How to Travel Alone: 9 Exercises to Prepare You for Your First Solo Trip

Has solo traveling ever crossed your mind, but you weren’t sureĀ how to travel alone? Exercising your freedom to go wherever and whenever can be a great experience. However, preparing for your FIRST-EVER solo trip might be a daunting task. Maybe you aren’t used to spending a lot of time alone, so you’re not sure how to feel about the idea of an entire solo vacation.

If you are curious about how to start solo traveling, here is a weekly exercise guide that will help prepare you. Each of these nine steps was designed to help you feel more comfortable on your first solo trip. By jump-starting your experience exploring alone before you leave home, you will soon be prepared to solo travel anywhere.

How to Travel Alone: 6 Starter Exercises

Exercise 1 – Eat Alone

Single place setting on a wooden table - how to travel alone


The goal of this exercise is to help you feel comfortable eating alone in different environments by starting with familiar ones. Instead of doing take out on your first solo trip, you can have the full local cuisine experience.

The biggest hurdle for me at the beginning of my first solo trip was eating alone. I felt very self- conscious and thought people were looking at me, thinking I was a lonely person. But the reality was that people were very much involved in their own conversations. Why bother to care what they think? Eating alone is an uncomfortable exercise to start with, especially when you do it without a phone or a book, but it’s a crucial step in learning how to solo travel. I recommend trying it first at your favorite restaurant, then moving to different kinds of restaurants: more crowded, less crowded, high end, food trucks, etc.

Exercise 2 – Try a Different Coffee Shop

Xin smiling with coffee mug while solo traveling

The goal of this exercise is to help you start exploring your surroundings alone in baby steps.

Trying a different coffee shop can take you through a different route of your city. Even if you only drink Starbucks, there are Starbucks everywhere; visiting a new location can introduce you to a whole new neighborhood. Find some new favorite spots and start a coffee shop rotation as you continue to explore a mostly familiar place.

Exercise 3 – Take a Solo Shopping Trip

The goal of this exercise is to prepare you to make independent purchases/budget decisions while solo traveling.

A solo shopping trip is a great time for you to practice making your own spending decisions. You have to answer the questions “Should I buy this or not?” and “Will there be luggage room for this or will I have pay extra for checked bags?” without anyone there to advise you. When you are solo traveling, you have to make every single decision that will impact the budget, expense, and luggage space of your trip. Practice making wise money choices on a normal shopping trip and you’ll be more prepared for how to travel alone.

Exercise 4 – Explore Your Own City

Woman with city map on a solo trip

The goal of this exercise is to help you experience the freedom of solo traveling in a familiar environment.

Consider the law of romance: learn to love yourself first so you can love others. This applies to solo travel destinations as well: learn to love your city first, and then you can love other cities. Try going on a city tour or just exploring the city by yourself to learn about what makes your everyday environment unique. This experience can help get to know your solo exploration style. As a bonus, the next time your friends and family come to town, you will have more things to show them!

Exercise 5 – Walk around at Different Hours

The goal of this exercise is to help you develop your walking style, which can be especially important if you are wondering how to travel alone as a woman safely.

I developed a night walking style after my first solo trip to Missoula, Montana. The area I stayed in was not the cutest, and I ended up walking around at 10:00 pm. My night walking style is to walk fast and stare straight with my resting bitch face and all the confidence I can squeeze out of myself. Try this exercise and find what style you want to develop for different environments and times of day.

Exercise 6 – Trick Your Mind

Woman sitting alone on a train looking out the window

The goal of this exercise is to help you fake it until you make it.

Whenever you are in a different city, don’t think of it as, “Oh, I am in a strange place.” Think of it as, “Oh, this is just a different part of my own city.” It’s all about tricking your mind into feeling comfortable in a new environment! (So what if you look like a yeti at night, who cares? You get to fully embrace and accept your weirdo sides.)

How to Solo Travel: Three Follow-Up Exercises

Now that you have mastered the first six exercises for how to travel alone, you are ready to take on your first solo trip! Still, you may want to ease your way into it by starting small and working up to a longer vacation. Here are three follow-up exercises for your first few solo trips to turn you into a pro solo traveler!

Exercise 7 – Go on a Solo Hike

Going on a solo hike can be a great activity for you to build up your confidence as you begin to travel alone. For your first solo hiking trip, I do recommend choosing a hike you have done before. This way, you are familiar with the environment just in case anything happens. On this hike you have the opportunity to get prepared and familiarized with all the safety equipment you need for a longer solo trip.

Exercise 8 – Reflection Time

Woman alone with tree in the foreground

After your first solo weekend trip, take some time to reflect on how you felt. What did you like and dislike? How do you want to prepare differently for your next solo trip? Did you feel uncomfortable at any stage of the process? If so, you can plan to either take more time or stop and rest up on your next adventure. Solo traveling is a process that can be customized to your need, so feel free to adjust based on how you felt the first time around.

Exercise 9 – Turn Weekend to Week-long

Continue doing solo weekend trips until you feel comfortable doing a week-long trip. On these longer trips, you get to experience staying in a hotel/Airbnb, taking a plane, or driving alone for longer distances. As you learn to love week-long solo trips, they will soon turn into 2-week, month-long, 2-month, half-year-long trips, etc…

I see solo traveling as a very rewarding experience. During these trips, you are the sole decision maker and have to be flexible with your schedule. I hope this exercise guide on how to travel alone can help you to feel more prepared on your first solo trip, and all the ones that will follow.

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