The First Girl Trips Adventure: How a Simple Idea Turned Into Real Connection

I should probably start by saying that this isn’t a polished founder success story. This is a “holy hell, I actually did it” story.

Two and a half years. That’s how long it took from the first spark of an idea to me finally hosting my first girls trip in Canada. Two and a half years of daydreaming, overthinking, stalling, second-guessing, doubting, re-planning, and occasionally crying in my car.

Then one day, I decided to stop spinning my wheels and actually just do the thing.

And let me tell you, it was perfect. So perfect, in fact, that after the high wore off, I absolutely crashed.

The Post-Trip Crash (Otherwise Known as My Brain Being a Jerk)

When the last guest left and as I was cleaning up the boats, it took less than five minutes before the doubts started to creep in. Instead of basking in the glow of a what had just happened, my brain immediately whispered:

What if that was a fluke?

Aaaaand, cue the spiral.

I questioned everything. Did my guests actually enjoy themselves, or were they just being polite Canadians? Was it the destination, the timing, the people… or was it Jeanette, my high-energy bestie I’d roped in to help me? Did I somehow just stumble into beginner’s luck?

Here’s what didn’t cross my mind in those early post-trip hours: the hundreds of hours I’d poured into building this business. The website design. The social media. The writing. The marketing. The first aid course. Getting my travel agent licence. Reaching out to Canadian businesses. Shopping for food. Making the food. Building the timeline. And on, and on.

Nope. None of those things could have possibly contributed to the success. Did I mention my brain is a jerk?

Thankfully, I pulled myself together, slept for what felt like three business quarters, and reflected. The answer became clear: it wasn’t a fluke. It worked because it was designed for connection.

Why I Created Girl Trips

Girl Trips was born from a simple truth: women need space to connect. Not just a vacation, but a chance to exhale, meet like-minded women, and share something real.

I’m building what I like to call a connection company cleverly disguised as a travel company.

The older we get, the harder it becomes to make new friends. It takes roughly 200 hours to build a deep friendship. I can’t give you all 200, but a weekend away? I can give you one hell of a head start.

For two and a half years, this idea lived rent-free in my head. I knew women needed this, but fear kept me stuck. What if no one signed up? What if they did, and it went terribly? What if my snacks weren’t good enough?

But here’s the thing: when you finally stop letting fear drive the bus, or boat in this instance, magic can actually happen.

What Made This Girls Trip in Canada So Special

The first Girl Trips getaway worked because of three simple things: the people, the setting, and the small touches.

This trip wasn’t just a group of strangers on a boat. It was a collection of incredible women from different backgrounds and age groups who showed up open, curious, and ready for something real. The youngest and the oldest bonded over shared stories. Introverts found their people. Laughter echoed across the water late into the night. (Okay, fine, until about 10 p.m. We’re over 50, don’t judge us. We party early, then sleep like champions.)

Connection happened naturally because the space was designed for it.

The Girl Trips Traveller

I’ve learned that there’s a distinct profile of a Girl Trips traveller, and this first group helped me define it. These women were open to new adventures, raw and real, easygoing but definitely not pushovers, and funny as hell. (It took me a minute to fully get Carol’s humour because her wit was even drier than mine, and that’s saying something.)

They were supportive in the most beautiful ways: arms around a woman still grieving the loss of her spouse, and a conspiratorial “what revenge would you like us to take?” offered to someone freshly wronged.

They were loyal, like Maija, who came alone simply because she wanted to support me in this new adventure after working together a decade ago. They were brave, like Kathleen, who booked herself in solo because she needed a break from the relentless noise of modern life.

From 45 to 75, these women were active, open-minded, and led with open hearts. They reminded me exactly why Girl Trips exists.

The Women Behind the Scenes

And then there were the women who made this trip possible.

Lisa from Le Boat cruised along with us for a couple of days and organized a harvest feast at Poonamalie Locks on our final night. Cynthia from Life is Good in Westport created VIP badges that gave everyone 15% off at shops around town, adding a touch of whimsy and excitement to our stop.

Allison at Scheuermann Winery walked me through how to host a big meal like this for the first time, and Amy from C’est Tout provided a spectacular kickoff lunch and the most heavenly pastries for breakfast the next morning.

And Jeanette? Do you want me to cry? She’s already one of my favourite humans, but working alongside her on this trip only deepened my love and respect for her. Her energy set the tone for the whole experience.

Yeah. This trip was about women from start to finish.

It reaffirmed what I’ve known all along: Girl Trips is where wanderlust meets sisterhood.

I’m deeply and profoundly grateful that these women have come into my life.

The Setting

Westport, Ontario, is like something out of a Hallmark movie, but with better wine. Its charm made it easy to slow down and actually be present. There’s something about pretty streets, good food, and water views that softens everyone’s edges.

(If you want to read more about Westport, I wrote about it over on Life in Pleasantville.)

The Small Touches

I treated my guests the same way I treat my closest friends. Homemade goodies, thoughtful little gifts, a few surprises tucked in, and zero pretense. Realness matters. When people feel cared for, they relax. And when they relax, they connect.

What Surprised Me Most

Honestly? How quickly the group gelled. I had expected polite small talk at first, maybe a slow warm-up. What I got was instant camaraderie.

Also surprising: how right it felt. After two and a half years of imagining this, the reality was even better. I didn’t need to manufacture connection; I just needed to create the container for it.

Looking Ahead: More Girl Trips, More Connection

This first trip reminded me why I started all of this. Women are craving spaces like this. Spaces that are warm, welcoming, a little whimsical, and designed for genuine connection.

If this story has you nodding along, there are a few ways to join in:

• ✨ Sign up for the Girl Trips newsletter to get first dibs on upcoming trips.
• 🎄 Check out the Christmas in the Valley getaway Think cozy B&B, festive towns, gourmet dinners, and a Christmas pajama party with new friends.
• 💬 Or just follow along and keep this on your radar, because I’m just getting started, with six trips/events planned for 2026!

Girl Trips isn’t just about travel. It’s about giving women the space to find each other again. And if the first girls trip in Canada is any indication, this is only the beginning.