How to surprise someone with a trip: the most detailed guide

list of places to go on a trip

Let’s show you how to surprise someone with a trip and make it memorable.

Is your anniversary coming, and do you want to gift your SO an unforgettable trip? Or do you want to plan a surprise trip for your family? Whichever the case, there are a lot of things you need to consider.

Surely, you wouldn’t want them to find out because that will remove the surprise element – and what’s a surprise without THE SURPRISE, right?

However, the sad part is, you can’t ask them where they want to go. So how do you now know if it’s something they’ll like?

Crazy, right?

But not to worry. That is why we have written this guide to walk you through the step-by-step process of planning a surprise trip for anyone. This article covers everything you need to know, from knowing where they would like to go to booking the ticket, down to the big reveal.

So let’s go right into the ACTUAL planning.

How do you surprise someone with a trip away?

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Photo by Leio McLaren on Unsplash

To surprise, someone with a trip shouldn’t be a daunting task. In summary, you need to find out when they’re off work, if they’ll love the idea, make sure the trip won’t cost the recipient, book the trip, and plan a memorable reveal.

That’s not the end (big grin).

Keep reading to see how you can go about it.

Know when they have time off, secretly

This is perhaps the most challenging task on this list. If you’re planning the trip for a 9-5er, or a student, you need to find out when their holiday or work break will begin. But you can’t ask them as it will spoil the surprise. So here are inventive ways that you can find out without asking them directly.

How to find out when the person will have time off

If they keep an updated calendar or schedule somewhere in their phone or house, you can simply borrow their phone to check it out.

If you’re planning it for a university student, try to check their academic calendar if it’s available online. Alternatively, you can ask their classmates when they’ll start their exams.

Another way to go about it is to simply ask them. It won’t spoil the surprise if you ask them randomly. If you don’t know how to go about it, tell us in the comment section. We’ll be more than happy to help you come up with the perfect way to ask the question without raising suspicion.

You may already know when your SO has days off if they have a steady job. But if not, you can talk to their boss to know the right time to plan the trip, that’s if the boss is a free person. Asking their coworkers is also a good idea.

Make sure the recipient will love it

Planning a trip is a romantic and thoughtful idea. However, it can be heartbreaking if the recipient doesn’t buy the idea. This is why we advise that you’re 100% sure that the recipient will love the trip itinerary, and they’ll be free on the scheduled dates.

If you’re not sure, make sure you don’t book any non-refundable reservations until you reveal the trip and you’re sure that your partner loves the idea.

What kind of trip should you go on?

Another thing you should figure out is the kind of trip you want to plan. By that, we mean, is it a solo trip, will you join them, or will they go with a friend of theirs?

Is it a solo trip, or you’ll join?

If you’re a travel enthusiast, you’ll probably want to join them and have fun. But if not, you can allow them to go alone or with a friend.

Will it be a long or short trip?

Short trips are the best to plan, especially if you’re keeping it as a surprise. Since you can schedule it to cover just a weekend, you won’t have to go through the hassle of asking their boss for time off. On the other hand, a longer trip is more exciting as they’ll have enough time on their hands to explore everything that needs exploring.

Are you going by road or air?

You would want to check in with your account balance on this one. The timing and length of the trip should also be considered. You’ll also want to take into consideration the person’s preferences. Does your SO or friend get car sick or hate flying? Make your plans based on what they would enjoy most.

Where will you stay?

Will you book an Airbnb, stay in a bed & breakfast or hostel, will you go camping, or are you planning to put up in a fancy resort? You shouldn’t consider finances alone. Take into consideration the places your SO/friend will like to stay.

Things you should not do when planning a surprise trip

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Photo by Jason Cooper on Unsplash

Don’t book the trip with the recipient’s email or frequent flyer account

The last thing you’ll want to happen is spoiling the surprise trip because the notification showed in their inbox or frequent flyer account.

