Travelling solo has its benefits - and so does travelling with a companion! That said, you shouldn’t underestimate how different it is to plan a trip for yourself versus with someone else. You don’t want just any travel companion, you want to find a travel buddy that’s good for you - whether that’s someone you know well or someone you met in a hostel lobby.

Disagreements can stem from things that seem obvious to you both, yet you may be surprised by your travel companion’s perspective while on the road. It’s best to be clear ahead of your trip, well before you start to invest your time and money.

Set up a coffee or dinner date to have a chat with your potential travel buddy — in a judgment-free environment — and use the questions below as a guide to cover all the bases in four steps: (1) travel preferences and logistics, (2) financial compatibility, (3) travel personality, and (4) emergency preparedness. And if you realise you don’t want to travel with this person, I also share some tips below on how to break that news. Let’s dive in!

IN THIS ARTICLE:

• Step 1: Questions on Travel Preferences & Logistics

• Step 2: Questions on Financial Compatibility

• Step 3: Questions on Travel Personality

• Step 4: Questions to Prepare for Emergencies

• How to Tell Someone You Don’t Want to Travel With Them

Travel Preferences & Logistics

First, let’s see how your travel dreams and styles align so you can start planning together. If you aren’t seeing eye-to-eye on more than a few of these questions, you might consider a different travel buddy. If you are seeing eye-to-eye on these aspects, then you can move on to financial compatibility.

Here are some key questions to help you and your travel buddy plan your trip:

• What are your expectations for this trip?

  • There are countless different approaches to travel. Whatever you hope to get from this trip, let each other know!

  • Is this a bucket list trip to hike a certain mountain? Are you aiming to see sites from your favourite movie? Are you just looking to relax? Are you aiming for afternoons of aimless wandering in new cities? Learning a language? Maybe there’s a certain type of food you’re looking to load up on?

• How long do you want to travel for?

  • A day or weekend trip is one thing, whereas a two-week road trip is another. Get clear on the travel timeline so you know exactly what you’re getting into.

• Where do you want to go?

  • You’ve probably already discussed a country or maybe a city you want to go to, but it’s time to narrow it down. Is that the right choice? If yes, where within that country or city can you go in the allotted timeframe?

• Do you want to visit multiple places? If so, how often do you want to change locations?

  • I used to move around a lot when I travelled, trying to squeeze in as many things as I could in as few days as I could. This is no longer my style - even though I do tend to squeeze things in a bit — I’m not fussed about getting to every attraction or site. I like getting to know one place a bit more intimately by spending more time there. Plus, it’s less exhausting!

  • So what’s your preference: Stay in one place for a week, or visit several places? This will be helpful to know!

• What types of accommodations / sleeping arrangements will we go for?

  • The options couldn’t be more different, so you’d best agree! Are you staying in a hostel dorm? Getting a hotel? Sharing an Airbnb rental? Separate rooms or sharing?

  • Who will choose where we stay? What star rating is your minimum?

  • Will you book in advance or pick when you arrive?

• What is your preferred mode of transportation from place to place?

  • You may also address this in the financial questions because transportation can be a big cost differentiator in many countries where private transportation is costly and public transport is cheap.

  • Be sure to discuss whether you are planning to use public transportation, rent a scooter or car (and who is driving?), use rideshares and shuttles, etc.

• What types of activities are you into?

  • This often comes down to the level of adventure and active lifestyle you each have, but also to age and accessibility.

  • For example, at the beach, there are people who love reading (me) and there are people who love surfing (other people). In the mountains, there are people who like to hike (me) and there are people who like to drink hot cocoa from mountain lookouts (also me). Know which one you each are!

• How active do you want to be during the trip?

  • Are there any big hikes or physical activities you’re planning for during this trip? Discuss them here.

  • For example: Do you plan to see the city on foot or by tuk-tuk? Do you like to go to the gym or attend workout classes during your vacations?

• Are there specific activities or sights that are musts for you?

  • Share your list of “musts” with each other and decide if there are any that you’d like to do separately or together.

  • For big cities, it can be helpful to create this list for different parts of the city (where attractions are clustered together) and/or to have a priority short-list.

• Do you enjoy trying new foods? What are your preferred meal options during the trip?

  • Some people really just like what they know, whereas others are super adventurous with food. If you’re a big foodie, you will probably enjoy travelling with a foodie who will walk 30 blocks to that amazing donut place with you.

  • If your travel friend is a super picky eater who will not be willing to try local foods or will only be willing to eat at familiar chains, you should know ahead of time.

Check-in on Step 1

• Are you on a similar page so far? If so, proceed to Step 2: Financial Compatibility!

• If not, you may want to consider another travel buddy, or taking the trip solo.

Financial Compatibility

Now that we know your expectations and travel styles are a match, you need to make sure you’re on the same page for the trip financially. That may sound dull, but this can be an early dealbreaker, so address it first. No one should put themselves at financial risk for the trip, and neither person should compromise on spending money they don’t have (or don’t want) to spend on travel.

