie: a new bikini, thick hiking socks, tote bag, etc.)

Tim argues that it’s more fun to keep the surprise until you literally can’t anymore. This past year, he succeeded in getting me on the plane without me knowing where we were headed. He does through an elaborate airport ruse: taking me to the wrong gate (last time we waited ten minutes in a boarding line for a plane we were never going to take!), having me wear thick headphones, and keeping all signage out of the sight line. 

As the surprise-ee, there is a real thrill in not knowing, and I’ve never gotten to the end and regretted not knowing sooner. But you know your partner—if they’re going to want to pack their own bag or be self-conscious wandering around the airport with a blindfold, keep that in mind. The whole point is to have fun and be playful, not to add stress! 

Good luck planning your surprise trip! If you have questions or want so share tips or stories from successful (or unsuccessful) surprise trips, leave them for us in the comments!  

Need more ideas? I interviewed Tim about how planning our surprise anniversary trups here!