Let me take you back for a moment.

Do you remember when you first learned to ride a bike? Maybe you had training wheels.

Maybe a steady hand on your back from someone you trusted. And eventually, the moment came—you were off on your own.

A little wobbly. A little wide-eyed. But free.

That’s what your first solo trip can feel like. A little uncertain. Exhilarating. And absolutely yours.

If you’re anything like the amazing women I speak to daily smart, accomplished, and so ready for something just for yourself, you’ve likely been facing the reality of traveling solo. And… find yourself hesitating.

Where do I start? What if I get lonely? What if I get it wrong?

I’ve learned, both from experience and from supporting women just like you: your first solo trip should be one thing above all—DOABLE. 

This isn’t about proving anything to anyone or ticking off an epic bucket list. This is about you dipping a toe into your own freedom. In your own way. On your own terms.

🏡 Start Small, Stay Close

Think of your first solo trip as a gentle practice run. One of my favorite recommendations? Plan a simple overnight or weekend getaway somewhere close to home.

Not Paris. Not Bali. Not even a full week away.

Just one night.

Pick a place an hour or two away—a charming inn, a seaside village, a little boutique hotel downtown.

Somewhere you’ve maybe driven through before and thought, I should come back here one day.

Now’s the day.

Choose a town, a coastal spot, or even a boutique hotel in a part of your own city you’ve never explored. 

Here’s why this works: you already know the language, how to get there, and what to expect and…

Travel logistics are minimal—no airports, customs, or time zones to navigate solo.

 If you forget something, it’s not a big deal. 

You’ll feel independent without feeling overwhelmed. You’ll get a taste of solo travel—checking in on your own, ordering a meal alone, wandering without anyone else's agenda.

This kind of short, familiar trip gives you a soft landing into solo travel. It’s a confidence-builder, not a stress-test.

🏖️ Revisit Somewhere You've Loved

Another gentle first step? Return to a place you’ve already been—but this time, go solo.

That charming inn in the mountains you once visited with a friend? Or that beach town you used to vacation in with your partner? Go back.

Familiarity is powerful. 

You already know how to get around, what to expect, and where to find the best latte or sunset view.

You’ll be amazed at how different a familiar place can feel when it’s just you. 

You’re not adjusting to anyone else’s schedule or preferences. You get to see everything through your own eyes—and at your own pace.

Revisiting a place you already know—where the streets are familiar, the cafés still feel cozy, and you sort of know how things work—removes a layer of stress you didn’t even realize you were carrying.

You don’t have to learn it all from scratch. You just get to experience it through your own eyes this time.

That’s powerful.

🇬🇧Choose A Language Match

If you’re ready to venture further afield start with a destination where your language is spoken.

Whether it’s the UK, Ireland, Australia, or an English-speaking region of a country you’ve long dreamed of visiting…

Landing in a place where you can read signs, ask questions easily, and understand announcements brings a huge sense of relief...

Especially when you’re navigating jet lag and new surroundings on your own.

There’s something deeply comforting about hearing familiar voices around you after stepping off a long flight solo…

Or

Tuning in and out of other peoples conversations (lets be real, we all do it) and even that little bit of eavesdropping makes you feel less alone.

You’re exploring, but with a safety net.

✈️ When You're Ready To Stretch

Maybe you’ve taken a short trip, revisited a favorite place, or dipped your toes in with a long weekend.

And maybe now… you’re curious. What else is out there for a woman traveling solo?

🛳️ To Cruise Or Not To Cruise...

I keep toying with the idea of a cruise.

But here's the truth—the idea of being on a floating city just isn’t me. 

That said—it might be exactly right for you. And that’s what I love about solo travel: it’s a personal choice. It gets to reflect you.

What I am drawn to is the idea of a river cruise. Fewer people. Slower pace. Scenery that rolls past as you sip wine on the deck. That feels more like me.

Think fewer people, a slower pace, and scenery that glides past your window like a travel postcard come to life. You dock right in the heart of small towns and charming cities—no hours-long transfers or chaos. 

And there's often a natural blend of solo travelers and couples, which makes it easy to connect (if you want to), or just enjoy your own space.

It offers the comfort and structure of a cruise, but in a far more relaxed, elegant way.

If you’re considering your first solo trip and want ease, safety, and a touch of luxury without feeling overwhelmed, a river cruise might be the perfect middle ground.

🚞 I Love Trains (And You Might, Too)

I love trains. Always have. Always will.

There’s something timeless and romantic about settling into a window seat, hearing the low hum of the engine, and watching the world gently roll by.

