Plan Them a Perfect Trip

stone structure in a sandy field overlooking a sunrise

How to plan a fun, personalized trip for a loved one, from departure through destination.

The best way to use up your vacation days is to plan a trip somewhere new. Even better? Planning a trip with someone you love. Doing research, finding places to go and things to do based on both your interests, and making the time to travel together makes it all the more fun.


Time spent is one thing, but a little planning is key to any successful trip. We all love to fly by the seat of our pants sometimes, but having some thoughtful ideas and touches will really help your giftee feel appreciated, and your trip go the distance.



The most important question: where do you want to go? This can be based on a few things, depending on whether your loved one is into nature, is more of a resort goer, or likes to roam the city. Think about what their interests are first and foremost, you want somewhere that they’ll feel happy and relaxed, but also excited about new prospects and possibilities. A few general ideas:  


  • Epic Landscapes:
    • Within North America, think locations with access to nature, hiking, and natural beauty. Tofino on Vancouver Island, Newfoundland, New Mexico, and Big Sur along the California coast are some incredible options. Make sure to research the best routes, hikes, National Parks, and beaches. As an extra touch, preplan things like snacks and activities for while you’re exploring.
  • City Life:
    • Big cities make great quick and easy getaways, are generally easy to access with major airports, and host a number of attractions for every kind of interest. This makes planning both fun and a little challenging, since your options can feel endless in cities like Toronto, New York, or Los Angeles. Do specific research based on their interests, and choose cities for their art, food, history, or sports.
  • Beach Vacation:
    • Does your giftee value rest and relaxation over everything else? The perfect beach getaway is probably your best bet. Do your research based on what they might want to get out of a tropical getaway: long sandy beaches, access to activities like surfing or diving, or proximity to nature. Make sure to think ahead and pack hats, sunscreen, and beach activities.


Getting where you want to go can often be the least fun part of any trip. Alleviate this for your loved one by handling all the planning for them, offer to research the best flights, book rental cars, and map out the best routes.


  • Drive:
    • Whether you’re driving to get from point A to point B or turning your getaway into a road trip, make the most of your time on the road. If you’re renting a car, offer to be in charge of logistics. If you’re driving a long distance, be in charge of mapping the route and following directions. Map out little places to stop along the way based on their likes and interests. Select playlists and podcasts that you know they’ll enjoy.
  • Fly:
    • If you’re off somewhere far away, flying is likely your best bet. Try to make the trip as direct as possible, nobody loves multiple layovers or long travel times. Pack good airplane snacks (don’t spend a ton of money on mediocre ones in the airport), reading material, or suggest you watch the same movie so you can chat about it after. Bonus points if you get them a neck pillow.


Be thoughtful. No matter where your trip is or what it looks like, adding personal touches and planning stops that are important to either their interests or your history together makes a difference. Choose restaurants based on the kinds of foods they like, and their dietary restrictions.

Have fun together. Plan activities that you’ve always wanted to do together, like tackling that long hike, or visiting that art museum, or seeing your favourite band live.

Document it! Take photos, keep a joint travel journal, and buy or create souvenirs from your time away. 

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