I’m a solo traveler.

I love to travel on my own, explore new cities on my own, experience new things on my own.

And while there’s a lot to think about as a solo traveler, especially as a female, one thing you don’t have to think about is compromise.

The lack of comprise is one of the things I relish about solo travel.

Spend 8 hours in just one museum? No problem. Eat the same thing for every meal? Can do. Spend 30 minutes taking photos of just one attraction? No one is going to object.

So when a friend asked me to go on vacation, I was confronted with the fact that I couldn’t just book any hotel or come up with an itinerary filled with things I wanted to do.

Suddenly, I had to compromise.

And boy, were there more things to compromise on than I realized.

Because you learn a lot about a person by traveling with them.

And you learn a lot about yourself.

Here’s a list of questions to ask yourself and your potential travel partner(s) so that you can set expectations with each other and have as smooth a trip as possible.

The Questions

Pre-trip prep

• Where do you want to go?
• How long do you want to/can go for?
• When do you want to go?
• When is the deadline you want to have everything, or various parts of the trip (e.g. flights, hotels, etc.), booked by?
• If you are coming from different places, where and when will you meet?
  • What is your backup plan for meeting in case one of you is delayed?
• Do you have any medical issues or physical limitations the other person should be aware of or vice versa?

Budget and money

• What is your overall budget?
  • What is your budget for flights/car rental/gas/accommodations/etc.?
• How will you split the expenses?
• How will you pay each other back?
• Bonus: don’t forget to share discount codes!

Travel style

• Are you a morning person, a night person, or a day person?
• Do you want to spend any time by yourself?
  • If so, how much?
• What do you want to see?
• What do you want to do (see as many attractions as possible, shop the entire time, enjoy the local cuisine, attend festivals or other events, check out the nightlife, etc.)?
• Do you like to explore independently or do you want to join a tour?
• Do you have differing views and expectations on more controversial things like alcohol, sex, and drugs?
• Do you need to make any religious accommodations?

Eating

• Do you have any dietary restrictions?
• What are your eating habits?
  • i.e., Do you prefer to have a leisurely sit-down meal at a restaurant or are you more a grab-and-go kind of person?

Accommodation

• What type of accommodation do you want to stay in (hotel, hostel, camping tent, cabin, etc.)?
• What do you absolutely need at your accommodation (free WiFi, hair dryer, air conditioning, etc.)?
• What are your deal breakers (no shared bathroom, no unsafe areas of town)?
• Are you staying in the same room/dorm? Or are you getting separate rooms?

If things go wrong

• If conflict arises between the two of you, how are you going to resolve it?
• If there’s an emergency, what will you do (e.g., if one person cannot go on, will you stick together, or will the other person continue on without them)?
• In case of emergency, who should you contact among your travel buddy’s family and friends?

The How To

It might strike some people as too straightforward – or even aggressive – if you hand potential travel buddies a list of questions pertaining to your trip and travel style.

(Then again, some people might appreciate the straightforward approach. If that’s the case, more power to both of you.)

It’s best to be upfront about any dealbreakers before the trip. If your potential travel buddy just wants to party all night while you prefer to spend your nights sleeping and getting ready for full days of sightseeing…it’s probably a good idea to choose a different travel partner.

For all other questions, I’ve personally found that the best way to ask is to bring any questions up organically as the conversation goes – and don’t be afraid if some of this happens on the trip itself.

One friend and I ended up discussing important issues throughout the trip planning – and on the trip itself. Here’s a breakdown of when those questions came up:

Pre-trip:

• When and where to go, and for how long
• Accommodation
• Types of activities we wanted to see/do
• Splitting major expenses
• Where to meet (we were coming from separate cities)

On the trip:

• Eating habits
• Physical limitations (which were minor – major limitations should be discussed pre-trip)
• Splitting minor expenses such as meals/entrance fees/taxis

What was never discussed:

• How much time we would spend together (it seemed an unspoken agreement that we would spend nearly all day together, but don’t always assume that’s going to be the case!)
• Schedule (we didn’t even discuss whether we were night or morning people, but lucky for us this aligned)
• Emergency contacts or what to do in an emergency (thankfully, nothing bad happened so this wasn’t needed)

What I learned after planning a trip with a friend

Communication

Clear communication is important. It doesn’t matter what point of the trip we were on – at the beginning planning stages or in the middle of the trip itself – I couldn’t assume the other person knows what I’m thinking or can read my mind. I had to communicate, sometimes more than I realized.

