How to Gift a Surprise Trip and Don’t Mess Up

“There’s nothing more shockingly surprising

and awfully complicated than gifting a Surprise Trip!”


Gifting a travel to someone special is surely one of the most meaningful and creative presents you can make to that person. Things get consumed, get broken and forgotten while the memories and the learnings that a trip can give instead, are invaluable and can last a lifetime.

Doing it right though, it’s not easy like drinking a glass of water: saying the truth, quiet the opposite! A trip is a special and intimate gift that requires time to prepare, good care of the details and, of course, a smaller or bigger amount of good cold money. 

Dates, documents, accomodation, costs, transportation, activities…On one side, minding and planning all details can be chaotic and quiet overwhelming if not done with order. On the other, small unwanted mistakes should be kept to a minimum has they have the potential to ruin an otherwise great surprise.

Said that, don’t get discouraged! With the right effort and careful attention , you’re going to hit the target 100% and make that special person shiver with astonishment and joy! You can’t go wrong with a well-planned trip! 😉

In this guide, you’ll find all the information you need to prepare the perfect surprise trip for someone important, taking care of all of the details, avoid common pitfalls and overall, make sure you don’t mess it up! Enjoy 🙂

Let’s get started!

1. Set Your Budget

First things first: money.

As it goes with most gifts, also travelling requires some money (sadly…the hard reality of life!).

Before start planning the destination, length of the stay, transportation, accommodation, and all the rest; it is essential to set yourself the rough budget that you’re willing to spend for the surprise trip. 

Here are some Budget Guidelines you should follow:

  • Don’t go over your possibilities! Don’t try to impress by going beyond what you can normally afford. If you’re making a gift to someone special that cares about you, they will appreciate more the effort and feel that you put in preparing their gift rather than how much you pay for it! Moreover, you don’t want to create a distorted image of yourself that may lead to excessive expectations.


  • Set the maximum budget from the start. It is not carved in stone, but having a range for the maximum budget you’re willing to spend will help you sorting out the options in the next phases of the planning and discarding what doesn’t fit in. If in the end, you’re going to spend less (as you’ll see there are countless (COUNTLESS!) astonishing budget-options), good for you! Important is not going excessively overboard 😉


  • Consider whether you’ll go along or the person will go alone. If you’re gifting a surprise trip to someone special (ex. mum/dad, husband/wife, bf/gf etc.) you’re maybe planning it as a chance to spend quality time together with you. If that’s the case (as it is most of the time), consider that the budget will have to cover expenses for two!


2. Choose the Right Destination!

Choosing the right destination is crucial for making a memorable surprise.

Nowadays, thanks to the internet, the available possibilities at your fingertips are nearly infinite and it’s easy to get overwhelmed by all travel deals, last-minutes, packages, discounts, and so forth.

For now, let’s focus and just think about WHERE our special person would love to go; we’ll sort out the details later.

Here are some guidelines on How to Choose the Perfect Suprise Destination:


  • Discover the person’s preferences! If you’re thinking of gifting her/him a surprise trip, probably you know this person already quite good to know what she/he likes or always wanted to see. Try to remember if you ever talked about travelling (i hope you did!), analyze that person’s passions, and try to link them to someplace she/he’s never been before.


  • Ask them! Subtly! While you’re having a normal conversation, you could simply ask this person where she/he would like to go and see if she/he had the chance. Done right, it’s an innocent question to get to know a person better and shouldn’t give away any of your diabolic top-secret plans (muhaha!) 😉


  • Consider destinations that fit your budget. Be realistic. Depending on your budget there are options worth considering and options out of reach. If you’re planning to get a flight, now is the time to check Skyscanner to get an idea of the range of ticket prices and see if the trip is feasible.


  • Take into account the length of the trip. Staying fewer days could bring you further away and allow you to allocate a higher expenditure per day instead of having to spread the budget over a lengthier amount of time. Ultimately, it comes down to the kind of holiday you want to gift: a long-relaxing stay, an exciting short getaway, or anything in between.


  • Remember that the gift is NOT for you! It may ALSO be for you if you’re tagging along, but when choosing the right destination you have to keep the other person in mind first: their wishes, their preferences. If you’ll find a destination that both of you absolutely adore, bingo! Still, remember that you’re making a gift for her/him first of all.


