Most “how to plan your first solo trip” posts are basically a packing list with extra steps.

Book flights. Book hotels. Buy insurance. Pack a personal safety alarm…

Sure, it’s all useful stuff to know – and a part of the process.

But none of it touches the actual thing keeping you stuck, which is emotional, not logistical.

Because if you’re anything like I was before my own first solo trip, the problem was never “I need more information.”

(Let’s be real, you’ve probably already read all the travel blogs, found a few packing lists, and saved 50 destination reels and Pinterest pins!)

The problem is the fear that shows up the second you try to actually book something.

And I know, because I’ve been there. Done that.

I have anxiety and social anxiety, and I nearly talked myself out of my first solo trip at least 100 times before I even got through airport security!

But I felt scared and went anyway.

And in the 5+ years and 24 countries since, trial and error has turned into an actual system, that gets you from “I want to do this” to “my flights are booked”, one small step at a time, whatever your anxiety has to say about it.

I’ll walk you through the whole thing in this post, so let’s get into it!

This post is also a podcast episode! So if you’d rather listen than read, hit play below. It’s also on Apple Podcasts, Amazon Music and YouTube if you prefer those.

https://open.spotify.com/episode/6OLAhNlSPTMF2ILsAJdExN?si=N8F6lvywSq2wLPKv4mMU-g

Katie’s TL;DR

My Dream to Departure Roadmap has 7 stages, refined across 24 countries of genuinely doing this myself, and two techniques inside it do a lot of heavy lifting (I’ll share those below!)

The fastest proof that this works: My Street View Accommodation Hack. It’s free to use and has reduced my pre-trip anxiety more than almost anything else I do.

The complete system: If you want the full roadmap, worksheets, safety guides and Notion Solo Travel Planner behind everything in this post, that’s all inside the First Solo Trip Toolkit.

Haven’t joined my free course yet? Start with my 7 Days To Your First Solo Trip (Even If You’re Anxious) email course. It pairs perfectly with the toolkit!

Table of Contents

Why Generic Planning Advice Doesn’t Work When You’re Anxious

I didn’t realise this when I was considering my first solo trip, completely overwhelmed by fear, but most solo travel checklists have a hidden assumption:

That the only thing that stands between you and booking is more information.

So they hand you a list that says something like:

Book flights
Compare hotels
Buy insurance
Pack and go!

As if ticking every box just switches the fear off.

But if you have anxiety, like me, you already know that’s not how it works.

Because the real blocker stopping you from solo travel was never the logistics at all, but the emotional overwhelm sitting underneath them.

And that’s why a real system has to handle both of those things at once:

Not just the “what to do”, but the “how do I actually get myself to do it?!” too.

Katie’s Top Tip: If a “how to plan your first solo trip” guide or resource only gives you tasks and never touches the fear behind them, it’s only solving half the problem.

My 7-Stage Dream to Departure Roadmap

This is the exact sequence I still use for every single solo trip I take, even now, 5+ years and 24 countries in.

I call it my Dream to Departure Roadmap, and it’s built to work alongside your anxiety, not against it!

Here’s how it breaks down:

1. Dream

Gather inspiration and imagine the kind of trip you want (without trying to research every destination on earth first!) This stage is about possibility, not decisions.

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2. Decide

Commit to one destination and one set of dates. The trap here is waiting for your fear to disappear before you choose. It won’t. So you choose anyway.

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3. Book

Flights, accommodation, insurance. The goal is a good enough option, not the “perfect” one after weeks of overwhelming yourself comparing tiny details.

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4. Plan

Build a simple, loose itinerary. And nope, that doesn’t mean a minute-by-minute schedule that leaves no room to breathe or change your mind!

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5. Prepare

Sort your arrival plan (this is so underrated yet so important!), packing and safety essentials, so none of it gets left until the night before, when your anxiety has the least patience for it.

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6. Go

Follow your plan loosely, and give yourself full permission to change it. You’re supposed to actually enjoy your trip – not feel trapped into a plan that stopped working on day two.

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7. Reflect

Capture what you achieved, not just what went wrong. This is where the confidence for your next trip actually gets built.

If you want support putting my Dream to Departure Roadmap into action for your trip, every one of these stages is included inside the First Solo Trip Toolkit, so you’re never stuck wondering how to actually do the stage you’re on!

Katie’s Top Tip: You don’t need to feel ready for every stage before moving to the next one. You just need to complete enough of it to take the next step.

Me solo travelling on the Norway Coastal Express!

Now, ready for an exclusive teaser?

These two techniques are two of my favourites inside the Toolkit, just to give you a taste of what to expect!

The Technique That Changed Everything For Me: The “What If” Reframe

This is the tool that made the single biggest difference to how I plan every solo trip.

Basically, anxiety thrives on unanswered questions.

So instead of letting a “what if” spiral into 10 worse ones, you ask yourself 4 simple follow-up questions instead.

Here’s how it works, using one of the most common solo travel fears: “What if I get lost?”

Now, let’s reframe it in a way that is helpful to us:

What’s the realistic likelihood? Moderate. It’s completely normal to take a wrong turn in an unfamiliar place, especially somewhere new.

If it happened, what would I actually do? I’d stop walking, find a safe place to pause, and check my map. If I’m still not sure, I’d ask at a shop or tourist information point.

Who or what could help? Offline Google Maps, locals, tourist information centres.

What’s a more balanced way to think about this? Getting lost doesn’t mean I’m incapable of solo travel. It’s normal and can be overcome.

Notice how it doesn’t end with “and then the trip was ruined.” It ends with a plan.

And that’s the whole point.

Not proving nothing will go wrong (because that’s, sadly, impossible), but proving to yourself that if it does, you’re capable of handling it.

