What Nobody Tells You Before Your First Solo Trip (But Should)
“The more I traveled, the more I realized that fear makes strangers of people who should be friends.” - Shirley MacLaine
I was sitting at a table for one in a restaurant I'd chosen entirely by myself, in a city I'd navigated entirely by myself, on a trip I'd planned entirely by myself, and I felt completely, unexpectedly overwhelmed.
Not in a bad way. Not in a good way either, really. Just in a deep way that nobody had prepared me for.
Everyone told me my first solo trip would change my life. What they didn't tell me was what that actually looks like on a Tuesday night when you're a little tired, a little proud, and very much alone with your thoughts and a menu you can't fully read.
This post is what I wish I'd had before I left. Not a packing list, you've got Google for that. The real stuff. The emotional and practical things that catch first-time solo travelers off guard.
The Freedom Is Real, And So Is the Exhaustion
Here's the thing nobody mentions about having total freedom: it's a lot of work.
When you travel with someone else, decisions get shared. What to eat, which way to walk, whether to push through to one more museum or call it a day. You negotiate, you compromise, you hand the mental load back and forth. Solo? Every single choice is yours. All day. Every day. Similarly to being single and living by yourself. But we’ll save that post for another day.
For the first day or two, that feels incredible. By day three or four, something shifts. The joy of "I can do whatever I want" starts quietly competing with "I have to decide everything." Researchers call this decision fatigue, and it's real. Even small decisions start to feel heavier than they should.
The fix isn't to over-plan your trip. It's to expect this and be kind to yourself when it happens. Give yourself a morning with absolutely no agenda. Let the afternoon be unstructured. Build breathing room into your itinerary, especially on longer trips. Solo travel isn't just physically tiring, it's mentally full in a way that group travel simply isn't.
The Loneliness Won't Be What You Expect
Most people going into their first solo trip are braced for loneliness. Some even brace for a bit of boredom. What they're not braced for is the specific kind of loneliness that shows up.
It's not the loneliness of having no one around. Cities are full of people. Restaurants and bars are social. You'll talk to strangers more in a week of solo travel than in a month of normal life.
The loneliness that catches you is this: standing in front of something so beautiful, a view, a meal, a moment, and having no one to turn to and say, “Are you seeing this?”
That's a different feeling and it definitely passes. However, knowing it's coming makes it easier to sit with when it does.
What I've learned: Lean into connection rather than fighting solitude. Book a group day tour for your first or second full day. You get structure, company, and local knowledge without surrendering your independence. I personally love booking walking food tours in a new city. When you go out to eat, sit at the bar or the counter instead of a corner table. Say yes to the conversation the person next to you is trying to have or strike one up with the waiter or bartender. Research consistently shows that most solo travelers actively want to meet people. I tend to tell myself that isn’t true, since when I am home, I can be a true homebody. However, the fact remains that I make new friends every time I travel, especially when I’m solo. We solo travelers have just traded the obligation of group travel for the choice of when and how.
It Costs More Than You Think
I don't love being the one to say this, but solo travel is more expensive than the influencer math suggests. Single and living alone? Same energy.
Hotel rooms cost the same whether one person or two is sleeping in them. Taxis, tours, and rental cars are often priced per group, not per person. Nobody's splitting the Airbnb with you and those "group discount" deals that make certain experiences affordable? Not for you.
On my first trip to Barcelona I tried to convince every paella restaurant I found to let me have a paella for one. They weren’t having it and all said, “Sorry, it’s not possible.” It wasn’t until my fourth solo trip to the city that I learned enough Spanish and put on enough charm to make my dream of a beachside paella for one possible.
Reframing the experience actually helped me. When you travel alone, you also spend only on what you want… what you really want. No compromising the restaurant choice to suit someone else's budget. No splitting your cash on the excursion nobody really wanted but someone suggested. Your money goes exactly where you choose. Everything feels worth it when you know you are doing things you enjoy.
Budget for solo travel the way it actually works, as a single-occupancy, full-autonomy experience, and you won't feel blindsided.
Eating Alone Feels Weird Until It Really Doesn't
The table for one is one of the most universally dreaded parts of a first solo trip. I won't pretend otherwise.