Don’t ignore this, especially if the recipient is a frequent traveler. What you should do instead is book the trip with your account or register them as a new traveler, so their frequent flyer number doesn’t load into the reservation.

You can also make your bookings and reservations with a third-party website.

Don’t book the trip with their card or use their points

This should be pretty obvious. After all, you’re the one planning the trip, and so why should the recipient pay? Not only that, the redemption or invoice will surely appear in the inbox, which will bust the surprise.

Don’t gift a trip that will cost the recipient

If you want to gift a trip, you have to consider how much the recipient will have to spend on the trip. While it’s an excellent idea to plan a trip for someone, your friend/SO may not find it exciting if they discover that it’ll cost them.

For instance, if you’re gifting a trip to visit Joplin, MO, will the person taking the trip still have to worry about booking flights to and from the destination? Will they have to worry about where to stay while on the trip? How about booking experiences? If you total these things, it might run up to $1,000, depending on the details.

Therefore, you have to think it through so you don’t end up piling up bills that they’re not ready for or can’t handle at the moment. So if you can’t handle the expenses, better not book the trip as a surprise.

Leave the planning to someone else

Planning a secret vacation is a great way to show how much you love and appreciate someone. However, the whole planning process can overwhelm you, especially when you have many things on your hands.

Therefore, if you know the recipient’s available travel dates, you can choose to leave the planning to travel agencies.

Things to ACTUALLY plan for in a surprise trip (that you might forget)

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Photo by JESHOOTS.COM on Unsplash

Like we said before, planning a surprise trip on your own can be quite a handful. And because of this, you might start worrying that you have missed something from your plan. Therefore, we’ve included a few things that you need to include in your plans.

  • Flights: you have to plan your SO/friend’s getaway to and from your chosen destination. You can check third-party travel websites to get the best deals on your flight.
  • Transportation: Do you plan on renting a car when you get there? Or do you want to opt for public transport? Whether you’re going for any of these or using a tour bus, you have to plan it down and possibly make reservations in advance.
  • Accommodation: you definitely want to cover accommodation before you get there. Depending on where you’re going, you might find affordable hostels or Airbnb in the area.
  • Itinerary/sightseeing: Every city has tons of things to do, so planning an itinerary won’t be difficult. You can just Google search things to do in the city you choose or go to our destinations category to see what each city has in store for you.

Where to go on your surprise trip

Well, this whole article will be for nothing if we don’t add this section. After all, you have to go SOMEWHERE for it to be called a trip.


So, where should you go on your trip?

Well, you probably know the person you’re planning the trip for. Therefore you’ll have an idea of where they’ll prefer.

If you can’t think of any, simply just ask them. You can simply ask them about the top three places they’ll like to visit someday. Trust me, and they won’t even suspect a thing.

Additionally, we have a section of top destinations and things to do that you can browse to help you choose if you’re out of options.

How do you reveal a surprise trip?

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Photo by Ian Schneider on Unsplash

You don’t have to beat yourself about this. There are creative and simple ways to reveal your surprise trip. Here are a couple of options you can consider.

You can tell them straight or give them an envelope with the travel tickets inside.

Give them a novel set or travel guidebook about the place you’re visiting with the tickets inside as well.

Buy them a new suitcase, backpack, luggage tag, or passport cover and attach a note detailing the upcoming trip.

If you’re traveling to another country, you can search for a restaurant that serves the country’s food and take them there. Once there, you can reveal the upcoming trip as you eat.

When to reveal the surprise

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Photo by JESHOOTS.COM on Unsplash

There are primarily two times that you can reveal a surprise trip.

If the trip starts on an anniversary or birthday, you can surprise them that same day.

The second option is to reveal it in advance so that they can look forward to the trip on their big day.


As you can see, you don’t have to get all worked up on how to plan a surprise trip. We hope this article is able to answer some of your questions. If not, you can pop your questions in the comment section, and we’ll join you to plan the perfect trip. Good luck!

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