Solo Travel or Traveling with Friends? How Women Over 50 Can Choose What’s Right // 172
“Sometimes the best trip isn’t about where you go—but how honestly you honor what you need.”
Solo Travel vs Traveling with Friends After 50: How to Choose What’s Right for You
Have you ever started planning a trip…
and suddenly found yourself wondering:
Should I go alone? Or should I invite someone?
Maybe a friend offers to join.
Maybe plans shift unexpectedly.
Or maybe you’re simply unsure what you actually need right now.
If you’ve felt that tension—you’re not alone.
This is a decision many women face, especially in midlife, when travel begins to feel more intentional.
There’s No “Right” Way to Travel
Let’s begin here:
There is no one right way to travel.
Solo travel isn’t better.
Traveling with friends isn’t better.
What matters most is this:
What do you need in this season?
The Beauty of Solo Travel
Solo travel offers something unique and deeply personal.
It gives you:
- Freedom to choose your destination and pace
- Space to reflect and reconnect with yourself
- Flexibility without compromise
- Opportunities to meet new people more naturally
There’s a quiet confidence that grows when you navigate the world on your own.
And often, you discover parts of yourself that had been set aside for years.
The Gift of Traveling with Friends
At the same time, traveling with others brings its own kind of richness.
You get:
- Shared memories that last a lifetime
- Laughter and connection along the way
- Shared costs for accommodations and transportation
- A sense of familiarity and comfort
There’s something beautiful about experiencing a place together.
The Hidden Challenges of Traveling Together
But let’s be honest—traveling with others isn’t always easy.
It often requires:
- Compromise on activities and schedules
- Alignment in budget and travel style
- Patience with different personalities
- Flexibility when plans shift
Even close friendships can feel strained when you’re together 24/7.
And sometimes, you don’t discover that until you’re already on the trip.
Questions to Ask Before Traveling with a Friend
If you’re considering traveling with someone, it’s worth asking a few honest questions:
- Do we enjoy similar activities?
- Do we have similar travel styles (budget vs luxury)?
- Are we compatible in energy and temperament?
- Do we need similar amounts of alone time?
- What are each of our expectations for this trip?
These conversations can prevent unnecessary tension—and create a more peaceful experience for both of you.
The Importance of Being Honest About Your Intentions
This may be the most important part.
If your heart is calling you to travel solo…
it’s okay to say that.
Kindly. Gently. Honestly.
Because saying yes to something you don’t truly want can lead to:
- Resentment
- Disappointment
- A trip that doesn’t feel aligned
And that’s not what you want—for yourself or your relationships.
Let Your Purpose Guide Your Decision
Instead of asking:
“Should I travel solo or with someone?”
Try asking:
“What is the purpose of this trip?”
Because your purpose will guide your choice.
If you’re craving:
- Rest and reflection → Solo travel may be best
- Connection and shared joy → Travel with friends may fit
- A mix of both → Consider blending solo time with shared experiences
There’s room for flexibility.
There’s room for creativity.
You Can Do Both
It doesn’t have to be all or nothing.
You might:
- Arrive early and spend a few days solo
- Extend your trip after a group or friend experience
- Build in intentional alone time during a shared trip
Travel can be shaped to meet you where you are.
A Gentle Reflection
What are you truly needing right now?
Not what others expect.
Not what feels easiest.
Not what avoids discomfort.
But what you need.
Because honoring that…
is where the most meaningful travel begins.
If you’re unsure what kind of travel fits your current season, Cheryl supports women through 1:1 coaching—helping you discern your next step with clarity and confidence.
Learn more here:
