Sherry solo traveling standing next to a car
September 1, 2025

“Isn’t it scary to travel alone?”
“Don’t you get lonely?”
“Who takes your photos!?”

If I had a dollar for every time someone asked me one of those questions, I’d have a beachfront villa in Bermuda by now—with a full-time tea sommelier, thank you very much.

But here’s the truth:
Solo travel changed my life.
And no, I’m not lonely. I’m free.


Falling in Love with Solo Travel (Later in Life)

I didn’t start traveling solo in my twenties. My solo era arrived later, like a fabulous guest who shows up fashionably late but steals the show.

In my 50s, I found myself craving space. Not the “move away and start over” kind—but the type of space that lets you breathe, reflect, and reconnect with the version of yourself that got a little buried under expectations, busyness, and (let’s be honest) a few decades of people-pleasing.

So I booked the trip. I packed the camera. And I went.


The Magic of Your Own Rhythm

When you travel solo, something magical happens:
You wake up when you want.
You eat what you crave.
You stop to photograph flowers or linger at a street musician’s performance just because you feel like it.

It’s freedom in motion.
And in those moments, you realize—you’re never really alone. You’re surrounded by possibility, by connection, by you.


Real Talk: It’s Not Always Glamorous

There are moments where you’ll miss having someone to split dessert with. Or someone to double-check your directions when Google Maps is clearly drunk. But those moments? They pass.

And in their place, you gain something so much more powerful:
Confidence. Clarity. A deeper trust in yourself.

Plus, let’s not overlook the pure joy of not having to compromise on dinner plans. IYKYK.


For the Women 50+ Who Are Curious

If you’re reading this and thinking, “Could I really do that?”—the answer is YES.
You don’t have to backpack across Southeast Asia or hike a mountain in Peru to be a solo traveler. It can be a weekend in Quebec, a cruise in the Mediterranean, or a cozy tea-filled escape to Bermuda.

It’s not about where you go.
It’s about showing up for yourself in a brand new way.


So no, I’m not lonely.
I’m lit up, fully present and soaking in every unscripted, unforgettable moment.
And I want that for you, too.


✨ Ready to dip your toe into solo travel?
Let’s design your first (or next!) adventure together.
📩 Reach out here or find daily inspo on Instagram @sherryonshore.

Solo but Never Alone: Why I Love Traveling by Myself