5 Things I Wish I Knew Before My First Solo Trip

There is something nobody tells you about planning your first solo trip.

It is not the packing list that trips you up. It is not the logistics, the flights, or even the language barrier if you happen to be heading somewhere new and unfamiliar.

It is everything that happens in your own mind before you ever leave home.

I have talked with so many women who are standing right at the edge of their first solo adventure, curious, a little nervous, and completely convinced that everyone else somehow figured this out more easily than they did. Especially those of us who spent years putting everyone else first and are only now giving ourselves permission to want something just for us.

They did not. We are all just figuring it out as we go.

If you are considering your first solo trip, or your first in a very long time, here are five things I truly wish someone had told me before I started.

1. Making the Decision Is Always the Hardest Part

If you are waiting to feel completely ready, I want to gently tell you something: that feeling may never fully arrive.

The decision to travel solo is where most women get stuck. Not in the planning. Not in the doing. In the deciding.

I know this firsthand. I have a tendency to over-research anything I want to do. I always want the perfect plan, whether it is travel or any new experience. But a few years ago, when my son’s college baseball team made a tournament in another state, I did not have time to get in my head. I had the dates, a flight to book, and a hotel to find near the field. I was nervous and excited all at once, and the urge to see those games gave me the incentive I needed. I booked the trip and went.

We second-guess ourselves. We feel guilty for wanting something just for us. We tell ourselves we will go next year, when the timing is better, when we have done more research, when we feel more confident. And somehow next year keeps becoming next year.

Fear and indecision have a way of disguising themselves as practicality. We convince ourselves we are being responsible when we are really just protecting ourselves from the discomfort of doing something new.

Here is what I have learned: the decision does not get easier with more research. At some point, you simply have to choose yourself. You have to decide that your desire to experience something meaningful is worth the discomfort of stepping into the unknown.

Everything else, the planning, the packing, the logistics, is manageable. The decision is the hardest part. And once you make it, something shifts.

2. There Are So Many People Ready to Help You

One of the biggest surprises of solo travel is discovering just how willing people are to help a woman traveling on her own.

We tend to imagine ourselves alone in every sense of the word, navigating confusing airports, eating by ourselves in restaurants, wandering unfamiliar streets without anyone to ask for help. And yes, there are moments of solitude. But loneliness is rarely the experience most women describe after their first solo trip.

What they describe instead is connection.

I experienced this in a very real way while walking the Camino in Spain. I was traveling with a girlfriend, so not entirely solo, but the lesson was the same. We had planned our hotels, our flights, and our route carefully. But we hit an unexpected snag when we discovered we had booked the wrong train and could not decipher the website or the language well enough to fix it. A fellow passenger overheard our dilemma and simply offered to help us navigate the changes we needed to make. Just a kind person who saw two women on their own and wanted to help. I will never forget that.

Fellow travelers who strike up conversations at the gate. Hotel staff who go out of their way to make recommendations. Shop owners who notice you are new in town and take five minutes to point you in the right direction. Online communities full of women who have been exactly where you are and are more than happy to share what they know.

Travel blogs, social media groups, websites dedicated entirely to women traveling alone, the resources available to you today are extraordinary. You are not navigating this without support. You just have to be open to receiving it.

I have found that people are receptive to a warm smile and a genuine request for help. Human nature is that we want to help others, that we feel good doing it. So do not be afraid to reach out. You may be surprised at the generosity of the human spirit.

3. Start Small and Just Slightly Outside Your Comfort Zone

There is no rule that says your first solo trip has to be a grand adventure across the world.

In fact, I would encourage you to begin much smaller than you think you need to. Not because you are not capable of something bigger, but because starting small gives your nervous system a chance to catch up with your courage.

That baseball tournament trip I mentioned earlier was exactly that for me. It combined the familiar, my son’s baseball, with the unfamiliar of a new state, a new hotel, and driving roads I had never seen. It was not overwhelming because I had an anchor. And one of my very favorite travel memories came out of that trip: stopping at a drive-through safari on the way, with animals wandering right up to the car. Several years later, the video still makes me smile when I need a boost. That trip was the push I needed to discover that I could travel solo.

Big changes all at once can feel overwhelming. Too many unknowns at the same time can turn excitement into anxiety before you even leave your driveway. But when you ease yourself in gradually, keeping some parts of the experience familiar while gently stretching yourself in others, you give yourself the chance to actually enjoy it.

