How to Plan a Surprise Trip for Someone

Is it your SO’s birthday? Are you celebrating an anniversary or wanting to blow your best friend away with the best Christmas gift ever? Above all else, do you and your special someone love to travel? Then perhaps it’s really time to treat them (and maybe yourself too) to a surprise trip!

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My fiancé, Arturo, had his birthday on August 31. I wanted to give him a gift he would never forget. We spent the past summer in Mexico City visiting his family. While there we missed seeing the Northern Lights four times in my hometown, Kelowna, BC. This was kind of disappointing for us because neither of us have ever seen the Northern Lights before. Yes, even though I’m Canadian I have yet to see them. My hometown of Kelowna is located in South-Western Canada and the Northern Lights are not a common sight there.

For his birthday I decided that we needed to see the Northern Lights. Since we are moving to Mexico indefinitely next June we might as well make the most of this winter in Canada. I’m excited to say that in November we will be going on a road trip to Jasper and Banff, Alberta. Hopefully we will be able to see the Northern Lights, go snowshoeing and visit some hot springs. So how did I plan this trip without letting him know until his birthday? Here’s how I did it and how you can plan a trip for someone you love as well.

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Find Out When They Have Time Off… Secretly

Planning a Surprise Trip

This was probably the hardest part. Arturo is back in school at UBC Okanagan this fall and I’m not so I wasn’t sure when the long weekends were going to be for him. I ended up finding UBCO’s academic calendar for this year online. Through this I was able to see that there would be a long weekend for Remembrance Day* (Nov 11).

A few ways you can find out when your friend or SO will have time off are listed below.

  1. If they’re in university, try to find their university’s academic calendar online. Alternatively you can ask one of their classmates for it.
  2. If they have a steady job you may already know when their days off are. Or you can try to talk to their boss to see if you can plan a few days off for them, without them knowing of course.
  3. If they keep an agenda or updated calendar either somewhere in their house or on their phone you can look at their schedule that way.
  4. You can straight up just ask them. I asked Arturo if he knew around which times of year he would have midterms. This was to double check and see if he would have midterms to study for around the long weekend. You could also get another friend to ask them so they don’t start to suspect that you’re planning something.

Figure Out What Kind of Trip To Go On

Winter Wonderland Kinsol Trestle
Near Kinsol Trestle on Vancouver Island BC; Photo by Arturo Padilla

There’s a few questions you need to ask yourself when planning a trip for someone else. First of all, are you going to go with them or are you going to send them away with a friend of theirs?

  1. Are you going to go on the trip with them? If you’re an avid traveler yourself you will probably want to do this and enjoy the trip with them. If you’re not but your friend or SO is, then you could always send them on a solo trip or plan a trip for them and another friend. One of my English students in Mexico told me that her husband planned a trip for her and her best friend once.
  2. Is it going to be a long or short trip? Short trips are definitely easier to plan when you’re planning in secret for someone else. This way you are less likely to have to ask someone’s boss if they can have time off. On the other hand, the longer the trip, the more fun is to be had!
  3. Are you going to fly or road trip? This totally depends on your financial situation as well as timing and how far you want to go. It’s all up to you but take into consideration your friend’s preferences. For example, does this friend or SO of yours get car-sick easily? Are the terrified of flying? Plan according to what you think they would enjoy best. I planned a road trip because we have access to a car and we’re saving up for our wedding so it’s definitely the cheapest option at this point.
  4. Where will you stay? Are you going to go camping, stay in a hostel or bed and breakfast or are you planning a luxurious stay at a fancy resort? Don’t just think about finances, take into consideration the kinds of places your friend/SO likes to stay.

International Trips

Chiang Rai Thailand
Wat Rong Khun (The White Temple), Chiang Rai, Thailand

If you plan an international trip for someone or with someone it’s going to be a little bit trickier. You will have to do the following things and may need to tell the person a little sooner than planned about the upcoming trip so they can do the following things.

  1. Passports. If you plan an international trip for someone you need to make sure that their (and your) passport is up to date. If they don’t have a passport or it isn’t up to date, you will have to tell them about your travel plans a lot earlier on.
  2. Travel Insurance. If you take someone to another country you will need to get travel insurance for both parties. While you may be able to purchase insurance for someone else you will likely need a lot of their personal information that you may not already have depending on who you are planning the trip for.
  3. Travel Clinics. It’s always a good idea to visit a travel clinic before you travel outside of the country. You could talk to someone at the travel clinic alone and if they say you and your friend will need certain vaccines then you will have to tell your friend about the trip earlier than you had perhaps planned.

Add a Personal Touch to the Trip

Palacio de Bellas Artes in Mexico City
Palacio de Bellas Artes, Mexico City

Has your friend been talking non-stop about a country they really want to visit? Maybe you and your SO met in a city that neither of you have visited in a while. Or perhaps your special someone’s favorite band is playing in a distant city. For Arturo and I it was that neither of us have seen the Northern Lights before, we missed seeing them while in Mexico, and we both really want to see them together.

The Big Reveal

Guide Books on Amazon
You could reveal the surprise by giving your loved one a travel guide!

When to Reveal the Surprise

There’s two times that you can reveal a surprise trip to someone. If you have planned it so that the trip starts on a birthday or anniversary you could surprise them that same day. The other option is to plan a future event and gift them something they can have to look forward to the trip on their special day. Since we were in Mexico for Arturo’s birthday and it was in August, I planned a future trip to celebrate his birthday in November.

How to Reveal the Surprise

Birthday Card for Surprise Trip
The birthday card I gave Arturo in the shape of Alberta, Canada

On his actual birthday I gave him a collage of a starry and colorful night sky with cut outs of snow shoes on top. This picture got him a bit confused but I told him it was a clue. Then I gave him a card that had the outline of Alberta surrounding a message letting him know that I was taking him to Jasper and Banff to see the Northern Lights.

Other ways you can let someone know about a surprise trip are listed below.

  • Simply tell them or give them an envelope with plane/concert tickets inside.
  • Give them a travel guide book or a novel set in the place you will be visiting.
  • Buy them a new backpack, suitcase, passport cover or luggage tag and attach a letter detailing the upcoming trip.
  • If you’re going to a different country, take them to eat that country’s food at a restaurant and tell them about the trip there. For example, if you’re going to take someone to Thailand then why not take them out for Thai food? You can tell them about the upcoming trip there!

Good Luck!

I hope this post has helped to answer any questions you may have about planning a surprise trip for someone else. Have you ever planned a surprise trip for someone else? Has someone ever surprised you with a trip? I want to hear about it! Let me know in the comments.

* I just want to say that while we will be having a fun road trip over Remembrance Day weekend we will also be thinking about all those who have died and lost loved ones during not only WWI but all of the wars and acts of terrorism that have occurred and continue to occur in the world today. We will be pausing in a moment of silence on the eleventh day of the eleventh month at the eleventh hour. To find out more about Canada’s Remembrance Day click here.   

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6 Comments

  1. Love this!! I had a surprise birthday trip two years ago and it was absolutely wonderful – you’re inspiring me to plan a surprise for my hubby now 🙂 Thanks for sharing!

  2. Best gift ever! I would love to do this for my husband some day. I have an idea in mind, just waiting for the right moment…Thanks for the tips on pulling it off!

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