Backpacking With Friends: Questions You Should Ask Friends Before Going on a Trip

I recently backpacked Wainwright’s Coast to Coast trail with two friends. Because I’m used to going on my adventures alone, I was a bit apprehensive. I’ve only known them for a couple of years, and we’d never done anything like this together.

So I headed online and searched for articles on questions to ask before going on a backpacking trip with friends. Nothing.  I decided to put together this article with questions that came up when we were planning our trip (and some questions that we should have asked, but didn’t). All in all, it was a fantastic trip, and we got along well—but I think we were pretty lucky. It can be hard to be with the same people day in, day out, while hiking long distances and carrying a heavy backpack.

Read on for all the questions you should ask friends before going on a trip with them—whether it’s hiking, backpacking, fastpacking, or something else.

Banner image by Paul Edney from Pixabay.

General trip preferences

There are some general questions you should ask friends before going on a trip with them to get an idea of what they want the adventure to be like. Remember, the more information you have during the planning phase, the easier it will be to align the experience with everyone’s wishes and expectations.

What’s your WHY? This is an important question, as it will inform a lot of your decisions and will help with your troubleshooting along the way. My WHY for the Coast to Coast was: to see a new part of the country, to stretch out of my comfort zone by camping along the entire way, and to go on a longer journey than I had before. I was also curious what it would be like to do it with other people, as I’m used to solo adventures. Ultimately, I just wanted to spend some time outdoors and enjoy the journey from coast to coast.

Podcast episode: Know Your Why For Your Outdoor Adventures

What type of accommodation do you want? We originally planned to wild camp as much as we could, and stay in campgrounds the rest of the time. We initially planned to book a B&B somewhere near the halfway point, but we ended up staying in a small country hotel near the end of the stay instead. Different people will want different types of experiences. If some of you want to camp and others want to stay in a B&B, perhaps you can plan your route so that you have both types of accommodation available at each stop.

What’s your budget? We didn’t discuss this in depth, but it was clear that we were all trying to keep things simple and economical by wild camping and staying at campsites. Your budget will determine where you sleep and what you eat. If some of your group are willing to spend lavishly, and others are on a strict budget, that could make things awkward.

What do you want to do for meals? Do you want to cook meals together or separately? Or do you want to eat at pubs and restaurants?

We planned to each cook our own dinners, and eat out occasionally. I brought eight freeze dried camping meals, and planned to buy more along the way, but this ended up not being necessary. I only used the camping meals when we were wild camping and staying in more remote places where other dining options weren’t easily accessible. We ate at pubs for dinner, especially when camping in a pub garden, and we ate breakfast a few times en route when passing through a town or village.

Image by Jordan Stimpson from Pixabay

How much of the trip do you want to plan? Do you want to map out every stage of the hike, or do you want to keep it flexible? Some people like to have a strict schedule; others like to have a general plan of what they’re going to do. Because I used to stay at B&Bs when I walked a trail, I had to have a strict schedule, as the B&Bs usually book up at least 3 months in advance. By camping, we had a lot more flexibility.

We discussed how many days we wanted to do the trip in (14) and then I created a Google Sheets spreadsheet that I invited everyone to. This mapped out each stage of the hike: the day of the week, the date, the starting location and stopping location for each day, distance in miles and kilometers, where we planned to camp, and a space for notes.

From there, we updated it once more when one of us spoke with friends who had camped along the trail a few years prior. We ended up splitting the route into 13 days of walking, with new estimated places to camp each night. We booked only the first night in St Bees, where we started the journey the following day.

Once we were on the trail, we changed everything around. We wild camped in different places to what we had planned, we took a rest day early on in the trip, and we stayed at a small country hotel near the end of the trip and not halfway through as we had planned. It all worked out perfectly, and it was wonderful to have the flexibility and the freedom to stay pretty much wherever we wanted—but this freedom was possible because we were camping. When we took a rest day in Shap, we tried to find a B&B to stay in and they were all booked up. It was a miracle that we found a hotel to stay at in Egton Bridge.

Image by Frank Winkler from Pixabay

Physical fitness

There are a few questions you should ask friends before going on a trip with them about their general physical fitness and performance. Don’t make assumptions. I suspect that my friends thought I was in better shape than I actually was due to my ultrarunning experience—yet I had zero experience hiking a 192-mile (309 km) trail with a 21 kg pack on my back.

What daily distance are you comfortable hiking? Everyone’s experience level will be different, and you’ll  need to find a schedule that works for everyone in the group. If two people want to power hike through 20-30 mile days, but the other two feel more comfortable with 10-mile days, it might be hard to find a happy medium.

When I first started thinking about hiking my next trail and camping instead of staying at B&Bs, I planned to only hike about 10 miles each day. I knew it would be a new physical challenge for me, and I didn’t want to overdo it. I wanted to ease into this new level of adventure.

But that’s not how it worked. We planned our days to be anywhere between 11 and 20 miles (yes, I admit I was worried about that long day), and most days were around 14-15 miles. In the end, we had not one, but two 20-mile days. It was tough, but I did it. And I was glad that I stepped outside of my comfort zone and attempted it, because now I know that it’s possible for me.

Are there any injuries or health issues that the others need to know about? If you have any health issues that might affect the trip, your companions need to know. I have asthma, for example. If you have any older injuries that might play up, it’s important to mention this also.

Image by Tim Hill from Pixabay

Hiking style

There are some questions you should ask friends before going on a trip with them about their hiking (or running, cycling, etc.) style and preferences. Everyone does their sport differently.

