What I Wish I Knew About Traveling Solo

I absolutely LOVE traveling solo. It’s a completely different type of Freedom that I never thought I would have. And that I never want to lose. It’s natural to become completely terrified before the adventure begins, but when you finally get there, after the terror milds, you get this moment of invincibility and power. A few of us travelers have come together to compose a list of things we wish we knew before traveling solo. Here are things we’ve learned, some insight, and some tips.

First, I’d like to introduce you to two amazing people that have collaborated on this post:

Chelsey, which you can catch her blog at The Devine Adventures, spent her childhood vacationing from Canada to the Caribbean. Later, she lived in Germany while on an exchange program, and fell in love with Europe. She believes the best experiences come from submersing yourself in new cultures and seeking the once-in-a-lifetime adventures each place has to offer. She loves a good German Liter of Beer and has an obsession with Ireland.

Joe was a late comer to the international travel scene, not getting his first passport until he was 23. Originally from NJ, before traveling internationally he’d explored the US by way of MLB ballpark trips, but after his first trip to Toronto in 2013, was hooked on international travel. Since then he’s been to nearly a dozen countries in the Americas, Europe, and Asia, with no signs of slowing down anytime soon, all while continuing his quest to visit all 30 active MLB stadiums.


1. There is  a difference between Domestic and International travel.

This is probably the number one thing I wish I knew before my first trip to Europe. I’d been all over the US and Canada by then, and I wasn’t really prepared for how shocking being abroad can be. We take a lot of things for granted in this country that isn’t the case abroad. Even little things like buying allergy medicine can suddenly feel daunting abroad. Just stay calm, but remember to budget a little extra time in case things aren’t as easy as you expect.

2. Dress nice to fly

You’d be surprised how much better you get treated on an airplane if you look like you tried a little bit. Comb your hair. Skip the sweatpants (jeans are fine) and maybe wear a collar. I usually wear a blazer from Uni Qlo in case I get cold, but it also dresses up the look a lot. This usually makes the customs process go a touch more quickly as well. (And if you’re lucky enough, you can even get bumped to First or Business Class!)


Something will, inevitably, go wrong on your trip. Your bags could get lost by the airline. A train could get cancelled. You could get food poisoning (see number two). But you know what? Chances are, you’re going to survive. Just breathe. I remember my first time traveling in Europe the airline (United) lost my bags (this is before I started carry-on only) and I basically spent an entire day in London freaking myself out about where my stuff was, instead of just working through the issue, stopping at an H&M, and enjoying my trip. Just relax. Grab a cup of coffee and people watch for a bit. Everything is going to be okay.

4. You’ll probably get sick

Depending how long you’re away, you’ll probably, at one point or another, get sick. Especially if you love street food like I do (pop a herring in Amsterdam or try a Currywurst in Berlin!) And when it inevitably does happen, do not be afraid to spend a day in the hotel/hostel/AirBnB if you need it. Other times, it’s the weirdest things that cure you. I was sick for a week in France before I went to a Mickey Dees. And what do you know, after that, I felt fine!

5.  Be very careful in your packing

Someone won’t have what you may need, because you’re not going with anyone. Make sure you have a checklist of things you may need. If you don’t, you may either have to learn to live without it, or try to find it in country (depending on what, can be much more difficult than you think!).

6. You don’t need to pack an umbrella

Seriously, chances are you’re going to be in a city. Buy a €/£/$5 (¥500) one in a bodega and throw it out on your way to the airport. You’ll save a lot of space in your bag, and chances are you won’t need it.

7. Do not over pack

Chances are you’re going to want to bring a lot of souvenirs, gifts for friends and family, home with you. If your bag is already full when you leave, you can’t take much home. Or you stuff your bag so full, you can break it.

8. Try not to check a bag

This is something I discovered after losing my checked bag on my first flight to Europe. You should be able to go at least 10 days with just a backpack, more if you re-wear clothes or find a laundromat. I use the Osprey Farpoint 40 myself and I love it. Carryon size makes it ideal, but it still holds plenty for an extended stay.

9. You’re going to be spending a lot of time with you. I hope you like, you.

10. Take a familiar break

Yes, we all love traveling, but sometimes it’s good to take a mental break from the culture shock for a bit, especially when you’re abroad long-term. See an American movie, eat a cheeseburger, hell, go see a baseball game, but whatever you do, do something to relax your mind for a few hours. It’s amazing how much more enjoyable a trip can be after just a little bit of normalcy to decompress. For me, I like to watch a movie or a little American TV at night before bed. Sometimes it’s as little as ten minutes, but it helps to not have to think for a bit.

11.You will miss familiar conversation

Meeting new people is amazing, especially when you’re on vacation. As a solo traveler, chances are you will meet copious amounts of new and awesome people. But, at some point, you will crave familiarity – just wanting make an off the cuff comment about something that you saw or did that doesn’t require you explaining yourself or giving them a backstory as to why you’re pointing it out.

12. It is awesome to do what you want when you want

There really is nothing like waking up when you want to, eating where you want to, seeing what you want to, and leaving when you want to. You get this odd sense of power when you realize you don’t have to make sure your plans are conducive to another person or group.

13. There will not always be someone to bounce ideas off of

On the contrary to my previous point, it can get overwhelming some days to make every choice. I’m the kind of person who likes to ask peoples’ opinion for things – “Do you think this or this would be better?” “Fish or boxty?” When you’re used to this kind of back and forth decision making, it can be difficult some days to make the choices for yourself. There were several times during my first solo trip when I just wanted someone to say “we are going here and doing this today”.