Here are some questions and guidance to make sure you have financial compatibility before committing to travel with someone:

• What is your budget for the trip?

  • Use an approximate range and always overestimate for unanticipated costs.

• How flexible is your budget?

  • Sometimes, people with more money forget that others may not have the flexibility to splurge on something last-minute.

  • Some people are comfortable with charging things they cannot afford to credit cards (I can’t recommend this!) whereas others aren’t. It’s also good to know what contingencies you each have in place in case of emergencies.

• How would we divide costs and who will pay upfront?

  • In most cases, you are probably looking at an even split on all shared expenses, like accommodations, transportation and food.

  • In some cases, you might have an arrangement based on what each person can afford, or you might split differently based on how the assets are divided (ex. you may decide to pay more for the Airbnb since you’ll take the bedroom versus the common area).

  • Most importantly, be very clear about who is paying what upfront and what responsibility the other has to reimburse — including how and when.

• Where do you prefer to splurge? Where do you prefer to save money?

  • Whether it’s accommodations, transportation, food, tours or activities, each person has preferences for where they like to spend versus save on holiday.

  • I have friends who like to splurge on luxurious accommodations and make the most of them during the trip, whereas I usually view accommodations as a place to sleep and prefer to spend money on experiences and activities.

Check-in on Step 2

• Are you still on the same page? If so, proceed to Step 3: Travel Personality!

• If not, you may want to consider another travel buddy, or taking the trip solo.

TRAVELYNNE TIP:

• Use the free app Splitwise to track and settle your expenses!

• Don’t delay — start tracking expenses the minute you start spending — even if it’s months before your trip (ex. flights, hotel reservations).

• During dinner each night of the trip, do a quick check-in on Splitwise to make sure you’ve tracked each day’s expenses and to check in with each other that you’re comfortable with where you’re at budget-wise. You can always adjust your habits for the following days.

Travel Personality

Even if your potential travel buddy is your best friend, sibling or partner, you could be surprised by how different people are during travel. Some people are quite regimented, others thrive on the unexpected, whereas some prefer familiarity and others love to try new things. This is where “travel personality” comes in.

Unlike financial style, fewer of these elements are likely to be dealbreakers. It’s up to you to decide which of these could make or break a trip for you. With that in mind, use this section to set expectations for travel together.

Discuss these questions with your travel buddy to discover the best ways to live and explore together on your next adventure:

• How much time do you expect to spend together during the trip?

  • This is an important one! Some people truly plan to spend every minute together during travel and others are more independent, even in groups.

  • Inevitably, you will end up spending lots of time together with your travel companion(s), but personally, I believe that having some space from each other will make you a better travel buddy! This also depends on the length of your trip — space might not be as needed for a weekend spa trip versus a month-long Southeast Asia trip.

  • Time away from your travel friend can allow both of you to recharge and do things you love that others may not be into. For example, I might take time on my own to do some writing at a cafe or visit a museum that interests just me.

• How social do you like to be on vacation?

  • Is this a holiday to bond together, or are you OK with making new friends along the way? Are you going on dates while travelling?

  • Is it OK to invite people back to your shared Airbnb or to invite people from your tour to join your dinner reservation? For example, I was surprised once by a new travel companion who was not okay with me inviting others to join our tours, despite the fact that it would lower our costs. Be clear on these expectations.

• What’s your comfort level with planning versus being spontaneous?

  • This does not have to be a dealbreaker, as long as you can agree on your approach.

  • When I travelled for six months in a camper van with my ex-partner, I was a Type-A planner and my partner was an absolute non-planner, and we made it work. He did most of the driving while I did the planning on where we would sleep, get gas and restock supplies. We just agreed that I would do most of that planning while he drove so it wasn’t set too far in advance.

  • If you’re not too far on either end of the spectrum, flexibility can meet planning in a way that helps both people become less set in their ways.

• Do you snore or have any sleep habits I should know about? Are you an early riser or a night owl?

  • This can be critical to planning the best sleeping habits. Maybe you don’t want to sleep three feet away from a loud snorer or sleep talker, which is totally fair — separate rooms it is 😉

  • Knowing whether you’re looking for early starts or late nights will also help you plan things logistically, including the best activities and sleeping arrangements, and avoid having one person waiting on the other too much.

• Are you looking for parties at night or prefer to stay in?

  • In most cases, I am perfectly happy to get back to the hotel or Airbnb after dinner and go to sleep by 11 PM so I can get out again early-ish the next morning. But some people can’t imagine this and want to go out until 3 AM every night.

  • If all you’re doing is sharing accommodations, then maybe that’s fine, but likely you do want to be on the same page with this one so you don’t lose too much sleep.

• What helps you replenish your energy? What’s a good sign that you need a break?

  • In other words: It’s 2 PM, you’ve been walking around a city for 4 hours, it’s getting hot and you’re hitting a slump. What do you want to do?

  • Some people may like time alone, a nap, massage, swimming, rest in a park, workout, etc. Others may want to get a coffee and push through. This is good to know so you can each do what you need to fully enjoy the rest of the day.

