10 Things To Ask Before You Travel With Someone

Photo by Chan Young Lee

Traveling with a friend or partner is great; you get to go to brand new places and make memories of a lifetime. However, traveling with people can also be tricky. Even planning a trip with only one other person can be tough if you face different organizational styles or overall vision for the trip. Let’s say you’ve agreed on the destinations and a general time frame for the trip; now you need to agree on the way you’d like to travel.

Reflecting on all of my trips in the last few years, here are some big questions to ask to travel best with someone:

1. What’s your budget?

Everyone has a different expectation for how much a trip will cost, and the sooner you figure that out, the faster you’ll get an idea for what you’ll be able to do on the trip. Be realistic about the amount you’ll spend too — factor in the average cost of things at your destination, what types of accommodations you prefer, how many flights or trains you’ll be taking or even how much you’ll be willing to spend on meals. Also be clear about what you are not willing to spend money on. Maybe you’re not willing to splurge on a meal like your travel partner would; communicate all of that.

2. How do you plan?

So many things go into the planning of a trip and it’s important to know what everyone’s planning style is like. I make lists and Google Docs for everything leading up to a trip — budgets, accommodations, directions, packing lists, and more. I’ll also read through blog posts and online guides to find restaurants or attractions I want to go to and throw them all onto the doc. However, I’m generally relaxed about what actually happens day-to-day on the trip. The most important thing to me when planning is that all of the bookings are done well ahead of time. Be really clear about the way you plan, who is doing the booking and when, and how to divide up tasks evenly (in effort, time, and cost).

3. What’s the most important thing for you on this trip?

I love experiences that feel local and authentic to the place I’m in. In China, that might mean getting some really great food in places that don’t speak a lick of English. Your travel partner might want to check out some great art if that’s what they fancy or see the major sights. Agree on some of your must-haves and perhaps plan on days that you’ll spend apart doing your own thing. Better to realize that before leaving than when you’re there.

4. Who’s getting what before the trip and how are we splitting costs on the trip?

There are a lot of things you usually need to get before a trip. Perhaps you need to buy medicine, adaptors, and other travel supplies. Look to pool your resources and split costs on whatever you need. Also discuss splitting your costs during the trip. I like Splitwise during trips to keep track of who paid for what. That way, you don’t need to worry about settling each payment during the trip.

5. Pet peeves?

You might be someone that hates packing until the last minute or you love to take all the hotel samples. Congratulations, you’re Ross Gellar from FRIENDS!

Be clear on some of your travel habits since your travel partner might be someone that needs to pack ahead of time and hates clutter. Maybe you’re the type of person that likes arriving way ahead of time to airports and train stations and your partner isn’t. Perhaps one person hates getting lost and the enjoys wandering without directions. Find a place of compromise ahead of time and not when you’re lost and running to catch your flight.

6. Waking up early or sleeping in?

If your travel partner and you both enjoy waking up at the same time when you’re traveling, that’s awesome. Chances are, you’ll have an idea of this based on the every day sleeping habits of your friend but it’s always good to discuss this. If one person is an early riser and the other likes sleeping in, perhaps you can agree on one person doing some morning exploring every day while the other person sleeps in. It can be frustrating to discover this on the trip because one person will be long awake while the other will feel like they’re not getting enough sleep.

7. How do you react in uncomfortable situations?

There will be times when you’re lost or are in a totally unfamiliar environment. It’s a good idea ahead of time to paint a picture of those uncomfortable situations and understand how your travel partner will honestly react. For example, what happens if you turn down the wrong alley at night and cannot figure out where your tucked away hostel is? Or what happens if you show up at the wrong airport for your flight? Walk through some possible scenarios and get a good understanding ahead of time of how your partner will handle potential uncomfortable situations.

8. What happens if something goes wrong and it’s my fault?

This one is really important. Some people have a tendency to blame when they’re in a stressful situation while others are much more calm and understanding. Same with #6: paint some scenarios and understand what to expect. For example, what happens if one person gets the flight time wrong for a red-eye, and you end up having to sleep until morning to catch the next flight? Be realistic about some common travel hiccups and how you’d like to resolve them ahead of time.

9. What happens if you or I get sick?

When we think about traveling with people we love, we often don’t think about the potential of getting sick! Between the flights and the foreign food, it’s actually pretty easy to get sick. How will each person take care of the other, and how does each person like to get taken care of when they’re sick?When I get sick, I get really sick. I get cold, tired, emotional, and I feel totally guilty for wasting time during a trip. Other people might be the opposite. My partner likes space and sleep when he’s sick, so understanding all of that beforehand is awesome so everyone feels comfortable during the trip.

10. What happens when we need personal space?

I often feel like this question is avoided because personal space sounds like you need to get away from your travel partner. However, personal space is wonderful, especially if you and your travel partner have some differing interests. If I want to take my time checking out Modern Art and my travel partner has zero interest, they should take advantage of that time and go check out some sights they’re more interested in. Personal space is super healthy especially when spending so much time with someone.

Overall, aim to have the trickier conversations before you leave so you’re ready to be present on the trip. Hopefully, you’ll walk into your travels with your partner with a clear picture of what each person’s vision for the trip is and how to handle conflict and times when you just need a little space. On the trip, focus on quick resolutions and the big picture. You’re in an amazing new place!

Above all, be open to every experience and have an amazing time. You can follow along for more travel stories, photos, and videos @ www.janedays.com. You can also find my upcoming travel photos on my instagram. Happy travels!

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