I’m Tara Cannon and I have been running Pint Size Pilot ® since 2012 (and another little site before that).

My husband Rann and I have been traveling with our two kids, Lucas and Ella, since they were wee babies from our home base of Vancouver, Canada.

Prior to having children, we were very enthusiastic world travelers and figured that having a couple little people along for the ride wouldn’t have to change anything.

Now, of course it did, but we still managed to have amazing adventures all over the world – just doing things a little differently than we had before. (Hint: We had to slow our travel pace down a bit.)

Tara Cannon
In Argentina – A day before I found out I was pregnant with #1.

How it Began

I started Pint Size Pilot family travel website because I wanted to share what we had learned along the way and to encourage and support other parents wanting to have grand adventures of their own.

I believed (and still believe), that just because you have kids in tow, this does not mean that your travels have to be limited to theme parks and all-inclusive resorts. It can be done a different way.

Pint Size Pilot
2012 in Tortola at a delicious BBQ joint called “Hog Heaven”

In the beginning, I tried to focus on some of the most challenging aspects of travel with a baby or toddler. I created guides on topics such as planning a first family vacation and tips for flying with kids.

Back then, our travels were primarily taking us to island destinations in the Caribbean (Anguilla, Saba, Barbados, St. Barts, Terre-de-Haut and more). Coming from the west coast, however, our travel time was often 24 hours our more, involving several stopovers.

First tortoise sighting in the Grenadines.

While it seemed to take forever, eventually a day came when we could leave all the cumbersome baby gear behind. Goodbye travel stroller!  Good riddance travel car seat! We felt so free.

With only a travel booster seat or two, things became so much easier. I still remember strapping our daughter into her seat for the craziest ride over a mountain pass to access Panama’s rather remote Guna Yala Islands. She only threw up twice (poor girl has always struggled with motion sickness). It was a bit of a crazy adventure, but totally worth it.

Panama with Kids
The San Blas Islands (Guna Yala), Panama

City Escapes

When our kids reached an age where they could start fully enjoying some city breaks, I put my energy into creating in-depth family travel guides to some of my favourite cities (Paris, New York, Reykjavik, Austin, Victoria and Oslo).

I tried very hard to not only cover the main tourist attractions but to also find some more immersive experiences – whether it was a kids’ pastry class in Paris, a museum sleepover in NYC, or a visit to a geothermally-heated beach in Reykjavik.

Paris with Children
Cook’n with Class – Kids’ Pastry Class Paris
Iceland with Kids
Nautholsvik Geothermal Beach – Reykjavik, Iceland

Unique Hotels

I have always had a passion for unique and special accommodations. Some of our unusual stays have included a treehouse in Oregon, a caboose in Nova Scotia, a lighthouse on Prince Edward Island, and a vintage trailer park in the Willamette Valley (OR). The odder, the better for this family!

Lighthouse Hotel – Prince Edward Island, Canada

We have also been lucky enough to stay at some really extraordinary hotels and lodges around the world.

I don’t know if there is an official term for our travel style (I call it high-low travel). Even before kids, we would frequently choose a modestly-priced place (usually a vacation rental) for most of our trip and then splurge on a very special stay for a couple nights at the end.

We have had some pretty amazing stays around the world – from a private island in Northern Norway to an exceptional lodge on Fogo Island in Newfoundland, Canada.

Manshausen Island Resort, Norway
Manshausen Island Resort, Norway

The most interesting thing to me about the places we have stayed over the years, has been that for my kids, there has been little correlation between how much they have enjoyed a place and the price.

Glamping in Iceland
Glamping – Vestmannaeyjar, Iceland

When we reminisce about our best trips, a treehouse that was $150/night will be right up there with a luxury lodge in Ecuador. Any place where they were able to build a fire gets bonus points (hello camping).

I’m not going to lie though…I absolutely love the special properties (I’m a terrible camper)! Click the link to see some of our favourite unique lodges around the world.

Fogo Island Inn – Newfoundland Canada
Fogo Island Inn – Newfoundland Canada

The Bucket List Stuff

Eventually, we were able to start ticking off some bigger bucket list items – like our first big jungle adventure trip to Panama, followed by Machu Picchu, The Galapagos, the Atacama Desert and even the blue ice caves of Iceland. On one crazy trip we even did a ski trip to Chile during our North American summer.

Note: Although I hate waiting, we deliberately put off visiting some of these destinations until we felt that our kids were old enough to fully enjoy, appreciate and actually remember the adventures.

Some of the experiences we wanted to have as a family also required that the kids be of a certain age. I pretty much had a minimum age to visit travel schedule tattooed to my arm.

Galapagos with Kids
The Giant Tortoise – Galapagos, Ecuador
Ice Cave Tour, Iceland
Blue Ice Caves, Iceland
Pint Size Pilot Family Travel Adventures
A Rare Family Photo – The Sacred Valley, Peru

We Are Ski Tourists

We are and have always been ski tourists. What I mean by that, is that we love trying out a new mountain each season, when possible.

In recent years, we have been lucky enough to explore numerous slopes in the U.S. including Telluride (CO), Jackson Hole (WY) and several resorts in Utah (Alta was our favourite).

Closer to home in Canada, we like to visit Whistler, as well as interior favourites SilverStar, Red, Revelstoke and Kicking Horse).

Jackson Hole with Kids

Wilderness Adventures

We have also always been absolutely bananas for special wildlife viewing experiences. Nothing will have us leaping out of bed at 4:30am like the opportunity to see parrots feeding on a clay cliff in the Peruvian Amazon or a pod of dolphins frolicking in the sea in Puerto Escondido, Mexico.

Dolphin Watching Tour – Puerto Escondido
Puerto Escondido, Mexico

Staying closer to home in British Columbia during the pandemic allowed us to see our first black bear in the wild. Naturally, this made us want to see more bears – later planning a grizzly bear watching trip to B.C.’s Bella Coola Valley.

BC Grizzly Bear Tours
Grizzly Bears in the Bella Coola Valley

I have such grand plans for our future wildlife adventures. I am desperate to swim with whale sharks off of the Ningaloo Reef in Australia, I’m dying to watch the Great Migration in the Serengeti and I’m dreaming about kayaking with beluga whales in northern Manitoba, Canada.

A Hiking Family

Back when international travel was curbed, we slowly became a hiking family (the perfect distanced activity). We started off slowly with some easy hikes near Vancouver and slowly progressed towards bigger ones.

Whitecap Alpine Hiking
Whitecap Alpine – British Columbia

Now with teens in our lives, I find that hiking is great for conversation. In somewhat unsettling and confusing times, it’s nice to be able to tap into where their heads are at (and explain to them that Instagram and TikTok are not great news sources).

Pint Size Pilot
Iceland Westfjords (2023)

Where Next?

In 2024 our travel plans include Brazil, Norway and Peru!

Let’s Connect

While a lot has changed over the years, one thing that has stayed the same is how much I love helping with and hearing about your travel plans.

Want to connect? Please feel free to reach out to me on Facebook, Instagram or by email at [email protected].

I also wanted to share with you this little video of some of our adventures. I hope it provides you with some travel inspiration. Yes, you can have grand adventures with kids in tow! We are living proof!


Update: In 2022 I created a second site called The Better Beyond with a focus on responsible travel. See also my latest posts on Instagram and Facebook.