The Heart of the Journey Is the Circle Around You

Michelle Laudermilk
Jul 29
3 min read

✨ Exploring the power of community, connection, and shared experience for women who travel with intention.

A circle of women travelers laughing and connecting during a small group tour. — You don’t have to go far to go deep — women’s small group travel brings unforgettable moments and genuine connection.

At this stage in life, many of us are craving something different from travel — not just more places, but more meaning. Not more miles, but more connection.

That’s why I created Infinite Vagabonds: to design travel experiences for women 50+ who are seeking beauty, culture, and community — not just sightseeing. And at the heart of everything we do is the circle: small group journeys rooted in trust, intention, and shared experience.

🧭 Why Who You Journey With Matters

Travel doesn’t happen in isolation. It’s shaped by who’s beside you at the dinner table, who laughs with you on the van ride, who helps you see something in a new light. Whether you’re navigating a new city or pausing to journal in the quiet of the morning, having the right people around you can turn a trip into a turning point.

For women over 50, that kind of connection can be transformative. In small groups, we’re free to be ourselves — no pressure to impress or perform. Just space to breathe, reflect, and connect.

A solo traveler takes a quiet moment to journal and reflect. — Enjoying a peaceful moment in the garden, this traveler reflects on the importance of companionship, surrounded by nature's beauty.

👭 What It Means to Be in a Circle

A circle is more than a number — it’s a feeling.

It means:

– You’re not a stranger.

– Your voice matters.

– You’ll be seen and supported.

In our Founder’s Circle tours, we keep groups intentionally small (6–10 travelers), so conversations can be meaningful, relationships can grow, and every moment feels personal. The women who join our journeys tend to share common values: curiosity, kindness, open-mindedness, and a love of culture and story.

Older woman smiles, adjusting black helmet with goggles on a sunny road. She wears a denim jacket and polka-dot scarf. Greenery in background. — Embracing the joy of the ride, proving that age is just a feeling.

🌎 When Community Becomes the Destination

One of the most beautiful parts of small group travel is watching the group become the destination — a source of insight, humor, and support. From shared meals to group circles, from street musicians in New Orleans to quiet reflections in a Michigan vineyard, the magic isn’t just in the itinerary. It’s in the way we show up for each other.

This kind of travel invites us to slow down. To ask different questions. To let the journey shape us.

Two smiling women on a boat, one in a straw hat and colorful dress. They're embracing, with a scenic lake and mountain view behind. — Two women enjoying a sunny day by the water, embracing the joy and connection of community.

🌀 Why This Matters — Now More Than Ever

In a world moving faster by the day, many of us are longing for something more grounded. For travel that feeds our spirit, not just our photo album.

For women in this chapter of life — maybe post-career, post-parenting, or simply post-burnout — small group travel offers a return to self. But more than that, it offers the joy of shared discovery.

That’s the purpose behind the Founder’s Circle. These aren’t just trips — they’re the beginning of something much more enduring.