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What I Wish I'd Known About Solo Travel Before My First Trip

  • Writer: Casey
    Casey
  • 7 days ago
  • 8 min read

I remember my first true solo trip. I'm not talking about a work trip where you just happen to be getting on a plane by yourself, and I'm also not talking about an overnight on the road to see someone a few hours away. Nope, I'm talking the good old totally-on-your-own-without-a-plan-or-responsibilities kind of solo trip. The kind you take when the whole point is to be....well, solo.


Whenever I say I'm traveling solo on an upcoming trip, I generally get one of two reactions. The first is something along the lines of, "have fun, enjoy it!" and is far more rare. More often than not, it's more like...."I could never do that. You're so brave." etc. etc. etc.


At this point, having traveled solo more often than not, I find it amusing....but I also get it. My first time solo was nothing short of incredible, but it was also miserable.


I'd gone to Aruba as part of their travel advisor training incentive, and even though I'd set up a handful of resort site visits, the majority of the trip was whatever I wanted it to be. I rented a jeep one day, bouncing around in Arikok National Park for 3 hours, sweating zinc sunscreen everywhere and generally hating my life, I melted down in a parking lot because I couldn't get the top of the jeep back up. Eventually I got myself under control, climbed up on the seat, and manhandled that beast like the badass I was but absolutely didn't believe. It was a moment that turned the trip around for me, honestly.


Said Jeep. She was a good girl, all things considered.
Said Jeep. She was a good girl, all things considered.

Until the next night when I woke up at 2am having a panic attack for no discernable reason. Sometimes it's just like that. So I called home, talked to someone who loved me, and decided the next day would be nothing but a beach day. It was, and the rest of the trip was fine, even enjoyable, but I learned a lot on that trip. And, on every trip since.


These days, very little rattles me the way it did in Aruba, because I've learned I can handle just about anything that comes my way. I've managed food poisoning, being lost, losing my passport, allergic reactions, horrible sunburns, packing mistakes and wardrobe malfunctions, catcalling, you name it. But because I was alone, I've also met incredible people, seen and done things I'd never heard of, walked streets and beaches and hiking trails with company, and gotten a table easily at a packed restaurant. It's a balance, and the more you travel solo, the more you learn - not just about traveling, but about yourself.


Considering your first solo trip? Here's what I wish I'd known that time in Aruba.


Solo Travel Isn't Lonely

Or isolating. The opposite in fact. For one thing, solo travelers tend to find each other. Being alone makes you more approachable, and it makes you more interesting. Plus, kindred spirits and all that. You don't even have to stay in hostels to meet other solo travelers, just pay attention when you're out and about. It's like there's an unspoken code, and the more you travel the more you'll pick up on who's solo traveling and who's a solo local. Sometimes it matters, often it doesn't.


And it's not just solo travelers you'll meet and get on with. I've had couples, families, and groups of friends adopt me. People often worry about the solo traveler, whether they're having a good time, whether they're ok. You are, but it never stops being lovely to be cared for. Lean into it. There's a nice acceptance that comes with knowing you can be on your own, but that you don't have to be.


This lovely soul and his wife were doing the same DIY Norway in a Nutshell tour. We spent the whole journey tag-teaming trains, ferries, and buses. When we arrived in Flam, I invited them to hike with me. His wife declined, so we took this photo to prove to her we'd made it to the top!
This lovely soul and his wife were doing the same DIY Norway in a Nutshell tour. We spent the whole journey tag-teaming trains, ferries, and buses. When we arrived in Flam, I invited them to hike with me. His wife declined, so we took this photo to prove to her we'd made it to the top!

Book Tours for the Logistics

Traveling by yourself is incredible for the freedom, and also super overwhelming at times. A lot of things are easy enough to do on your own, but a lot of things are genuinely better with others taking care of the planning. Book the tour, especially if it's an all-day thing, you're feeling lonely, or you simply just don't feel like dealing with it. There's a lot of pressure online to be an "independent queen" when you're solo traveling, and I call bullshit. You don't get a prize for being the person who never needs help. You get a prize for being the person who makes smart decisions, and saving your mental bandwidth is making a smart decision. Which brings me to my next point....


Decision Fatigue Is Real

This one still gets me, even 10+ solo trips later. The sheer number of micro-decisions you'll make as a solo traveler is staggering. Everything from where to eat to what to wear to which train to take. It wears on you FAST. This is one of the worst things about being on your own, and something nobody prepares you for.


You can't really avoid decision fatigue. Even if you've planned every day of your trip, there will still be things you'll have to adjust to in the moment, and I can almost guarantee you'll reach a point where you're just done. Those moments feel paralyzing, and honestly, the thing that helps the most is letting go. Letting go of the expectations you're placing on yourself to have the perfect trip, to choose the perfect meal/tour/hotel, to optimize your time. When you hit that wall, stop. Eat McDonald's (seriously). Watch a movie in your hotel room. Sit on a park bench. Ask someone for a recommendation....and take it. Put your phone down. Breathe.


Night 3 of my Portugal trip. I'd just arrived in Porto, and I was done. McDonald's it was. (I realized later, this was my Thanksgiving. Absolutely zero regrets.)
Night 3 of my Portugal trip. I'd just arrived in Porto, and I was done. McDonald's it was. (I realized later, this was my Thanksgiving. Absolutely zero regrets.)