14. Follow your interests

One of the best things I’ve ever done while traveling was taking a James Bond themed tour in London. It was incredible. And it was full of fellow Bond-lovers. It was a great way to meet people with similar interests, and see parts of London I might never have gotten to otherwise. In Chicago, my buddy Kyle and I did a self-guided tour of John Hughes film locations, and we had entirely too much fun pretending we were Ferris and Cameron on their day off. I’ve done WWII themed tours as well where I had great discussions with people I still keep in touch with. The point is – do what interests you. There’s no need for debate with other travelers. The trip is what you make of it, and a great way to maximize that is to combine two things you love.

For example, I’ve been to 16 active MLB ballparks, but one of the craziest experiences was seeing the Tokyo Giants play the Hiroshima Carp at the Tokyo Dome. Watching the difference in how two cultures treat the same game was fascinating. And eating Sushi at a baseball game is an experience I won’t soon forget!

15. You need to have a sense of direction

Or at least be able to read a map. That helps you with subway, trains, and bus maps. It also helps with finding your way around the city, and back “home”.  Especially if you don’t have phone service.

  • Google Maps is your friend, but a fickle mistress – When traveling solo, getting around a city you are not familiar with can be a task in and of itself. What a day we live in when you can get turn by turn directions just about everywhere you go. Ahhh, google maps, how I love you so! But don’t be caught without a backup physical map! When Google Maps decides not to work in the middle of directing you to your final destination, you do NOT want to be caught with no alternative.

16. You are in charge of your safety

Be very careful about what you say, what you do (especially drinking), what you flash (ex. Rolex, Money, MK Purse, $600 high heels–even if they’re just really good knockoffs.).

17. You have to pay attention to your surroundings and your things!

There are professional pick pockets everywhere you go. Keep your purse zipped. Even keep your hand over it. My roommate in France put her cell phone in her pocket for two seconds and it was gone. She also had her iPad stolen on a train when she got distracted for a moment. Those people who come and ask you to sign a petition and/or donate/give money. They work in teams. One distracts, one steals! Wave them away, but keep your things tight!

18. Trust your instincts

If you have a bad feeling, trust it. But don’t confuse the good instincts from preventing you from having an amazing time, and not letting you meet new people.

19. You will feel invincible

You well get a rush of being adventurous. You will realize that everything that’s happened in your life has lead you this. You will feel as if nothing can stop you! Use this feeling to motivate you, to try something new, to meet someone new, to strike up a conversation with that guy/girl on the dance floor, to ask that person out for coffee that you’ve seen every day on your commute, to test your strengths. But never forget to be safe!

20. Don’t be afraid to be honest with yourself

I HATE hostels. Absolutely fricking hate them. And you know what? When I’m on my own, I don’t have to listen to people who think that’s a better way to stay. So I’ll take my hotel, or my AirBnB on my own. Honestly, this freedom – to decide what you want to spend, and what is acceptable for a night- is one of the greatest things about traveling alone. I’m also the type of person who never had an interest in Paris. But Normandy was somewhere I’ve long dreamed of visiting. So last summer I spent one night in Paris, and a week in Normandy – something a lot of people would think was nuts. But I loved it – and I didn’t have to answer to anyone about it. Sure, friends and family might question you deciding to spend a week in the Italian countryside rather than Florence, but if that makes you happy, their opinions don’t matter.

21. Eating alone is just as awkward as you thought it was

It is inevitable that while you are traveling solo, you will also be eating solo. I was so worried about this fact before I went on my first solo trip – and it wasn’t completely unwarranted. Most people really do not care if you are alone at a table. No one will snicker or talk about your sad, lonely self under their breath, but getting over that odd social phobia (maybe it’s an American thing? Not sure) can be difficult. It’s awkward. It feels wrong. But you gotta eat!

22. Learn the culture of where you’re going

This can help you prevent incidents. Smiling at strangers on the street is considered suspicious and makes you look *simple*. Or the Peace Sign hand gesture is considered as “the middle finger” in places such as Australia, Ireland, New Zealand, South Africa, and the UK.

23. Learn some words in the country’s language

This will help you, and everyone. Plus, it shows that you’re trying to integrate, and not just be a tourist. Words such as “Train Station”, “Airport”, “Help”, “Ambulance”, “Bathroom”, “Leave me alone”, even “Do you speak English?”, the names of food, especially foods you don’t like or are allergic too, and some directions. Not everyone speaks English—don’t assume that they do.

24. Talk with locals

Practice some of the phrases you’ve learned. Make some friends.

25. People will assume you are super outgoing

When people find out you’re traveling solo, they seem to think you are good at walking up to strangers and striking a conversation. It’s super awkward when you are not, in fact, that person (cue the massive thumbs pointing to this girl right here).

26. Don’t be afraid to ask for help

This may be a guy thing, but I know a lot of people who won’t ask for help when the need it. Even if you don’t speak the language, people will do their best to help. Just try not to do it at rush hour! Just remember, when you’re in someone else’s city you’re the asshole tourist that gets in your way on the walk to the subway. Be polite, and look for someone who isn’t in a rush.

27. You will have learned what you are capable of.

28. You will learn more about yourself in those [two] weeks, than you have in your past [23] years.

29. Readjusting to normal life is hard

This is the case for just about any vacation, but particularly hard if you went on vacation alone and came back to living with other people. Being alone becomes the norm after a few travel days, so having other people in your “personal space” is oddly off-putting for a few days upon return. I found myself wishing people would stop asking me so many questions for about a week.

30. Once you return, you realize absolutely everything is the same, except you.

Categories: Adventure, Airline, Airplane, Bali, Beach, bucket list, Cuba, Featured, Food, Foodie, france, Germany, Hawaii, hiking, Italy, Las Vegas, life list, Outdoors, Packing, passport, Solo, Spontaneous, Sports, travel, Travel Solo, Uncategorized, United States, Weekend Trip

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