  • Be sure it’s a good time to visit your destination. If you’re planning a trip to see the blooming sakura in Japan, you have to go in April. In the same way, if you don’t want to freeze to death, probably you should avoid Siberia in January. If you’re planning the trip for a specific month or a specific reason, check what’s best to visit in that particular period. Remember that seasons are inverted in the Northern and Southern Hemisphere!


3.Be sure The Person will have the time to go

When you’ll (more or less) have an idea on WHERE you would like to bring that special person, it’s time to find out WHEN!

For sure you have an ideal time-frame in mind, but will that special person be able to travel on those dates? Does she/he have already other scheduled events or appointments for those days? Will she be able to change them?

The worst it could happen is planning far and wide the trip and the surprise and then having to cancel it because that person is booked and not able to go (and the worst worst worst for your relationship would be you going alone on the surprise trip you “gifted” without her/him ! xD).

As we don’t want that to happen, be sure to follow the next tips to choose the right dates 😉


  • Investigate with people close to him/her. Friends, family, work colleagues. Ask the persons that know her/him better and could have the most information on her/his agenda, scheduled appointments, and plans.


  • Ask them! Subtly! (part 2 ;)) As a curiosity, you can always ask directly to the target person. Ask them when they’re going to have to time off if they can choose to shift work days if they have other plans during certain dates. Take out your sneaky side and get all the information you need, important is to be subtle!


  • Be patient. Be sure. Sometimes the urge to book a good deal may lead you to make irrational and hasty decisions. Breath, and be patient. If you’re going to book anything at all, you need 100% certainty that your special person will be free and able to go; if you don’t have it investigate more!


  • If you can’t be sure about the dates, leave them open. If the person is unsure about when she/he’s going to have time off and there’s no way to know for certain; your best bet is to leave the dates open. Budget the trip, make a good estimation of your costs, add a 10% more safety margin and you’ll be ready to reveal the surprise. Like this, you can always set the dates later when it’s more convenient for your special person.


4. Think 360° about All Costs!

Once you have a maximum budget, a destination, and fixed dates; it is finally the time to do the dirty work and to get creative! At this step, you’ll have to start thinking about all foreseeable costs you’re likely going to face and how to deal with them. To do that, do the following:

  • Calculate Travel Costs. Check the flight/bus/train prices for your dates (or if you’re flexible also in the days before and after) and have an accurate estimation. Will you need taxis to shift from airports or bus stations? Are there shuttles or trains available? Which are the costs? Add everything into travel costs!


  • Calculate Transportation Around. investigate what are the options to move around once at your destination and budget a reasonable cost given what you’re going to do there. Are attractions within walking distance? Is your special person fit enough to make it or she’ll need some help? Will you need some other transportation? What are your options? Write all down!


  • Calculate Accommodation Costs. Hostels, hotel, camping, Airbnb… which one will you choose? Depending on the kind of holiday you’re planning and the holiday-style your special person prefers, the cost may vary greatly. You can’t put your mother in a hostel after all! Don’t despair though, I wrote this article 15 Essential Apps for Smart Travelling to help you save on all aspects of travelling, from accommodation to transportation, eating and more ;


  • Calculate the Costs of Attractions. If the lifetime dream of your special person was going to Disneyland, perhaps if you gift her a surprise trip to Paris you’ll have to think about how to get her there! Consider the cost of activities you’re likely to do once or must-do once at destination: how much do they cost? Am I going to pay for those too or will she/he have to pay for her/himself? Is it a reasonable amount? This leads us to the next two points.

  • Decide which costs you’ll pay for. Evaluate your budget and consider what you’re willing or comfortable to pay for. Are you gifting a flight ticket or a whole experience? Will you draw the plan of the trip, are you going to do it together or you’ll leave it open for the other person? Gifting a trip can be tricky, be conscious about what the other person could reasonably expect if you gift her a surprise trip. 

  • Be sure you’re not forcing unwanted expenses onto your special person. Think thoroughly: if you don’t pay for the totality of the trip, will the other person still be happy about your gift? Will she face expenses (ex. accommodation) that she can and wants to afford? Am I putting her in a weird situation? If you know your special person well, you won’t have a hard time answering those questions!