Expect - but Don't Accept - the Single Tax

This one took me longer than I'd like to admit to come around to, and to start doing something about. Often, being solo is a boon - you can usually grab a spot at the bar, there's generally no wait for dinner, and you can snag the last spot on a tour. But sometimes, being solo means you're easy to stuff in a corner next to the kitchen, or you're shifted onto a different tour because of capacity, or you're given the bitch seat in the tour bus. You don't have to take it, friends. Just because you're alone doesn't mean you don't deserve a table with a view, so if you want it, ask for it. Don't be a jerk about it, but a simple, "can I sit here please?" will go a long way. It's not intentional so don't take it personally. Just ask.


Another trick? Pay attention to the people around you. Once in Norway in a crowded pub, I noticed another girl who appeared to be on her own. I said hello, asked if she wanted to share a table. She said yes, and we were seated much faster than if we'd both waited for our own thing. It turned into a lovely evening, we never saw each other again, and it was fine. In Austria once, a server assumed the gentleman in front of me was my father and offered us a table. We both shrugged, and enjoyed a lovely coffee together.


Enjoying the tasting menu with my new friend in Flam.
Enjoying the tasting menu with my new friend in Flam.

Put the Phone Away

If I could shout this from the rooftops, I would. Put the damn phone down. For one thing, you'll notice more. For another, your battery will last longer. And, you'll truly be present and experience your destination. You can scroll social media at home.


Whenever I say this, people usually come back with, "but what do I do at a restaurant?" Simple. Take a book, or a journal, or (gasp) just sit there. I promise, nobody is paying attention to you, and if they are, they're probably going to think you look super confident and composed. Think about it - when you see someone alone, is your first reaction that they must be miserable? Unlikely.


Personally, I take my travel journal with me. It's become my little ritual, to write in the evenings or during my downtime. It's a conversation starter - people will ask what you're working on, or if they're also solo, they'll recognize you're capturing your thoughts and it's the easiest opening ever. The flip side of this is that if you do actually want to be left alone, plant your nose in your phone or your computer. People will get the hint.


Journaling in Zagreb, Croatia
Journaling in Zagreb, Croatia

If You Get Lonely.....Talk

Seriously. I know, I know, people are scary and you're an introvert and blah blah blah. People are people everywhere, the majority are not trying to rob or scam you, and as we've already discussed, nobody is judging you for being alone.


So if you find yourself needing someone to talk to, take a deep breath and open your mouth. Ask if they're local or traveling, or where they're from. Ask what fun thing they did that day. Ask about their favorite restaurant, book, bar, musician, sports team, whatever. Ask if they speak your language. And then, talk. Tell them you're far from home and missing your dog, cat, person, whoever. You don't have to tell them alone - in fact, most people will tell you not to (your call) - or where you're staying. But I've truly found that the vast majority of people are curious and kind. So be curious and kind back.


I'll never forget Fern, a Thai university student who happened to be on holiday on the island I was diving on. She heard me talking to the bartender, and shyly asked if we could chat so she could practice her English. We talked for 2 hours, and it was delightfully wholesome. At the end, she thanked me and said "people are people everywhere." It's stuck with me ever since. You're truly only alone traveling if you want to be.


I don't have a photo of Fern, but this story was just as meaningful. At Badwater Basin in Death Valley, I briefly chatted with Ben from Australia. We found ourselves following the same route, so by the time we made it to Artist's Pallett we were fast friends. We shared the wonders of the landscapes together, then went our separate ways. It was what we both needed - just a few moments of shared experience.
I don't have a photo of Fern, but this story was just as meaningful. At Badwater Basin in Death Valley, I briefly chatted with Ben from Australia. We found ourselves following the same route, so by the time we made it to Artist's Pallett we were fast friends. We shared the wonders of the landscapes together, then went our separate ways. It was what we both needed - just a few moments of shared experience.

Something Will Go Wrong

This is the nature of traveling, but it's even more true when you're by yourself. It's just part of it. Something will go wrong, and you'll have to deal with it. YOU CAN DEAL WITH IT. And the best part? You don't actually have to deal with it on your own. Call someone back home. Talk to your hotel. Get help, vent, cry, whatever. Whether it's something major or minor, it can be fixed, and you'll figure it out. And when you do, you'll feel like a badass.


I'd just spent 48 hours in my room with food poisoning, and still had 4 days left in Thailand. This was the day I managed to leave the room - dehydrated, exhausted, hungry but not interested in food. I drank a fruit smoothie and sat in the shade until I felt human again.
I'd just spent 48 hours in my room with food poisoning, and still had 4 days left in Thailand. This was the day I managed to leave the room - dehydrated, exhausted, hungry but not interested in food. I drank a fruit smoothie and sat in the shade until I felt human again.

You Will Question Everything You Know About Yourself

Unless you've spent a lot of time solo, you're going to go through the 5 phases of solo travel. Elation. Terror. Crippling insecurity. Questioning. Acceptance. And then all of them all over again, because that's how it goes. Solo travel is often a roller coaster of emotions, and there's not really a way to avoid or escape it. You just have to go through it.


You Will Wish You'd Done it Sooner

Even with the shitty moments. Even with the things that go wrong, the bad experiences, the decision fatigue, the anxiety. You'll make it through the trip and realize the only thing holding you back all this time was YOU. That your first solo trip opens up a world of possibility. That you don't actually need someone to go with you, that you're just fine on your own. Sure, it's often better to experience a wonder with someone.....but you learn that strangers can be just as great companions, and you eventually learn that yeah, you can actually come back someday. You have the rest of your life to travel, and no one knows what that's going to look like. All we can do is take the opportunities in front of us, and if that means going solo, so be it.


To this day, one of my favorite photos. It's dark, there's a finger in the frame, and it's off center. But this moment signifiies so much - joy, hope, peace, freedom.
To this day, one of my favorite photos. It's dark, there's a finger in the frame, and it's off center. But this moment signifiies so much - joy, hope, peace, freedom.

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