What time do you want to wake up in the morning, and what time do you want to get started on the trail each day? I am not an early riser, but from Day 1 we set our alarms for 5:00 am for a 6:00 am start, and that set the tone for much of the journey. Surprisingly, I found it easy to adapt. I was so exhausted by the end of each day, I was in bed by 8:00 pm or 8:30 at the latest, and one night I fell asleep at 6:30 in the afternoon! That made it easy to get up early in the morning, and it was nice to start early each day so we weren’t rushing to get to our destination each afternoon.

Do you prefer to hike together, or meet up in an agreed place at the end of the day? Each day, we all started together and finished together. We were a team. But we could have split up during the day, hiked at our own pace, and then met up in our agreed campsite at the end of the day. Do what works for you, but it’s good to discuss this first with your group so that everyone is comfortable with the plan.

What’s your hiking style like? Everyone is different in this respect. Do you want to put your head down and push on to reach your goal each day, or do you want to enjoy the journey and take lots of breaks? I’m in the latter group: I like to really enjoy the route and take lots of breaks during the day.

Your WHY for the adventure (see above) will inform your hiking style. If you’re doing this thing because you want a physical challenge, then it makes sense to put your head down and push onward through long days. But if you just want to enjoy the journey, then you might want to make it a leisurely stroll along the trail.

We ended up taking leisurely breaks every 5 km or so, because that’s about as long as my feet would last until they started to ache too much from the weight of my pack. When I hike alone, I often take breaks every hour or so. I’m not in a rush to get to my destination, and sometimes it’s nice just to be outdoors and sit and enjoy the scenery.

Image by Frank Winkler from Pixabay

Outdoor knowledge and experience

There are a few super important questions you should ask friends before going on a trip with them regarding their outdoor knowledge and experience. In order to keep your adventure as safe as possible, it helps to have done certain training, such as first aid and navigation.

Have you ever had an adventure like this before? This is an important question. It will help you to get an idea of just how experienced your companions are. I’ve hiked several long-distance trails here in the UK like the South Downs Way and the Ridgeway, but the longest I’d ever walked was 100 miles, spread out over 7 or 8 days. And I’d never carried all my camping gear for such a long time; the longest I’d ever backpacked before was a weekend.

Are you trained in outdoor first aid? I’m certified in outdoor first aid, and I’m about to renew it for the third time this year. While I’ve never had to put my training into use, at least I’ve learned what to do in a variety of emergency situations. Ideally, everyone in the group would have some kind of first aid training.

What are your navigational skills like? I’m certified NNAS Silver, and I’ve done the NNAS Gold training twice, though I haven’t yet done the evaluation. Though I haven’t put my advanced navigations skills into use recently, I do know how to navigate using a map and a compass. Ideally, everyone in your group would have this skill—otherwise, if the primary navigator gets injured, what will you do? You can’t always rely on technology to navigate—especially if your phone battery runs out!

Image by Tim Hill from Pixabay

Troubleshooting on the trail

There are questions you should ask friends before going on a trip with them that will help you troubleshoot on the trail in the event of any problems or unexpected difficulties. Better to plan in advance than to scramble to find a solution on the trail!

What if someone doesn’t arrive at the agreed-on place, and you don’t have mobile coverage to text/call? We didn’t discuss this, because we all stuck together during the day, but if you’ve decided to walk separately and meet up at the end of the day, what will you do if one person doesn’t show up and you can’t contact them? Do you assume an emergency has occurred, or do you assume that everything is okay, and the person has changed plans and is unable to contact you?

What if one of you wants to quit? Sometimes things don’t happen as planned. One of us had to drop out halfway through due to severe foot problems. But sometimes people want to quit an adventure because it didn’t meet their expectations, or it’s harder than they expected. How does your group want to handle this situation? Should the others encourage them to go on (assuming no injury), or should they accept their decision to DNF?

What if there are personal differences on the trail? If you find that your group isn’t getting along, you might want to simply split up: you might plan to stick together only as long as it makes sense to do so. But it’s good to discuss this in advance, so you aren’t stuck in an awkward position on the trail.

Image by Tim Hill from Pixabay

Special needs

There are questions you should ask friends before going on a trip with them about their special needs, whether it’s about their mental, emotional, or physical health—or their nighttime sounds.

Do you snore? Sleepwalk? All three of us snore, so that wasn’t an issue. I brought ear plugs but never wore them, because I got used to the sound of everyone snoring. I’ve never heard of a sleepwalking camper, but that sounds terrifying and dangerous—and something that your companions need to know about. Is there anything that the others need to be aware of regarding your nighttime activities?

Do you have any special needs? Are you neurodivergent? Do you have any special medical needs? Do you have any mental health issues? Phobias? It’s a good idea to let your companions know, so they’re better able to handle any issues that might arise in an emergency situation.

Fears and worries

There are also questions you should ask friends before going on a trip with them about your fears or worries. Getting these out in the open can help to reassure you and release any fears.

Do you have any fears or worries about the trip that you need to share? I didn’t share my worries before the trip, but I did talk about them a bit once we were on the trail. I was afraid that I couldn’t keep up with them, and while there were days that I was lagging behind, I don’t think it was a major problem—though we did adjust our schedule to allow for shorter days toward the end of the route.

Do you have any worries or concerns about traveling with me? This might be a tough question to ask, but it’s better to get any concerns out of the way before you start.

Read about my two adventures along England’s most popular National Trail in this second edition of my book Alone on the South Downs Way. This book contains all the blisters, sweat, and tears from my first life-changing journey—and all the joy, presence, and magic of the second one.

More than just a walking travelogue or memoirs of a walking holiday, this book contains my reflections on walking the trail, including lessons learned and practical information to help you plan your hiking adventure. It includes a suggested packing list, gear recommendations, and other useful tips, such as when to walk the trail, where to stay, and how much you’ll need to budget.