  • Leave a 10% allowance for smaller/unforeseen expenses. When budgeting a trip, I always suggest keeping the upper margin slightly loose. There are always small expenses hidden in the cracks (can be tiny taxes, shuttles, Wi-Fi, touristic fees etc.), sometimes they’re a bit more than expected, most of the time less. Just keep them in mind!


  • Have the journey plan well sketched-out and double-check for hidden costs. Once you’ve done all your investigations, it’s time to draw the sum. Put everything together and check the total: is this within your initial budget? If not, can you tweak some aspects to make it fit? Budgeting and planning are reiterative processes; take your time and you’ll come out victorious with the perfect trip in hand 😉


5. Be sure your Present is Appropriate,

and They’ll accept it

Now that you know where, when, and how much your surprise trip will cost you, you’re almost ready for booking! 

Before that though, look at everything you prepared, look at your relationship with that special person you’re thinking of surprise, and ask yourself: is all of this appropriate? Simple question, simple answer. The worst would be that special person not feeling comfortable accepting such a gift from you and refusing it.

To be sure that won’t happen, do the following:

  • Be sure your relationship makes a trip an appropriate gift. If you’re gifting a trip to your working boss, to a partner you’ve met just a few times before, or somebody you don’t know too well, they may decline your gift as it could be too weird, too much, too soon, or anything in between. A trip is something precious, valuable, and potentially intimate; it is a gift you should make only to the people closest to you which you know better.
  • Be sure the gift is not excessive. Also for good relationships, there’s a limit on how much you should spend, don’t go beyond that! You don’t want to hear that flattering “you didn’t have to!” turning into a serious “you don’t have to!” or “we can’t”. Spend reasonable! Once more, remember: the best gift is mainly about your effort and love in preparing it and the actual time you’ll spend together sharing it; not how much you spend on it!

    If you’re sure of the above, let’s move forward and take care of all the practical details. 

    6.Get The Documents you Need,

    and Book the Trip

    We have everything planned and we are sure that it’s going to be an amazing and memorable surprise trip. Now what is left is to book it!

    To do that, follow these guidelines:


    • Get the Documents you need. Sort out all documents your special person will need for traveling. You may need their ID, passport, or driving license for booking, can you get your hands on those in a sneaky way? (or just take a photo of them?). Does she/he has them already or will she/he need to apply for one? Documents are of key importance for traveling, take great care of the details!


    • Double-check expiration dates. If the essential documents of the other person have expiration dates away and beyond your planned trip, then all good for you. If not, you may need to talk to him/her to get new ones and perhaps just reveal your surprise ahead of time to give his/her the necessary time to prepare everything for the trip.


    • Check for Visas. Do you need any? Can you get them beforehand by yourself or do you need the other person’s collaboration? Some places are harder to get than others, be sure to check which Visa you need (if any) and how can you get it (on arrival or do you need to apply beforehand).

    • Think about stipulating travel insurance.  If your destination is abroad (being it an exotic location, a faraway country, or just a neighboring land) you should definitely think about stipulating travel insurance (especially if you’re gifting a trip to someone!) to cover for potential accidents or medical expenses. Better pay a few bucks and know that everything will be all right rather than risk it every time!

    • Book everything as planned. You have the documents, you have the plan, let’s do it: Book book book baby! ;D This is the most adrenaline part of the whole surprise process: you’re really doing it! 

    • Keep vouchers and reservation copies diligently ordered. As you’ll likely get all the tickets/voucher in your email (if it has to be a surprise, be sure to never use the other person’s email!), try to keep the order of everything, so once you’ll have to give the other person his/her travel documents you’ll have an easy time find them all and make a comprehensive packet.

    7. If you’re Unsure about the Details,

    Leave space for Freedom

    Are you wondering what your special person would prefer to do once reached the destination? Will she/he prefer cultural attractions or leisure activities? Sunbathing or hiking? Disneyland or Louvre? If you’re unsure, leave the smaller details for later:


    • Leave enough space for the other person to sketch her/his daily plan. Everybody has obviously different preferences when visiting a place. As tours, museums, and all daily visits can be normally be booked just one day in advance (if not the same day!), don’t reserve those yet! Leave the other person the chance to customize his/her surprise trip according to his/her taste!


