Best Tips: Lone Traveller Holidays

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I’ve done so much solo traveling over the last five years that I had to get a new passport because the old one was full of stamps. So as you can imagine, I get many questions about how to enjoy Lone Traveller Holidays from friends, strangers, and Internet Strangers alike. These questions range from “Where’s the best hotel in New York City?” to “What are some things to do in Lexington, Kentucky?” But the questions I am asked the most often are about how to travel alone.

“Don’t you get lonely?” people ask. “Don’t you get bored? Aren’t you afraid to eat in restaurants alone? Won’t people think you’re a weirdo with no friends? Isn’t it dangerous? Won’t you get murdered?”

Well in the past five years, I’ve traveled in over 50 countries as Lone Traveller Holidays, and I haven’t been murdered even once. So I figured it was high time to share my wisdom about how to travel alone with you, Internet Strangers. Lone Traveller Holidays are awesome, and anyone can enjoy them. Just follow these basic steps.

Lone Traveller Holidays: THE EIGHT STEPS

Lone Traveller Holidays
1) go to a restaurant alone

Before you can know how to enjoy Lone Traveller Holidays, it’s better to start with a small step. Take yourself out to a restaurant in your hometown. Do not let anyone else come with you, no matter how much you cry. There is no restaurant too casual or too fancy to use as practice.

In this photo above, you can see me dining alone at Alinea, which is a three-star Michelin restaurant in Chicago. I had a blast chatting with the waiters, and I even made friends with the couple sitting next to me as we tried to solve the menu. (At Alinea, the menu is a crossword puzzle.) I promise you, if I can handle eating a balloon filled with helium all by myself at one of the fanciest restaurants in America, you can go out to dinner alone too.

how to travel alone new york city
2) spend a day alone in your hometown

Congratulations! You’ve successfully dined out alone. The next step when learning how to enjoy Lone Traveller Holidays is to spend a day out in your hometown. My hometown is New York City, so I’m lucky because there’s a billion tourist attractions here. I generally like to spend my Tourist in My Hometown days partially wandering around and exploring and partially in one of our world class museums. Here you can see me cuddling up to Teddy Roosevelt in the Museum of Natural History. (He is immune to my charms.)

If you don’t live in a place that a tourist might like to visit, you can have this practice solo travel day in the nearest city. Or you can explore the surrounding countryside by car! Make your own little mini one day road trip. I truly believe just about any destination can be a wonderful travel experience, if you’re willing to see it with the eyes of love.

how to travel alone washington dc
3) travel somewhere close to home

OK, Internet Strangers, now you’re ready for the next Lone Traveller Holidays step! Take a weekend trip in another city. I recommend picking a place you can get to by car or train. You might not be ready to fly alone just yet. But do spend at least two nights in a hotel by yourself away from your family and loved ones. I promise they’ll still be there when you get back!

If you have trouble thinking of a destination, start with your hobbies. Do you love nature? Art and culture? History? Sports? Collecting Magic: The Gathering cards.? Where can you indulge in your passions while practicing solo travel?

I’m a museum junkie, so my first solo trip was to Washington DC, which is just a quick Amtrak ride away from New York City. Washington DC is the perfect place for museum lovers because so many of them are free. And as you can see from my photo, we can get up to some wacky hijinks in a DC museum, let me tell you.

how to travel alone japan
4) go for that real solo trip!

I strongly recommend enjoying your first Lone Traveller Holidays in a place you are dying to visit. My first long solo trip was to Japan. This might seem like a high level of difficulty, but I had been a Japanophile from a young age. I even studied Japanese in college. So I was convinced I’d be incomplete until I went to the country for myself. I consider Japan to be the perfect place to learn how to travel alone. The country is so safe, and the people are incredibly friendly, even if you go up to random statues and start tickling their toes.

But that’s my passion. What’s yours? Are you a foodie who’s dying to spend a week in Rome and eat all their gorgeous handmade pasta? Are you a nature buff who’s always wanted to hike the Grand Canyon? Are you a cricket fanatic who has always dreamed of watching the Boxing Day test match at Melbourne Cricket Grounds? No one will judge you here, I promise! Go out and live your dreams!

how to travel alone new orleans
5) smile!

Now that you have some steps for working up to a big solo trip, you’ll probably want some advice about how to keep your spirits up once you set out on the open road alone. My first piece of advice is a bit dorky, but I promise it works. Many studies have shown that smiling makes you feel more relaxed and happy. Smile even if you feel weird. Or you feel scared because you’re walking alone in a cemetery.

vancouver morgue

Or because you’re in a morgue in Vancouver…

how to travel alone

Or because you’re being stalked by a giant pig man in the Arizona desert.

how to travel alone dubrovnik

If a cheerful smile isn’t your bag, try an evil smile. Think of how all will bow before you when you sit on the Iron Throne. You’ll feel better and more confident in no time!

positive self talk
6) give yourself pep talks!

You can do this whether or not you are standing next to an Olympic torch. Positive affirmations aren’t for everyone, and I admit I find them rather cheesy from time to time. But telling yourself that people are judging you for being alone isn’t any less cheesy. I promise no healthy person is judging you. Tell yourself people are thinking you are brave and fabulous for traveling alone and they will be.

how to travel alone

One time a group of strangers asked if I was traveling alone because I was the Princess of Montenegro. (That’s a true story.) I’m not the Princess of Montenegro, nor am I the Princess of any other country in the Balkans. But this just goes to show that people are more likely to make up ridiculously cool stories about you than they are to think you’re a sad loner.

maaemo how to travel alone
7) prepare something to tell people

One of the best things about traveling alone is the chance to meet many kinds of wonderful people. I’ve had splendid conversations with everyone from the staff at Maaemo, the best restaurant in Norway

old moldovans

To these incredibly old Moldovans who once competed on Eurovision. It is likely that at some point these people will ask you why you are traveling alone. (Well, not those Moldovans because they didn’t seem to really speak English.) I always tell people the truth, that I started traveling as a coping mechanism after my mother died, but then I fell in love with the open road.

I don’t recommend outright lying, but prepare a stock phrase or two to tell people about why you are flying solo. Tell people that you wanted a change, or you were looking for adventure, or you feel the need, the need for speed.

how to travel alone

If you open up just a little, people will respond positively. Unless they are hateful goblins. Ignore those people.

how to travel alone
8) don’t be afraid to look ridiculous

This is maybe my top secret for how to travel alone. My whole life my biggest fear was making a mistake. A lot of people live their lives that way, and it’s no way to really live. Once I started traveling, I couldn’t stop making mistakes, and I realized the world wasn’t going to end if I mispronounced a word in Romanian or if I accidentally stole some shoes from a Japanese restaurant. Now I actively take pleasure in looking silly.

how to travel alone

I wear silly hats.

how to travel alone new orleans

I wear extravagant necklaces.

how to travel alone atlanta

I pretend I am in invisible prisons in Atlanta.

how to travel alone united kingdom

I pretend to be in actual medieval prisons in York.

how to travel alone new zealand

Sometimes I even pretend I am a hobbit.

If you laugh at yourself first, it won’t matter if other people are laughing at you. But probably they aren’t laughing at you. Probably they’re worried you’re planning to laugh at them, you brave solo traveler, you!

how to travel alone

That’s How to Enjoy Lone Traveller Holidays!

Do you feel you know how to enjoy Lone Traveller Holidays? Where’s the first place you want to go? And what’s the silliest hat you will wear once you get there? Please leave your comments below!

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