How Group Travel Helps Women Over 50 Build Confidence for Solo Travel

Curious about solo travel but not quite ready to go alone? Discover how group trips can help midlife women build confidence, connection, and courage.

How Group Trips Help Women Travel Braver with Doni Belau of Girl’s Guide to the World // 180



“Group travel can be the gentle first step that reminds you—you can do this on your own.”

How Group Travel Helps Women Over 50 Build Confidence for Solo Travel

Are you standing at the edge of something new…
feeling the pull toward solo travel, but not quite ready to take that step alone?

What if there was a gentle bridge between where you are now and where you want to go?

For many women, group travel becomes that bridge—a way to step into the world with support, while still reclaiming independence.

In this episode, Cheryl sits down with Doni Belau, founder of Girls’ Guide to the World, to explore how group travel can help women travel braver, especially in midlife.


Why So Many Women Feel Stuck Before Their First Solo Trip

For women over 50, the desire to travel often returns in a new way.

There’s more space.
More time.
A quiet sense of “What’s next?”

But alongside that desire often comes hesitation:

  • Is it safe?
  • Will I feel lonely?
  • What if I don’t know what I’m doing?

These questions are real—and they matter.

But they don’t have to stop you.


Group Travel as a First Step Into Solo Travel

Group travel offers something powerful:

You go on your own…
but you’re not alone.

As Doni shares, many women join group trips as a first step—a way to experience independence without the full weight of planning everything themselves.

It becomes a kind of “practice ground” for solo travel.

You begin to see:

  • You can navigate new places
  • You can enjoy your own company
  • You can make decisions for yourself

And slowly, confidence begins to build.


The Power of Connection on the Road

One of the most surprising gifts of group travel is connection.

Not forced or surface-level—but meaningful, life-giving connection.

Women gathering together, sharing stories, laughing over meals, and forming friendships that often extend far beyond the trip itself.

Because even as independent women, we still need:

  • Community
  • Shared experiences
  • A sense of belonging

And sometimes, it’s easier to find that in a room full of women walking a similar path.


Why Travel in Midlife Feels Different

Travel in your 20s is often about discovery.

But in midlife?

It becomes something deeper.

It’s about:

  • Remembering who you are
  • Reclaiming parts of yourself
  • Creating space to hear your own thoughts again

As Doni shares, stepping away—even briefly—can feel like a reset. A return to yourself.


Safety, Confidence, and Taking That First Step

Safety is one of the most common concerns for women considering solo travel.

And it’s a valid one.

Group travel can help ease that fear by providing:

  • Structured itineraries
  • Local guides
  • Built-in support
  • A shared sense of awareness

But over time, something shifts.

As Cheryl notes, the more you travel—even in small ways—the less fear takes center stage, and the more confidence grows.


Travel Changes You—In Ways You Might Not Expect

There’s something that happens when you step outside your everyday routine.

Your mind wakes up.
Your perspective widens.
Your identity begins to expand.

Even a short trip can interrupt old patterns and create space for something new.

And sometimes, that’s exactly what your next season needs.


You Don’t Have to Do It All at Once

If solo travel feels like too big of a leap right now, that’s okay.

You don’t have to jump straight into the deep end.

You can begin with:

  • A group trip
  • A short getaway
  • A simple step outside your comfort zone

Each step builds the next.

Each experience adds confidence.


A Gentle Invitation Forward

Maybe this isn’t just about travel.

Maybe it’s about becoming.

Becoming more confident.
More curious.
More connected—to yourself and the world around you.

And if group travel feels like the right first step, trust that.

You don’t have to have it all figured out.

You just have to begin.


If you’re wondering what your next step could look like, this is something Cheryl supports women with through 1:1 coaching—helping you discern what kind of travel fits your season, your story, and your readiness.

Learn more here:

https://cherylbeckesch.com/work-with-me

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hey sister travelers

i'm cheryl

Solo travel coach, podcast host, and Christian woman on a mission to help other midlife women find healing, freedom, and deeper faith through God-led adventures.

After years of raising a family and walking through heartbreak, I rediscovered my purpose on the road… and now I help others do the same. 

Cheryl Beck Esch, Solo Travel Coach, Faith-Based travel coach
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