Choosing Your First Solo Destination: 5 Questions That Actually Help

Jeju Island has incredible hiking destinations.

Choosing the destination is sometimes just as hard as actually going on the trip. I personally experience decision fatigue daily, so choosing somewhere as big as a vacation location feels nearly impossible. I’ve devised a few tricks to figure out where I want to go, and I wanted to share them with you because I’m sure I’m not the only one who struggles with both dinner decisions and vacation locations.

Over the years and hiking on three different continents, I’ve learned a thing or two. There isn’t a perfect place, but there is a right place for right now. And to get to the bottom of that place, you have to ask yourself a few questions.

Question 1: What am I actually afraid of?

Because you know some of this has to do with fear. Even my dinner decisions have to do with fear. I’m worried I’m going to waste a meal on a bad choice. We only get three meals a day. What if the one I chose is shitty? Devastation!

When I was choosing my Coast to Coast walk, I had a few fears. A few thousand, actually. They ranged from getting lost in the English countryside to… well, getting lost in the English countryside. I had never been to England, and my only reference was backcountry backpacking where getting lost can mean staying lost forever. Turns out England isn’t so scary.

Fear isn’t necessarily a weakness—it’s a data point. You can use your fears to help you decide where to go. When you write down all of those concerns, you can find answers to them. Or at least find destinations that can help ease the worry.

Question 2: How do I want to feel at the end of each day?

Truth of the matter is, I’m still working on this one. I will plan some aggressive miles thinking that “all I have to do is walk all day,” but at the end of a 20-mile day you can barely walk! Be honest with yourself about how you want to feel at the end of each day.

This question will help you plan your trip. Is it a death-defying Alps trek where you’re white-knuckling your hiking poles through treacherous mountain terrain? Or would you prefer a lovely 8-mile stroll through lochs and castles?

How do you want to end those days? In a pub or a hut? In a hot spring and bed, or a tent on the trail? Important questions when you think about how you want to experience the end of the day.

Question 3: What’s my backup plan if I hate it?

Oh, you thought we were going to skip the what-if-it-goes-wrong question? Nope.

Options are a good thing. They can save your ass in certain situations, but they can also offer freedom in others. It’s not about giving up—it’s about knowing what’s right for you.

I’ve had to bail on a hike. Very recently, in fact. While hiking the West Highland Way, my third day was a full-on struggle and took me way longer than it should have. The day ended in tears, and the next day started with the decision to get off the trail. But because I planned accordingly, I was able to get the bus back to Glasgow and decide how I would spend the next seven days rehabbing a knee and still enjoying a vacation.

When planning, you need to ask questions: Can I easily shorten the trip? Are there towns along the way where I can pause or pivot? Is it realistic to extend? Are there other travelers around, or am I truly isolated?

This isn’t about lacking commitment. It’s about being smart and knowing there’s a backup plan to the backup plan.

Question 4: Do I genuinely want to go there, or does it just look good on the gram?

Choosing a destination based on its Instagrammable moments is dumb. Especially for first-time solo hikers or travelers. Sorry, but sometimes the truth hurts.

Sure, base camp will give you street cred and incredible photos, but are you really ready for that? Let’s dig a little deeper and think about the reality behind those images you’re seeing on Instagram. What’s the true cost of those trips? Are you ready for the challenges of that experience? Do you really want that for yourself, or do you want it for your feed?

The experiences you’re about to invest in (financially) and experience (emotionally) should be for you. They should feed your soul, not the internet troll soul. Ask yourself this question: If I couldn’t take a single photo, would I still want to go there? If the answer isn’t a big fat yes, keep looking.

Question 5: What resources and support exist for this destination?

This one is a little less touchy-feely, but it might be the biggest question you need to answer. What information is available about this destination? Are there guidebooks, blogs, forums? Can I find maps for trails or cities? Are there tour companies operating there? (Even if you’re not booking a tour, their existence signals infrastructure and can help with planning logistics.)

I’m working on a South Korea temple-to-temple hike for next year (a personal one), and I’ve found some great resources through both official tourism sites and women’s hiking communities. That information makes me confident I can plan this independently, which is nice because my Korean lessons aren’t going so well. Is it really this hard to learn a language in your 50s, or is it just me?

Also, consider what support exists if something goes wrong. Is there cell coverage? Are there other hikers on the trail? What’s the emergency response like? Not that you’ll need it, you badass, but it’s good to be prepared.

Now what?

If you’re still thinking “okay, but I still don’t know where to go,” that’s actually perfect. These questions are meant to clarify what matters to you, not provide the answer. Sadly, the wheel of vacation destinations hasn’t been invented yet.

Grab a notebook (or my free Destination Research Planner if you want a structured approach) and start writing out your answers. You’ll see a pattern. 

Maybe you’ll realize you actually want to hike a beautiful European destination where warm meals and hot showers end your day. Or maybe the mountains are calling and you want something a bit more challenging. The point is you have options, but you have to figure out which options work best for you.

Your answers to these questions will point you toward destinations that fit your specific needs and nervous system—not some generic “best solo hiking” list. And that’s the whole point, isn’t it?

If you want a little more help working through these questions, you can grab my Fork it! I’m going solo! coaching session. We’ll dig into your answers together and create a concrete plan that builds your confidence rather than your anxiety.

But for now, start with these five questions. Write them down. Answer honestly. And watch your destination come into focus