  • If, for example, you tend to get cranky in the heat, can’t stand waiting in lines, or have hanger issues, you should definitely let your travel buddy know.

  • We all have our weaknesses, and that’s OK, but be transparent and have ideas on how to alleviate these issues and not turn them into arguments. Ex. finding A/C escapes, having podcasts on your phone for long queuing times, or stocking snacks in your purse to prevent snapping due to hunger.

  • While you should always communicate if you need a break, you can also let your travel buddy know of some of the signs that you need a break. For example, maybe you talk less, walk faster, get irritable, etc.

• How do you tend to handle disagreements?

  • Another important one. If you can’t agree on where to go, will you both be OK with doing your own thing and meeting up later? Will anyone resent the other?

  • If you feel the chance of resentment or argument is high, have a chat with your travel buddy, being sure to speak about yourself, how you handle conflict and disagreement, and what you hope for on the trip.

• Will you be posting on social media in real-time or looking to spend more time being present at the moment?

  • Listen, I love a good photo capturing me somewhere beautiful that I visited! But it’s more important to me to take it in, enjoy the moment and look at the beautiful place in question with my eyes.

  • I’ve travelled with people who really only cared about what the trip would look like on Instagram, and it was not pleasant. It involved wearing shoes they couldn’t walk in and me taking endless photos and videos of them instead of enjoying the moment.

  • Agree on what’s reasonable and respectful for each of you, and establish boundaries.

Check-in on Step 3

• Are you still on the same page? If so, proceed to Step 4: In Case of Emergency!

• If not, you may want to consider another travel buddy, or taking the trip solo.

In Case of an Emergency

If you’ve decided you’ll be travelling with someone, then it’s really good to know a few things in case of an emergency. Coming from experience, I can assure you that you don’t want to wait until there’s a problem to know who to call or how to handle it.

• Do you have any health issues I should know about?

  • You should know and share about things like allergies, physical health conditions, vital medications and mental health concerns.

  • If you have serious allergies, do you carry an EpiPen and does your travel buddy know how to use it? If you have a bad knee, for how long can you walk before needing a break? Or if you sometimes get panic attacks, is there something that makes it worse or helps calm you down?

  • You don’t want to surprise the other person at the time and vice versa.

• Do you have health insurance?

  • Please say yes! I’ve worked in foreign affairs and let me tell you, the people (or families of people) who call consulates with stories about being stuck abroad in dire circumstances are crazy. They never expect it, and often they are stuck with tens of thousands of dollars in debt after getting out of these situations.

  • Don’t wait until it gets to that - buy travel insurance, like SafetyWing, so that you are covered in case of an accident or illness. Share your travel insurance info with your travel buddy so they can help in case of an emergency.

• Who is your emergency contact person?

  • If ever an accident occurs, you don’t want your travel buddy to be the only person responsible for you. Let them know who you’d want them to call for support - whether it’s a friend, parent, sibling, etc.

• How do you handle emergency situations?

  • You never know exactly how you’ll handle emergencies until they occur, but you probably have an idea based on past experience.

  • Do you tend to freeze? Jump into fix-it mode? What’s your go-to response? It’s helpful to know if you have similar or different approaches to urgent situations so you can best utilize each other’s strengths (and make up for weaknesses) when the time comes.

Check-in on Step 4

• Still on the same page? That’s great news! It sounds like you’re all set to enjoy a great time together.

• If not, you may want to consider another travel buddy, or taking the trip solo. Below, you’ll find some tips for how to tell someone you don’t want to travel with them.

How to tell someone you don’t want to travel with them

If you’ve realized that the person you had in mind isn’t a good match for a travel companion, you need to have that conversation with them. This can be awkward but don’t delay it or wait until you’ve started booking things. Unless they’ve done something wrong, it isn’t fair to back out once money and time have been invested.

You can say something like, “I’ve considered our ideas about travelling together to [insert location], and I’ve decided that since my focus is really on [insert activity, ex. hiking, going to museums, partying, etc.] I’d better [go alone OR find someone who is also into that].”

If it’s a friend or family member, then I suggest also preparing an alternative idea to offer (ex. “maybe we could go to the [insert name] museum together on Saturday” or “Since we both love camping, how about a weekend trip to [insert park] next month?”).

Overall, my advice on this is: don’t delay, be firm in your decision and kind in your approach, and avoid casting criticism or blame by speaking from your experience or vision for the trip.

Enjoy your adventure with your travel friend — or solo!

As much as I love my solo travels, I have absolutely amazing memories with people I spent a few hours with abroad and people I travelled with for months. A lot of these tips came from learning by doing — which you will also have to do — but, if you have the benefit of time to prepare, then finding your ideal travel companion with these guiding questions can really help you have the best time.

I hope this guidance is helpful in your planning! Sign up for the Travelynne Explorer’s Club for free monthly travel tips and insights, and check out my other articles for more ideas, advice and inspiration for your next trip.

Special Note from Lynne

You can always trust that I am sharing my honest opinions and experiences with you on Travelynne and on my social media.

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