I still have an aversion to eating by myself even in my home city and on domestic business trips, you’ll find me at the counter or ordering room service if a friend isn’t in town.
You walk into a restaurant, ask for a table for one, and something in you braces for... what, exactly? Pity? Stares? Someone coming over to check if you're okay?
Here's what actually happens: Nothing. The waiter seats you. People eat their food. Everyone goes about their evening. The whole performance (the embarrassment, the self-consciousness) is playing entirely in your own head.
A few things that help: Ask for a counter seat or a bar stool if the restaurant has one. Go slightly off-peak so the room is less intense. Bring a book, not because you'll necessarily use it, but because having it takes the edge off if you are truly worried. These days I find myself scrolling through the pictures I’ve taken. Order exactly what you want, because you don't have to share.
Now, as the paella story shows, some dishes and experiences just aren't designed for one (Korean BBQ, for example). But with solo travel growing the way it is, more and more restaurants are adapting.
Most solo traveler friends say dining alone becomes one of their favorite parts of the trip. I believe them now. I didn't before I'd done it several times myself. One year I slow-traveled in Mexico, and I went to Pujol in Mexico City for my birthday. To this day, sitting at the bar, taking in the atmosphere, and being looked after by genuinely warm staff is one of the best solo experiences of my life. From the cactus aguachile with margarita scallops to the 3,484 day aged mole, every bite was perfection.
Your Safety Instincts Are Your Best Tool
Safety is the thing that stops more people from taking their first solo trip than anything else, especially women. That fear is valid. It's also worth naming clearly: The vast majority of solo travel is safe. And the travelers who feel safest aren't the ones who are fearless. They're the ones who were prepared.
A few things that make the biggest difference for me:
Arrive in daylight. Book your transport so you reach your destination before dark, especially on trip one. Navigating an unfamiliar city for the first time at night is stressful in a way that's easy to avoid.
Share your itinerary. Send someone at home your accommodation names, flight numbers, and a rough daily plan. Check in regularly. It takes five minutes and gives both of you peace of mind.
Trust your gut without needing proof. If a situation feels off, you don't need to justify leaving. You don't owe anyone an explanation. Just go. This applies everywhere, not just when you’re traveling solo.
Have a backup of the essentials. Write your hotel address and key contact numbers in a notebook. Phones get lost, stolen, and run out of battery. A notebook doesn't.
Tibidabo
The Moment That Changed Everything
My first truly solo trip was to Barcelona. I had been to the city before, but not by myself. The first time was not a good experience. This was my first trip post-divorce. I decided to go there to live my own experience and see how brave I could be on my own. Would I take the train? Would I confidently get in the taxi? Would I panic when asked a question? Could I stay in the Airbnb with no one to translate if something went wrong? It was all a resounding yes! There was a day when I even made a video for my future self so that she would remember that feeling. The overwhelming happiness of knowing you will be just fine, if you just trust yourself.
That moment is why people go back. It's why "my first solo trip" is a story people tell for years. It's the thing nobody can prepare you for, not because it's a surprise, but because it's yours.
Before You Go: The Things That Actually Matter
Book accommodation in a central, walkable area for trip one. Pay extra for location. You'll thank yourself at 10 pm when walking around.
Arrive in daylight. Non-negotiable.
Pack light enough to carry your bag yourself for 20 minutes. No one is helping you with your luggage. Not all hills are created equal. Looking at you, Lisbon.
Write your hotel address and key numbers in a notebook. Don't rely solely on your phone.
Research local transport before you land. Know whether ride-share apps work there, whether taxis need to be negotiated, and what the airport transfer options are.
Share your itinerary with one person at home.
Build in one or two buffer days: no plans, no pressure. Especially on trips longer than five days.
Solo travel will surprise you. It'll probably unsettle you a little, at some point and if you let it, it'll show you something about yourself that you couldn't have found any other way.
Don’t be afraid. Go. Just go prepared, and honest with yourself about what you're walking into.
Have you taken a solo trip? Tell me in the comments. What surprised you most?
If you want the full story and some other anecdotes, watch the vlog below. I get into the moment that changed everything for me.