That’s how you turn anxiety into action.

Katie’s Top Tip: Naming the actual “what if” behind your fear (because there is always at least one!) shrinks it down to something manageable. Something you can act on instead of just feel.

I have a version of this exact reframe exercise for every fear on your list, worked through step by step, inside the toolkit’s Anxiety & Confidence Workbook.

So you’re never stuck reframing alone at 2am with a spiralling brain and no plan!

The Solo Travel Anxiety and Confidence Workbook

The Hack That Changes How You Choose Accommodation

This is something I do before every single solo trip: after I booked accommodation in Nice, France, which left me uncomfortable and caused my anxiety to spiral.

And I would say it’s reduced my pre-trip anxiety more than almost anything else!

I call it “walking” the neighbourhood before you even book, and it takes just 5 minutes.

Here’s exactly how:

Find the accommodation on Google Maps. Copy the address from your booking platform and paste it in, then zoom out to see the surrounding streets.
Drop into Street View. Drag the little Street View icon onto the road of your accommodation and take a virtual “walk” around the block.
Look for the signs that matter. Well-lit streets, a clear entrance, restaurants or shops nearby (that’s foot traffic), a route you’d feel fine walking after dark…
Make your decision. Everything look comfortable? Book it. Got doubts? Don’t be afraid to look somewhere else!

That’s it!

It may sound simple, but I’ve lost count of the accommodations I’ve cancelled because they didn’t pass the Street View test. And I’ve never once regretted it.

Katie’s Top Tip: If you feel off just walking the streets on Street View, you almost certainly won’t feel comfortable doing it in real life either.

The full Accommodation Safety Audit scores all of this for you automatically, and covers exactly what to check before, during and after you check in.

That’s inside the Solo Female Safety Toolkit, so you’re never just eyeballing it from a hotel’s (often highly glamourised and well-angled) marketing photos and hoping for the best!

The Tool That Ties It All Together

So you may be thinking “okay, this all sounds helpful. But how do I actually, practically use these exercises to plan my own solo trip?”

And this is honestly the part I love the most inside the Toolkit, because it turns the roadmap from a nice idea into something you can easily follow all the way to departure day!

The Guided Solo Travel Notion Planner.

So instead of switching between 15 different tabs, hundreds of screenshots and your notes app, everything lives in one dashboard.

Your bookings, your itinerary, your arrival plan, your packing list… all in one place!

It has a smart, one-click itinerary builder, so you’re not manually formatting a spreadsheet at 11pm (who has time for that?!)

And arrival day planning built right in, so you can navigate arguably the most stressful day of your solo trip with calm and organisation.

But my favourite part is the smart progress tracking, which always tells you what your one next step should be, so the “what should I even be doing right now?!” spiral just disappears.

This is the tool I wish I’d had when I was first planning my own solo trips.

(Which is why I spent years and a lot of trial-and-error perfecting it so I had the perfect system for my own trips.)

And genuinely, it would have saved me SO much overwhelm – and probably a fair few of those 100 talk-myself-out-of-it moments too!

Katie’s Top Tip: Solo travel overwhelm usually isn’t about having too much to do. It’s about not knowing what to do right now. Fix that, and everything else gets so much easier.

What’s Actually Inside The First Solo Trip Toolkit

Here’s a peek at what you actually get when you’re ready for the full system, rather than just this taster:

The Guided Notion Solo Travel Planner – your travel planner, itinerary builder and progress tracker, all in one place.
The First Solo Trip Starter Pack – the full Dream to Departure Roadmap, checklists and a first-day worksheet, so you always know your next step.
The Solo Female Safety Toolkit – my complete solo safety system, including the Accommodation Safety Audit you just had a taste of above.
The Anxiety & Confidence Workbook – every “what if” reframe, and every fear worked through properly, not just the one example above.
The Europe Destination Database + Decider – choose a destination that actually suits you (without another 3 hours of Googling!)

Plus, there’s a bonus curated Solo Travel Resource Vault thrown in, all my trusted tools and recommendations in one place, so you’re never left wondering what to actually use!

But most importantly, it’s about not having to spend the years I did building all of this yourself, from scratch, while you’re already anxious about the trip itself.

I WANT THE FULL TOOLKIT!

Why Solo Travel Isn’t Something to Save for “One Day”

I’m not going to tell you there’s a countdown clock on solo travel, because there really isn’t.

I wholeheartedly believe that solo travel is for all ages.

But I do want to be honest and say that, in my experience, waiting doesn’t actually make you more ready.

Instead, I’ve found that whenever I’ve waited for the “right moment”, it’s always just given my overthinking more time to talk me out of it.

I mean, when I was considering my first solo trip, to Montreux in Switzerland, I stalked the hotel’s website for an entire month, too scared to book.

And by the time I finally did, the price had gone up!

Don’t get me wrong, the First Solo Trip Toolkit doesn’t remove the fear entirely. (Nothing genuinely does, not even for me, 24 countries in.)

But what it does remove is the guessing.

And I also want you to know that your fear isn’t a personal flaw.

Shame for feeling afraid never moved anyone closer to booking that flight.

But what actually does help is turning that fear into something tangible you can name and work through, rather than one huge, nameless feeling we just call anxiety.

And for ages before my first trip, even the idea of naming my own fears felt overwhelming.

It just felt like fear, full stop. Nothing else.

So that’s exactly why I spent 5 years trialling and refining the process behind the Anxiety & Confidence Workbook, so you don’t have to work out how to get to the root of your fear alone.

I’ve already done that part for you!

Katie’s Top Tip: A tangible “what if” is so much easier to work through than a nameless feeling of fear. Naming it is the first step to actually solving it.

Is This Right for You?