Girl Talk

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

Girl Talk

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?

Friends forever or new friends? I’m not telling.

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?

Our final night at Poonamalie Lock was magical.

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.

The Sanity-Saving Power of Planning Joy

Girl Talk

Here’s how my girlfriends and I keep it together: we never leave one trip, brunch, or birthday without another thing in the calendar. Always. Even if it’s months away. Even if it’s small. Especially because the world feels like it’s spinning faster every day. We hold on to joy with both hands—one reaching back to the memories we’ve made, the other stretched forward to whatever’s next. That next dinner, that next retreat, that next chance to exhale and just be. It’s how we stay sane. It’s how we stay connected. We always have something to look forward to…..and that’s everything.

always have something to look forward to with your friends

Why Always Having Something to Look Forward To Works

We weren’t always this intentional. But after a few chaotic years, we realized we needed anchors. Not just big annual getaways or milestone birthdays, but little moments to anticipate—a weekend hike, a seasonal picnic, a randomly themed event, even a wine-fuelled planning night for a future trip. Turns out, anticipation is a form of therapy. It lifts you out of the day-to-day grind and gives your brain something hopeful to chew on.

Plan themed parties with friends and always have something to look forward to in you calendar

Our Rule: Never Leave Without a Plan

It started as a joke: “Okay, when’s the next thing?” But now it’s gospel. We don’t end a gathering without putting the next one on the calendar. Not a vague “sometime in the fall” plan, but an actual date, time, location—locked in. It’s like leaving yourself a trail of breadcrumbs, reminders that the good stuff isn’t behind you, it’s ahead, too.

A group of friends together in the summer on the beach

The Psychology of Anticipation

There’s science behind this, by the way. Studies show that looking forward to something activates the reward centre in your brain—releasing dopamine, improving mood, and reducing stress. Some researchers say the anticipation can be just as powerful as the event itself. (So yeah, planning that fall retreat? Already good for you.)

Group of women whitewater rafting on a Girl Trip — adventure to look forward to

How Girl Trips Help Us Hold On

Girl Trips was born from this very practice. The need to plan joy into our lives. To have a circle of women who don’t just show up when it’s convenient, but who plan for connection. Whether it’s a full-blown retreat, a girls’ weekend in the woods, or a cozy winter dinner party—what matters most is that it’s in the calendar. It gives us something to look forward to together.

Ideas to Add to Your Calendar Today

  • A weekend road trip to somewhere none of you have been
  • A themed dinner party (bonus points for dress codes or potlucks)
  • Booking a seasonal Girl Trip retreat (hint, hint)
  • Monthly wine + vision board night
  • A Sunday morning walking club
  • Join a Pickleball league, all the cool kids are doing it

Doesn’t have to be big. It just has to be there.

Women on a Girl Trip relaxing on a boat — always have something to look forward to

It’s Not Just a Trip, It’s a Lifeline

In this world of burnout and bad news, joy has to be intentional. My girlfriends and I plan for it. We put it in our calendars like it’s a dentist appointment—non-negotiable. And you know what? It works. We hold hands across time, past and future, joy to joy. If you’re reading this and thinking, “I need that,” then maybe your first step is the same as ours: book something now. Give yourself something to look forward to.

What Is Shiggles? A Word for Living a Little Freer

Girl Talk

There’s a word I use a lot: shiggles. It’s a mash-up of shits and giggles, and honestly, it’s the perfect way to explain many of the choices I’ve made in my life. Shiggles, for lack of a formal dictionary definition, is when you decide to ditch your to-do list and go hiking instead. It’s jumping in the car to see your girlfriends because—why not? It’s leaping out of a perfectly good airplane just to say you did. It’s not reckless (although in my youth, it accounted for some questionable decisions), but rather the pursuit of joyful chaos. A way to keep monotony from taking root.

Shiggles are what happens when you stop taking life so seriously.

What is Shiggles? A definition and way of life

While I have zero interest in being anyone’s life guru, I do think this particular philosophy is one more of us should adopt—because some of the best things in life happen when you just go with it. When we chase curiousity, instead of stifle it.