Maybe that looks like visiting a city you have been to before, but staying somewhere new and exploring on your own schedule for the first time. Maybe it is a weekend trip an hour from home before you book something farther away. Maybe it is one night alone at a quiet bed and breakfast just to see how it feels.

There is no version of this that is too small to count.

Every single solo experience, no matter how brief or how close to home, builds the confidence you need for the next one. Trust the process. Let yourself grow into it.

4. Plan and Prepare, Then Give Yourself Permission to Change

Preparation matters. I am a firm believer in doing the work ahead of time so that the actual experience can feel as relaxed and enjoyable as possible.

Research your destination. Know your accommodation. Understand the basics of getting around. Share your itinerary with someone you trust. Have your documents organized and your emergency contacts saved. The more you can take care of before you leave, the less mental energy you will spend managing logistics while you are trying to be present.

I learned this the hard way on a trip to the East Coast. I had planned the trip carefully, scheduled experiences I was genuinely excited about, and left room for exploration. What I had not done was save everything in one place. Standing in line for an experience I had been looking forward to, I realized I had never downloaded my ticket. I held up the entire line while I searched frantically through my emails trying to find the confirmation link, face flushed, muttering apologies to the people behind me. A few extra minutes before I left home to collect everything into one folder or app on my phone would have saved me that particular moment of entirely avoidable anxiety. Prepare well. Then trust that preparation and go.

But here is the other side of that truth: over-planning can become its own form of avoidance. When we spend months preparing for every possible scenario, we are sometimes really just delaying the trip itself.

Plan enough to feel genuinely prepared. Then go.

And once you are there, give yourself full permission to change the plan. The restaurant you had your heart set on might be closed. The museum might not move you the way you expected. You might wake up on day two and feel like doing absolutely nothing, and that might turn out to be exactly what your soul needed.

Travel teaches us things about ourselves that we cannot learn in advance. Some of the most meaningful moments happen in the gaps between the plans, in the detours, the unexpected conversations, the quiet afternoons that were not on any itinerary.

Make the plan. Then hold it loosely. And when things do not go perfectly, learn from them and keep going. Every mistake is just information for next time.

5. Only You Know What Is Right for You

This one may be the most important of all.

When you begin talking about traveling solo, especially if it is something new for you, you will quickly discover that everyone has an opinion. People who love you will worry. People who do not understand will question your judgment. Even well-meaning friends and family members can plant seeds of doubt without realizing they are doing it.

I felt this when my husband and I were considering relocating in retirement and I decided to drive through Idaho on my own for three days to explore different areas. Loving family members tried to convince me that a woman driving alone through another state was not safe. At first I hesitated. And then my stubborn pride kicked in. Of course I could do this. Rent a good car, stay in well-known hotels, travel during the day, take safety seriously. That is exactly what I did. And it was one of the most freeing experiences I have had.

It is easy to let those voices become louder than your own.

Human nature makes us susceptible to the opinions of the people we care about. We want their approval. We do not want them to worry. We sometimes shrink our own desires to make others more comfortable. And before long, we are second-guessing a decision that felt completely right before we mentioned it to anyone.

Here is what I want you to remember: you are the only person who fully knows your own needs, your own desires, your own level of readiness, and your own reasons for wanting this experience.

Not your sister. Not your best friend. Not your adult children or your colleague who has never traveled alone and cannot imagine why you would want to.

You.

Allow yourself the dignity of making your own decisions. Allow yourself the pleasure of finding out what works for you through your own experience rather than someone else’s fears. You may make choices that turn out differently than you expected. That is part of it. But they will be your choices, and they will teach you something that borrowed opinions never could.

The women who travel most meaningfully are not the ones who had everyone’s approval before they left. They are the ones who trusted themselves enough to go anyway.

You Do Not Have to Have It All Figured Out First

If there is one thread connecting all five of these lessons, it is this: you are more capable than you are giving yourself credit for.

The fear is real. The hesitation makes sense. But so does the pull you feel toward something more, something deeper, more intentional, more fully yours.

You do not need to be fearless. You do not need to have the perfect itinerary or the right travel companion or the complete blessing of everyone around you.

You just need to decide that you are worth the trip.

And then go.

Before you take that first step, grab the free Travel Readiness Checklist below. Everything you need to feel genuinely prepared — including a faith and mindfulness reminder to leave space for joy.