It’s unhurried, calming, and quite frankly magical in my view. 

Now, most train trips are shorter—a few hours to get from one town to another, maybe a scenic route between two cities. 

Unless, of course, you’re chasing a dream trip like mine: the Orient Express. (One day... the Venice Simplon-Orient-Express is calling!)

Or the Rocky Mountaineer right here where I live in Canada. 

But even without the vintage luxury and white-gloved service, train travel is one of the best ways to stretch your solo travel wings.

You're alone, but never lonely.

There are people around you—locals, fellow travelers, the occasional chatty seatmate—but it’s not the same as being surrounded by swarms of tourists. 

You get to have the privacy of your own seat, your own little bubble of space, but if you choose you can connect in with passengers around you.

What I love most is that train journeys let you see so much without having to "do" so much. 

You’re moving, you’re traveling a real distance, but you’re not navigating airports or highways. There’s no checking in hours ahead or dealing with security lines. 

You just board, sit back, and let the landscape do the talking.

And if you're traveling solo for the first time, it’s a great bridge between independence and support. 

You can read, journal, sip tea (coffee for me), listen to music—or just watch the countryside shift from village to valley, mountain to coastline. 

You’re on your own, yes, but have the comfort of being in the presence of others.

🧘‍♀️ A Wellness Retreat Designed Just For You

Now this has to be my favourite “go to” for any trip but really ideal for your first solo trip.

When women ask me what kind of solo trip feels the most supportive, nurturing, and confidence-building— my immediate answer is a wellness retreat.

Why? Because quite frankly, they’re designed with solo female travelers in mind.

You won’t be the only woman arriving on her own—in fact, you’ll likely be surrounded by others doing exactly the same. 

It’s one of the few travel experiences where showing up solo isn’t just accepted, it’s expected. 

There's no awkwardness. No explaining.

Wellness retreats are geared to what women—especially women in midlife and beyond—often crave from travel:

• Time to rest and reset
  
  

• Healthy, nourishing meals
  
  

• Movement that feels good (not punishing)
  
  

• Gentle structure without pressure
  
  

• And moments of stillness to reconnect with yourself

I also love the flexibility that you can be as scheduled or not into activities and treatments.

You get to decide. No tour group timetables. No need to compromise. Just space to breathe.

What I love most is this: there’s no pressure to be social—but the opportunity is always there.

Meals are often served communally, or you can choose a quiet table. Conversations tend to be deeper, more reflective. 

You’re around women who are also seeking clarity, healing, or just a break from doing everything for everyone else.

Ssssh 🤫 Don't tell anyone but this is my all time favourite wellness retreat..

https://www.raewyncrist.com/blog/b/women-travel-over-50-Wellness-Retreat-Kamalaya

👩🏻 🧕🙍‍♀️Travel Solo In A Women-Only Group Tour

If you're the kind of person who’d feel more comfortable sharing your first solo adventure with other solo women travelers, then a women-only group tour might be a great way to embark on your solo travels.

This type of travel is growing fast. 

More and more women—especially those over 50—are choosing to travel solo, but not necessarily alone. 

They want the freedom of doing something just for themselves, but with the ease, safety, and connection that comes from being in a like-minded group.

You get to be with women who are likely in a similar stage of life—independent, curious, and ready for a new chapter. 

The beauty of these tours is that you get the best of both worlds:

• The logistics are handled for you
  
  

• You don’t have to eat alone (unless you want to)
  
  

• There’s built-in connection, without forced togetherness
  
  

• And you get to experience new places with women who understand why this trip matters

🧐 Forget The "Shoulds"

This one’s big. Maybe the biggest.

Your first solo trip doesn’t have to look like anyone else’s. 

You don’t need to backpack across Europe or cram in five cities in seven days. You don’t need to pose at iconic landmarks or follow someone else’s perfectly curated Instagram route.

You get to choose the why, the where, and the how. Want to wander around a museum and take breaks at every single café along the way? Do it. Prefer to sleep in and read a book by the pool? That’s just as valid.

This isn’t about proving you can be adventurous or brave or independent. You already are.

This is about discovering how good it feels to travel with yourself…

To say yes to what works for you! 

To know that you did this—just for you.

💭 One Last Thought

You don’t have to wait until you feel “ready.” That moment when everything lines up perfectly may never come.

Instead, start where you are.

Pick a place that feels comfortable, not challenging.
✔️ Keep it simple.
✔️ Keep it kind.
✔️ And keep it yours.

The training wheels are there if you want them. But you might just surprise yourself with how steady you already are.

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So cheers to wheels up to winging your way on your next travel building lasting memories.