Things I’ve done for the shiggles:

A woman who has jumped out of a plane following a shiggles philsophy


I want more people to trust the pull toward fun, toward connection, toward something a little unhinged but entirely yours. Sometimes it’s no thoughts, all vibes. Sometimes it’s I’m doing this for the plot. Sometimes it’s signing up for a trip with women you’ve never met on the Rideau Canal (insert shameless self-promotion here). But most of the time, doing something for the shiggles is simply acknowledging that life is entirely too short to take so seriously.

I mean, look around. Things are kind of a mess. And while I’m not saying we should ignore serious issues (I’m not that far gone), I am saying it’s essential—for our mental health and for the collective well-being of humanity—that we take breaks from the doomscroll and do something fun. Something that makes us laugh, leaves us awestruck, or connects us to someone we didn’t know a few hours earlier.

A woman in a bathtub drinking wine and doing it for the shiggles

What I love most though about shiggle-fuelled decisions is that they come with no expectations. There’s no big payoff you’re chasing. No pressure to make it “worth it.” It’s just a shrug, a smile, and a “let’s see where this takes me.” That’s where the real magic tends to show up.

Doing it for the shiggles has taken me on road trips I’ll never forget, to new friendships that changed my life, and to belly laughs that still echo when I think about them. Shiggles don’t require a plan. They just require you to say yes when your soul nudges you to do something a little ridiculous, a little brave, and a lot of fun.

A woman in a Barbie box making fun of her situation

So if you ever find yourself overthinking, frozen in indecision, or stuck in the same old routine… maybe ask yourself: What would I do right now if I was just doing it for the shiggles?

Then go do that. (And maybe this)

Why I’m Choosing Canadian Destinations (and I Hope You Will Too)

Girl Talk

There was a time when I would have happily hopped across the border for a getaway. But lately? Between the rising tension toward Canadians (what did we ever do to you, America?), the weak exchange rate, and the growing list of reasons to stick closer to home, I’m leaning in hard to Canadian travel for women.

A woman on rocks overlooking Gypsum Mine in Cape Breton Island talking about Canadian Travel for Women

And honestly, I’m not mad about it.

I mean, why would I be? Canada is incredible. We’ve got landscapes that look ripped from a postcard with enough space to explore without crowds. We’ve got hundreds of tucked-away towns, scenic stretches of road, crystal-clear lakes, cozy cafés, and enough starry skies to make you forget your phone even exists. Bottom line? You don’t have to go far to feel like you’ve truly gotten away.

Ingonish Beach Cape Breton Island

Why Canadian Travel for Women Matters

Women make up the majority of the tourism workforce and the bulk of travel decision-makers. So when we choose to explore Canada, we’re not just saving on airfare, we’re fuelling our own economy. Girl Trips is committed to booking tours and experiences run by women wherever possible, buying local goods, and bringing in yoga instructors, artists, chefs, and guides who live right here. Supporting women and Canadians in tourism doesn’t always have to look like a TED Talk or a LinkedIn post, sometimes it looks like a girls’ weekend in Muskoka.

Peggy's Cove with a woman wearing a lobster sweater, promoting Canadian travel for women

One of My Favourite Place? The Rideau River

Our first getaway, the Retreat on the Rideau (happening September 19–22, 2025) is the perfect example of why Canadian travel is so special. Picture this: four boats, a flotilla of fantastic women, cruising the historic and iconic Rideau Canal from Smiths Falls to Westport. There’s yoga on deck, delicious meals (including dining al fresco and a vineyard dinner), and just enough small-town charm to remind you why you never have to leave our amazing country.

Captain of a Le Boat on the Rideau Canal

This trip is equal parts adventure and exhale, and the best part? No airport security lines required.

Bottom line? Canada has everything we need—beauty, connection, and women doing cool sh*t across every province and territory. So if you’ve been dreaming of a meaningful escape, start by looking right here at home.