THE WEEK AWAY

Hi, I’m Steph.

I’m the type of person who checks Google Flights for fun and starts planning the next trip before the current one is over.

As of 2026, I’ve visited 38 countries, but my love of travel didn’t really start with the destinations—it started with the planning.

Our Family

I’m married to Kyle, and together we’re raising our three kids—Gwen, Millie and Archie—in Winnipeg, Canada. Most of the itineraries you’ll find here have been tested by our family of five.

It All Started With a Solo Trip to Europe

When I was 22, I booked my first trip to Europe solo.

I had no idea how to plan a trip overseas, so I signed up for a Contiki tour. It felt like the easiest way to experience Europe, and in two weeks we visited six different countries.

That trip completely changed how I thought about travel.

Before then, I assumed you needed weeks or even months in one place to truly experience it. Instead, I discovered that with thoughtful planning, you could experience an incredible amount in just a week or two.

It also taught me something else.

Many of the optional excursions offered on the tour didn’t feel authentic. They were expensive, tourist-focused experiences that just didn’t appeal to me.

Instead, I’d organize dinners and evenings out for other people on the tour who wanted something more local. We’d find neighbourhood restaurants, wander side streets and experience the city in a way that felt much more genuine.

Then Life Changed

After getting married and having our first daughter, travel looked different.

Like many young families, we gravitated toward all-inclusive resorts because they were easy. We even stayed at the same resort in Mexico five different times.

It was relaxing, but eventually we realized something.

We were seeing the resort.

Not the destination.

Fast forward to 2018 and our third child was born.

Suddenly, we were a family of five—and that simple fact changed everything.

We no longer fit comfortably into a standard hotel room, and most all-inclusive resorts required us to book two rooms or pay for an expensive suite.

That’s when Airbnb entered our lives.

At first, it was simply the most practical option.

It quickly became our favourite way to travel.

How We Plan Our Trips

Over the years, we’ve figured out what kind of travel makes our family happiest. It isn’t about seeing the most attractions or checking famous landmarks off a list—it’s about experiencing a destination at a pace that actually feels like a vacation.

Most of our trips are between seven and ten days. We’d happily stay longer, but between work, school, and everyday life, that’s usually the amount of time we have. The good news? We’ve learned that with thoughtful planning, a week is plenty of time to experience a place without feeling rushed.

Whenever it’s practical, we rent a vehicle. For a family of five, we’ve often found that an airport shuttle alone can cost nearly as much as renting a car for several days. Having our own vehicle also gives us the freedom to discover hidden beaches, stop at scenic viewpoints, and explore small towns that many visitors never see.

With very few exceptions, we stay in Airbnbs. Partly because five people don’t fit comfortably in a standard hotel room, but mostly because we’ve grown to love the experience. Having a kitchen means relaxed breakfasts before heading out, easy snacks for hungry kids, and the occasional homemade dinner after a busy day exploring. It gives us the flexibility to spend our money where it matters most to us.

While we enjoy sightseeing, we’re just as happy spending an afternoon at a quiet beach, wandering through a local market, or discovering new towns. We don’t believe every minute needs to be scheduled. Some of our favourite travel memories have come from slowing down and simply soaking in where we are.

You’ll rarely find us at an all-inclusive resort. We’ve found that not having every amenity at our doorstep means we naturally spend more time exploring neighbourhoods, eating where the locals eat, and authentically experiencing the destination itself.

One of the biggest surprises? This style of travel is often less expensive than people expect. By combining vacation rentals, rental cars, and local restaurants, we’ve been able to create unforgettable family trips that cost less than many traditional resort vacations.

If our travel style sounds like yours, I hope the itineraries, budgets, and guides on this website help you plan a trip you’ll remember for years to come.

My Favourite Part? The Planning.

I genuinely love trip planning.

I love comparing flight routes.

I love watching Google Flights and perusing Google Maps.

I love finding incredible Airbnbs.

I love arranging airport transfers before we arrive.

I love discovering experiences that cost little or nothing.

I love maximizing travel rewards through credit card points.

We use travel rewards extensively and often book our flights with points. Over the years we’ve learned when points offer incredible value—and when paying cash is actually the better deal. I’ll be sharing those strategies here, too.

For me, planning isn’t something I have to do before a trip.

It’s part of the fun.

Why I Started This Blog

For years, friends, family and even complete strangers kept asking me the same questions.

“How do you afford to travel so much?”

“Where should we stay?”

“How did you find that Airbnb?”

“Can you help me plan my trip?”

Eventually I realized I was answering the same questions over and over again.

This blog is where I share the itineraries, budgets, accommodations and travel tips that have worked for us over the years.

If you love authentic destinations, beautiful accommodations, finding incredible value, and coming home feeling like you truly experienced a place—not just visited it—I think you’ll feel right at home here.