I remember sitting in a café in London, staring at a map of the Greek islands, my finger tracing the ferry routes between Santorini and Naxos. The idea felt both electric and terrifying. I had no one to check with, no one to coordinate schedules with, no one to say, “Are we sure about this?” That was the moment I realized solo travel doesn’t start when you board the plane. It starts when you stop waiting for permission.
Over the years, I’ve learned that the hardest part of going solo isn’t the loneliness or the logistics. It’s the mental clutter — the endless “what ifs” and the feeling that you need a perfect plan before you can begin. So I stripped it down to four steps. Not a checklist of fifty things to buy, not a spreadsheet of backup routes. Just four honest steps that turned my hesitation into a ticket, and then into a life.
Step One: Choose One Thing You Want to Feel
Before you pick a destination, pick a feeling. Do you want to feel small and humbled by a vast landscape? Do you want to feel the quiet hum of a city where no one knows your name? Do you want to feel your own strength after hiking up a coastal trail alone?
This is the step most guides skip. They ask you about budget, about safety ratings, about the best time to visit. But the real question is emotional. When I planned my first solo trip to Greece, I didn’t start with islands. I started with the feeling I wanted: the sensation of being anonymous yet welcome, of walking through whitewashed streets without a schedule. That led me to Santorini — not the crowded sunset spots, but the quieter corners I later wrote about in Beyond the Blue Domes: A Solo Traveler's Guide to Santorini's Quiet Corners. The feeling came first; the place followed.
Write down three feelings you want from your trip. Maybe it’s “peace,” “adventure,” or “connection.” Then let those words filter your destination choices. A beach town in low season feels different from a bustling capital. Both are valid — but only one matches your feeling.
Step Two: Set a Container, Not a Script
The biggest mistake new solo travelers make is overplanning. They book every night’s accommodation, every train ticket, every museum slot. Then they arrive exhausted, following a script written by someone who didn’t know how jet-lagged they’d be on day two.
Instead, set a container. Decide your start date, your end date, and your first two nights of accommodation. That’s it. The container gives you structure; the empty space inside gives you freedom.
For my first solo trip, I booked a flight to Athens and a room in a quiet guesthouse for three nights. I had no plan beyond that. On day two, I met a woman at a bakery who told me about a tiny village in the Peloponnese. I changed my entire route because of that conversation. If I had pre-booked everything, I would have missed the best part of the journey.
If the idea of no plan makes you anxious, pick one “anchor” activity per destination — a cooking class, a guided walk, a ferry to one specific beach. Let everything else unfold. The anchor gives you a reason to be there; the empty afternoons give you space to stumble into something real.
Step Three: Pack for Your Actual Day, Not Your Fantasy Day
We all have a fantasy version of ourselves who wakes at dawn, does yoga on the balcony, hikes for four hours, then changes into a linen dress for a sunset dinner. That version exists in your imagination. The real version — the one who will actually take this trip — might sleep in, spill coffee on her shirt, and want to wear the same comfortable trousers three days in a row.
Pack for the real person. That means one versatile pair of shoes that you’ve already broken in, layers that work across temperatures, and a single “nice” outfit that doesn’t wrinkle easily. Everything else is optional.
I once packed a silk blouse for a solo trip to Kefalonia. I never wore it. Instead, I lived in a linen shirt and hiking sandals, walking the northern beaches for hours. Those beaches — the ones that felt like they belonged only to me — are the subject of Kefalonia's Northern Beaches: A Solo Traveler's Personal Guide, and I needed nothing fancy to enjoy them.
Here’s a practical rule: lay out everything you think you need. Then remove half. You will not miss it. You will thank yourself every time you lift your bag onto a train rack.
Step Four: Plan for One Moment of Discomfort
Solo travel is not a constant highlight reel. There will be a moment — maybe on the second evening, maybe halfway through — when you feel lonely, or lost, or stupid for not knowing the local customs. That moment is not a sign that you made a mistake. It is a sign that you are doing it right.
Instead of pretending it won’t happen, plan for it. Choose one small ritual that anchors you when the discomfort arrives. It could be buying a postcard and writing it to yourself. It could be finding a café with a good view and ordering the same drink two days in a row. It could be calling a friend for exactly ten minutes, no more.
On my first solo trip, I had a moment in a small port town where the ferry was delayed and I didn’t speak the language. I sat on a bench, ate a peach, and watched the fishermen untangle their nets. After twenty minutes, the discomfort passed. I still remember that peach. It tasted like the first time I realized I could handle uncertainty.
If you know that a tough moment will come, you can welcome it instead of fearing it. You can say to yourself: “Ah, here it is. I was ready for this.”
One More Thing: The Permission Slip
Before you buy the ticket, write yourself a permission slip. Not a packing list. Not a budget. A sentence that says: “I give myself permission to change my mind, to rest when I’m tired, to leave a place that doesn’t feel right, and to enjoy this exactly as I am.”
Fold that slip of paper and put it in your bag. Read it on the plane. Read it on the night you feel unsure. It will matter more than any guidebook.
And then go. The first step is never the flight. It’s the decision that your own company is enough — and that the world is waiting for you to show up, exactly as you are.
