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Tips to Make your First Solo Trip a Little Less Intimidating

Solo travel can be nerve-wracking. I won’t pretend that it’s not, especially if it’s your first time adventuring out on your own. But with preparation and a little courage, I firmly believe that everyone is capable of solo travel.

Thinking about trying it out? Here are a few tips to make your first solo trip a little less intimidating!

a solo traveler in front of a Monet painting at MOMA in New York City

#1 - For your first solo trip, visit someplace you’ve been before

I can already hear you protesting. “Isn’t the point of solo travel to charge bravely into the unknown?” you say, “To boldly go where no one has gone before?”


Sure, sometimes solo travel is like that. But for me, the whole Point(™) of traveling solo is to experience a place entirely on your own terms. Completely at your own pace, on your own schedule, and led by your own desires. There is absolutely no reason you can’t do this in a place you’ve already visited before.

My very first solo trip (all the way back in 2015!) was to Stratford Ontario, where I visited the Stratford Shakespeare Festival. I’d already been to the Festival twice before, both times with tour groups organized by my college. That meant I already had a good grasp of the layout of the town, how to get around, and where I’d be able to find the things I needed.

I loved the solo experience so much that it’s become my dominant method of travel. I never imagined myself as a solo traveler until necessity made me try it. ("Necessity" here meaning a desperate need to drive to Canada to see Hamlet and not having anyone with that same level of Shakespeare fanaticism in my life yet.) Try it. You just might surprise yourself.

#2 - Visit someplace with a culture similar to yours

a solo traveler in a kayak on Lake Superior at Pictured Rocks National Lakeshore

Friends, I am a huge fan of galivanting off to Paris with a loose itinerary and just enough French to be dangerous. I do not recommend doing this your first time out of the gate.

For your first solo trip, pick a destination that has a familiar feel about it. Ideally, again, one that you’ve visited before. If you’re from a city, pick one in a neighboring state and hop over for a visit. If you’re super comfortable in the outdoors, pick a state or national park and go hiking for a few days. If you’re from a small town and cities creep you out, get yourself to another small town. Is there maybe a childhood vacation spot you could revisit as an adult?

The point is, you don’t have to throw yourself off the deep end right away. Traveling solo is a whole separate skill set from group travel, and you’re allowed to be a beginner. You're allowed to make your first solo trip as easy for yourself as possible. Even if the destination doesn’t seem particularly glamorous, I promise you will have a great time. You have nothing to prove. The whole point of traveling alone is that this is YOUR vacation. In travel as in everything, you do you, babe.

#3 - Schedule a phone date (or two) with a friend

a solo traveler with a pink beverage at Pike Place Market in Seattle

Most newbie solo travelers are worried that they’ll eventually get lonely. While this fear is not completely unfounded, there are some really easy ways to help with this. You’ll have told a few people where you’re going, so ask those people if you can call them on your first night. Or your second night. Or every night after dinner. Having a person or two “on call” for you -people that you can text or call or just generally chat with while you’re away- can go a long way toward making you feel safe and comfortable.

I have several people that I Snapchat constantly while I travel to share all my cool experiences and vent about my mishaps. (Yes, I’m old. Feel free to roast me for my Snapchat use in the comments). Yes, you’re traveling solo, but that doesn’t mean you have to completely shut out the rest of your life. You can still stay connected virtually with your favorite humans. It doesn't make you any less of a solo traveler.

#4 - Take a test drive in your hometown before you go

Take yourself out to dinner, or to the movies, or visit a local museum all by yourself.

Practice saying “table for one” with confidence. Grab a ticket to a movie and have total control over your seat choice and don’t share your popcorn. Wander through a series of local galleries at your own pace. “Traveling” solo in your hometown is a great way to get your feet wet before you take the leap.

So take the leap my friend! There are a million ways to see the world, and you’ll never know which ones you like until you try. Give solo travel a try. It’ll amaze you.

Still on the fence? Click here to read my ultimate Solo Travel Mythbusting Guide!

Have questions about solo travel that you'd like to ask me directly? I've been traveling solo for eight years and I would love to answer your queries! Visit me Here to send me a message or subscribe to my email list.

Love and Shenanigans,


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