Clarity is especially important if you’re dealing with a language barrier or cultural differences. The other person may not understand nuances if you’re not direct in your communication.

Always be respectful in your communication. While you want to be clear, you are dealing with another person, and they have feelings and needs too. Be mindful of that.

Don’t forget to check in with your partner. Be sure to ask about their feelings and needs. Just like you can’t assume they know what you want or how you feel, you can’t assume the same about them.

Be honest

Be honest and clear about what you need, especially if you have any dealbreakers. Don’t be rude or demanding, but if something is really important to you, be honest and stand up for yourself.

If you need something from your travel partner, be honest about it. When I travelled with an injury, I had to be honest and ask my friend to carry more of the luggage than normally I would have liked to have them do. But it was something I needed from them at the moment, and I had to be upfront.

Compromise

I had to remember this wasn’t just my trip; it was my friend’s as well. It didn’t matter as much what I wanted to do. I had to also be respectful and mindful of what they wanted to do.

One strategy I found to be helpful is asking what is the one thing that you each want to see or do on the trip. Once you both make your one thing known, build the trip around those sites or activities. That way, you both get to see or do what you have your heart set on. The rest is extra icing on the cake.

The other strategy is…

Flexibility

Trips are a microcosm of life. Things don’t always go according to plan. And that’s ok. If you and your travel buddy aren’t getting along, or one of you gets sick, or anything else comes up, adapt. It’ll save you a lot of headaches instead of rigidly sticking to your plan or only listening to your own wants and needs.

Let it go

Pick your battles. When my friend spent rather more time on their phone than I liked, I chose not to say anything – and I chose not to be mad about it. There was already enough we were dealing with. I figured this was a minor thing and I would just let it go. Not sweating the small stuff made the trip that much easier.

It’s ok

It’s ok to want to spend time by yourself. Let your travel buddy know. Most people will be understanding.

In the past, I’ve given people the silent treatment if I needed time to myself. Now I ask if I can have a time of time to myself, whether that’s exploring on my own for half a day or just having an hour or two in the evening alone.

It’s ok not to get along. Luckily, so far I’ve gotten along with all my travel buddies (most of the time), but in case you don’t, that’s totally fine. Now you know you don’t get along like you thought or imagined you would. There’s nothing wrong with that.

In fact, chances are, you’re not going to get along 100% of the time.

It’s ok to stand up for yourself. If you have dealbreakers, be sure to make this known, in a kind way. If you really need something, don’t be embarrassed about making it known.

Limitations

I had to be aware of my own limitations and how to counteract them. For example, I can be an absolute monster when I’m cranky. Making sure I had enough rest, food, and water was paramount in making sure I wasn’t an emotional drain on myself or my travel companion.

When my friend wanted to sightsee the entire day long, then go out for an event at night, I knew I physically wasn’t going to keep up at that pace. I suggested resting at the hotel instead and my friend was happy to oblige.

Kindness

Be kind to each other and take care of each other.  Again, check in with each other to see what you both need.

When my friend got sick, I had to make sure they were ok and not pushing themselves for my sake. Instead, I asked if it was ok for me to continue sightseeing or if they needed me to help take care of them.

Remember, it’s their trip just as much as yours. Doing what you can to ensure everyone’s needs are reasonably satisfied, you’ll all enjoy the trip much better.

Also, maybe treat them to something. I like to pay for a meal or buy my travel buddy a small souvenir. A little gesture goes a long way.

Enjoy

I almost always forget this one. I can get so wrapped up in all the planning and the details and the anxieties around a trip that sometimes I forget to simply have fun.

You’re never going to go on this trip with this person at this time in your life ever again. Enjoy it!

Hopefully now you’re a little more equipped for traveling with a friend. Anything I should add? Let me know in the comments!

P.S. In case you’re wondering how the trip went, it went off without a hitch – much to the delighted surprise of us both.