Solo Travel vs. Group Travel: You Don't Have to Pick a Side

I love solo travel. And yet I started a group travel company.

I understand that sounds like a contradiction.
It's not, but I understand why it lands that way.

Solo travel is one of my favorite things in the world. The freedom to shape my day exactly how I want. No coordinating, no compromising, no waiting on anyone to decide where to eat. And my personal favorite part, the anonymity. No one knows you. You can walk through a city and just exist, fully inside your own experience, while life buzzes around you. As an introvert, that feeling is something I'll never stop chasing.

Solo travel gives you something that nothing else quite can.

But it's not the only kind of travel worth experiencing. And it took me a while to admit that.

What solo travel actually gives you

Solo travel is where you go to come back to yourself.

The freedom is real. So is the quiet. The ability to move at your own pace, follow your own curiosity, and sit with your own thoughts without someone else's energy in the room. There's also a quiet confidence that builds when you navigate a new place on your own. When you realize you can figure out the trains, navigate to a viewpoint you’ve been craving, and realize you're more capable than you give yourself credit for.

If what you're craving is independence, stillness, or clarity, solo travel is almost always the right answer.

What solo travel doesn't always give you

I'll be honest about the part that took me longer to admit.

Solo travel can be lonely. Not always, not dramatically, but sometimes you're in the middle of something genuinely beautiful, and you feel this small, unexpected ache. Wishing there was someone next to you. Not to talk, just to be there and share in the experience.

There are also the practical realities. Solo travel is expensive. You're not splitting anything. And you're also the only one doing the research, the planning, the logistics. Which can be great, but it can also be overwhelming.

Some experiences are just meant to be shared.

Some moments need another person in them

Hawaii is one of my favorite places on earth.

I've also learned it's not a solo destination for me.

I want to snorkel and be able to point things out to someone. I want to sit down afterward with a drink and talk about what we just saw. I want to on a long drive along the North Shore with the windows down and the music up. I want to watch the sunset over the water and not feel that small, quiet loneliness I sometimes felt when I was there alone.

Same with European Christmas markets. You can go alone. The lights are still beautiful. The mulled wine still hits. But laughing with someone over something ridiculous you found at a stall, or sharing your haul at the of the day in the hotel room, all cozy in your pj’s — that's a different kind of experience. One that needs another person to be complete.

There are trips meant for independence and quiet.

And there are trips that are better shared.

What group travel does well. When it's done right

Group travel has a reputation problem. People picture packed itineraries, 6am wake-ups, and a bus full of strangers in matching lanyards being herded from place to place.

That's not what I believe travel should feel like.

The trips I create through Say Yes are intentional. Slow mornings. Long dinners. Free time built in every day so you can wander off on your own, journal, get lost, find a coffee shop, and just sit.

It's not about filling every moment. It's about creating space for the right moments to happen.

And one of the things I've watched happen over and over again: the women who show up for these trips have no idea what they're walking into. There's always a little awkward energy at first. You might have to share a bathroom with someone you just met. You're all figuring out the rhythm together.

And then it shifts. Quickly.

Real conversations start happening. Not surface-level ones, actual conversations. People open up faster than you'd expect when they feel safe. You start laughing more than you thought you would. You find yourself weirdly grateful to be there, with these specific people, in this specific place.

"But what if I don't vibe with the group?"

This is the question I get most often. And honestly, I ask myself the same thing every time.

I don't want to be stuck somewhere with people whose energy doesn't match mine either. That's a real concern, and I take it seriously.

What I've noticed is this: the women who are drawn to Say Yes trips tend to already have something in common. They're curious. Open. They're not passive — they chose to be there. No one dragged them along.

I curate the experience and the energy with that in mind. And more often than not, the group dynamic falls into place in a way that feels pretty natural.

You don't have to choose

This is the part I care most about.

You don't have to decide if you're a solo traveler or a group traveler. You can be both, at different times, depending on what you need.

Some trips will call for independence and space. Take that solo trip. Shape every single day exactly how you want.

Other trips will call for connection, shared energy, and the kind of experiences that are better with others. For those, try a group trip. Let someone else handle the planning. Show up and be present.

Both are worth having. Both will give you something the other can't.

The question isn't which type of traveler you are. The question is: what do you need right now?

Insider's tip: You don't actually have to choose on a Say Yes trip. Every trip can be extended. Try a few days solo before the group arrives, or a few days on your own after everyone heads home. If you need time to get your sea legs, decompress, or just wander somewhere new on your own terms first, tack it on. The solo time and the group experience don't have to be separate trips.

Come take a look at what's coming up. Find the trip that feels like your next yes.