When Life Pushes You Out of Your Comfort Zone: How I Discovered My Solo Travel Confidence

A woman walking down a narrow street

 I used to be that person who stared in awe, and let's be honest, a little envy, at my coworker who would casually mention her solo Disney trips.“You go to Disney… alone?” I’d ask, unable to hide my amazement. She’d just smile and say, “It’s the best way to travel.”

I thought she was crazy. Turns out, she was brilliant.

Then there was another colleague, a teacher who, at the end of every school year, would announce her plans to backpack through Europe. Solo. I was simultaneously impressed, envious, and absolutely terrified. The woman had nerves of steel, or so I thought.

Me? I’d traveled alone for work and school, but a vacation by myself sounded downright scary.

When Life Pushes You Out of Your Comfort Zone

Life has a funny way of making decisions for you. When my usual travel partners couldn’t make our planned trip, I had a choice: cancel altogether or take that brave step into solo travel territory.

Maybe it was a midlife shift talking, but I decided to go for it.

My first solo vacation? Disney World.

I know, I know, not exactly exotic. But there was comfort in choosing somewhere familiar for my first solo experience. Walking through those gates alone felt both terrifying and exhilarating.

And you know what? My coworker was right. It was the best way to travel.

I could ride what I wanted, eat when I was hungry, and pause to watch the fireworks without worrying about anyone else’s schedule.

That trip changed everything. It gave me the solo travel confidence I didn't know I had.

Finding My Solo Travel Sweet Spot

Emboldened by my Disney success, I made my next leap: Lisbon with a group of digital nomads. This wasn’t an escorted tour; we were a community of travelers who shared space and experiences but were free to explore at our own pace. It was the perfect balance of independence and connection.

Then came Spain. This time, I chose an escorted group tour. Some might say that’s not “real” solo travel, but I disagree. I traveled alone, yet had the reassurance of expert guidance and a built-in community.

It was solo travel with training wheels, and exactly what I needed.

Three Ways to Build Solo Travel Confidence

Here’s what I’ve learned through trial and (thankfully minimal) error: Building solo travel confidence isn't just one thing. There’s a spectrum, and the key is finding what works for you right now.

1. Pure Solo Travel

This is the deep end of the pool. You plan everything, navigate everything, and experience it all on your own terms. It’s empowering but requires preparation and confidence. My Disney trip taught me I was capable of more than I realized.

2. Solo Travel with Community

Think small-group experiences or digital nomad programs. You travel alone, but you’re not lonely. You have built-in companions and complete freedom to come and go. Lisbon showed me that solo doesn’t have to mean isolated.

3. Solo Travel with Support (Escorted Groups)

This is the best of both worlds, the independence of solo travel with the comfort of expert guides. You can push your boundaries while knowing support is there when you need it. Spain proved that solo can still include community and confidence.

Essential Tips for First-Time Solo Travelers

If the idea of solo travel feels overwhelming, start small. Confidence grows one step at a time.

Start with What Feels Manageable

Try solo activities at home first. See a movie, visit a museum, or enjoy a coffee shop on your own. These small steps help you feel comfortable being by yourself.

Choose a Familiar Destination

Your first solo trip doesn’t have to be far away. Pick somewhere that feels safe and known, like I did with Disney, or choose a nearby city you already love.

Research Is Your Best Friend

Learn about local customs, culture, and safety tips before you go. Being informed helps reduce anxiety and lets you focus on enjoying the moment.

Stay Connected, but Not Tethered

Share your itinerary with someone you trust and check in regularly, but resist the urge to spend the whole trip on your phone. Be present and experience your surroundings.

Trust Your Instincts

If something doesn’t feel right, remove yourself from the situation. Your intuition is one of your most valuable travel tools.

Pack Smart and Light

Dragging an overstuffed suitcase through Lisbon’s cobblestone streets taught me this lesson well. Less really is more.

The Magic of Choosing Your Adventure Style

Whether you’re eyeing that coworker’s solo adventures with curiosity or hovering between “maybe someday” and “never,” know this: There’s a solo travel style that’s right for you.

Maybe you’re ready for full independence, like my Disney trip. Maybe you’d thrive in a travel community like Lisbon. Or perhaps you’d love the comfort of an escorted tour like Spain, where freedom meets support.

Solo travel isn’t about proving yourself. It’s about discovering what kind of traveler you are and what brings you joy.

Finding Confidence Through Experience

As a travel advisor, I help new and returning travelers uncover their ideal travel style so they can explore confidently, comfortably, and on their own terms.

The right destination, pace, and level of support can transform fear into excitement and hesitation into empowerment.

If you’ve ever wondered whether solo travel could be for you, let’s explore it together. Whether you’re dreaming of a guided tour, a small-group cruise, or your first fully independent adventure, I can help you choose the experience that fits you best.

Your Solo Adventure Awaits

Your journey doesn’t have to start with a passport stamp. It can begin with curiosity.

Ready to find your solo travel style? Schedule a complimentary discovery chat or join my newsletter for solo travel inspiration, destination ideas, and practical advice for travelers who want to explore on their own terms.

Because everyone deserves that moment of walking through a new place and realizing, you’ve got this.