    • Research available options and give her/him a detailed list. The more unexpected and surprising the destination, the higher is the likelihood that the other person won’t know about the activities available on site. Giving them a list of options available is a kind and thoughtful options which will show them that you put total care to plan the trip for them and provide them a chance to customize it to their liking.

      8. Double-Check the Whole Itinerary,

      Connections & Required Documents

      Everything should be correct until this point. But still, for the sake of avoiding making ourselves look like distracted idiots, it’s better to meticulously double-check all our plans and bookings. Better to find mistakes by ourselves rather than having the other person making us notice.


      • Check all the bookings, dates, and times. It happened to me (twice -.-‘) of booking a flight ticket or a bus ticket for the wrong month. Especially for long journeys involving several accommodation and transportation bookings, sometimes mistakes happen. When self-booking on the internet, pages may refresh and some options may be hard to notice: a double-check is never a bad idea!


      • Check Luggage Allowance. How many kilos are included with each ticket? Is this enough? Know that extra allowance can be normally added up to a few hours before your flight/bus ride, so don’t stress too much about it; just be sure about what you booked already.


      • Check the Documents. Passports, insurance, visas, expiration dates, be sure everything is on point. It takes a few minutes to check, but better safe than sorry.


      9.Think about the Right Time

      to Reveal your Gift

      Rejoice! The hardest part is behind.

      Now you only have to consider which is the most ideal time to reveal your surprise gift and maximize the Wow effect!

      To do that, keep in mind:


      • The closer to the date, the higher is the adrenaline. That’s the rule of thumb! Nothing beats the kicks that announcements like “get ready, that in 3 hours we’re flying to Tokyo!” can give. Of course, the closer you get to the departure, the more detailed and precise your whole plan should be.


      • Leave enough time for packing if necessary. If you cannot pack for the other person or you’re just unsure about what he/she would want/need to bring; reveal your surprise before the actual leaving date (2-3 days before should be enough). The surprise will still be unbelievably great and leaving some peace of mind and time to get ready for the other person will make it even more enjoyable.


      • Leave enough time for that person to get organized if he/she’s not. Think about organizing work, asking for time off, updating documents, changing appointments… not everyone is free to just leave with the wind! Consider the context of your special person and try to assess a reasonable time-frame for when to reveal your surprise.


      • Think about revealing the trip but keeping the destination a surprise. This is a good compromise if you need your special person to get ready ahead of time, but still, you want to grow their sense of anticipation and adrenaline without spoiling the full surprise.



      10. Wrap the Gift

      and Reveal the Great Surprise!

      You have everything done: now it’s the time for the cherry-top!

      Receiving a trip as a gift is most of the time extremely unexpected; so why not transforming the already huge surprise into a truly jaw-dropping experience that will fill the lucky person with excitement and make them tremble with joy?

      Question is, how do you wrap a trip? How can you originally wrap something so immaterial? Something so wonderful but that that is not there yet? How do you reveal it to the other person to leave them speechless? Or it’s better to let them find it out? And if so, how?

      Those are all the questions I had to face once when I was planning to gift my girlfriend a Paris Getaway as a birthday present. I admit I took quite some time to think of all options and more, as I truly wanted to make it special.

      After a couple of days, I came up with 10 Creative Ways to Wrap and Gift a Surprise Trip, where I go through all my ideas and struggles to find the perfect way to reveal my surprise. If you’re also looking for an original, romantic, or funny way to unveil your present surprise, I am sure you’ll love my article and find all the inspiration you need 🙂

      Thanks for reading! If s you have other tips, ideas and suggestions, drop me a comment below! I love to hear new perspectives! 😀

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      1. Natasha

        I’m surprising my fiancé with a trip to Cabo. What’s the rule of thumb for gifts? Do you recommend I also give smaller thoughtful gifts as well?

        • Dani

          Hello Natasha! Why not giving the tiny gift making him believe that’s all? And then dadaaan, big big surprise ;D


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