True Tales of Canada’s Funniest Family Vacations

Real Canadians answer, “What’s the funniest thing that ever happened to you on family vacation?”

1 / 7
Family vacation - pickpocket wallet
Photo: Shutterstock

The Pickpocket Dance

By Catherine Stinson

When I was seven-and-a-half months pregnant with our first child, my partner and I squeezed in a few days of vacation while in Barcelona for a work trip. Our hotel was cheap, with paper-thin walls, barely enough space to walk between the bed and the bathroom, and a view of a brick wall. But we could swim in the Mediterranean and tour the Sagrada Familia, so we didn’t mind. It was our last hurrah before becoming parents.

The hotel was just off the main tourist drag, on a dark, narrow alley. One evening, as we were walking back from eating tapas, a boy of about 16 struck up a conversation. He wanted to know where we were from and whether we liked Barcelona. It was obvious to me that his false friendliness was leading to a scam or unwanted advance of some sort, so I refused to engage and walked more quickly. But my partner allowed himself to be enveloped in a chummy shoulder embrace and ended up a few metres behind me.

When I looked back to urge him to hurry up, I saw the two of them locked in an awkward sort of dance. They had one arm and one leg wrapped around each other and were both hopping on their one free foot. I realized that the boy had my partner’s wallet in his free hand and was trying to hold it out of sight behind his back.

Without another thought, I ran over to try to grab back the wallet. The boy saw me coming and tossed it to one of his buddies, who were hanging around nearby. I continued to very pregnantly waddle-run over to that young pickpocket. It was only when I was standing in front of him and we locked eyes that I finally realized that I was perhaps doing a foolish thing. Was I going to get into a street brawl with a group of teenage boys, while so pregnant that my fists would have reached no further than my belly stuck out? He must have also seen how absurd the situation had become and tossed the wallet at my feet with a practised nonchalance. I grabbed it, and the boys scurried away.

A small crowd of passersby had gathered to watch. Two sex workers came over to praise my street smarts.

My partner lost a bit of his pride in that Spanish alley, but at least he didn’t lose his wallet.

Learning these pickpocket secrets could save your vacation.

2 / 7
Family vacation - shirley temple cocktail
Photo: Shutterstock

I’m Raising a Barfly

By Leah Rumack

My eight-year old son, Ben, is obsessed with sitting at bars. He loves nothing more than to have a drink while perched on a stool. It could be because his dad is a craft-beer nerd—and Ben wants to do everything that Daddy does. But the only times Ben is somewhere where kids are allowed to sit at the bar is when we’re on family vacation at a resort or on a cruise. That boy has sampled all the best virgin cocktails from Mexico to Amsterdam.

Last summer, we took a river cruise down the Rhine, and despite the fact that we were surrounded by castles and incredible medieval towns, Ben’s favourite part of the experience was the nightly cocktail hour. Every evening, he made sure we were right on time for “Sip ’n’ Sail,” where he planted himself on a bar stool and ordered Shirley Temples. A river cruise means travelling on a small ship, and there were only about five spots at the bar in total, but that was his seat.

At the end of our trip, when we passed through Canadian customs, the agent didn’t believe us when we told her we didn’t buy anything while we were away. So she turned to Ben and asked: “What about you? Did they buy you anything?”

“Just a lot of cocktails!” he replied.

3 / 7
Family vacation - hot pepper
Photo: Shutterstock

Beware the Pepper

By Stacy Lee Kong

Every summer, my family takes a day trip to Turkey Point, a beach in Norfolk County, Ontario. A motley—or at least loud—crew of parents, siblings, kids and in-laws, we try to make these excursions feel like beach days in Trinidad, where we’re from. We always have pelau, a meat-and-rice dish that somehow became the traditional beach meal for the entire country. A true Trinidadian, my auntie Pat always adds a whole hot pepper to the pot.

Well, one year, the inevitable happened. My brother-in-law Dave is not Trini—he’s white and was born in Canada… And he’s not a fan of spicy food. That’s why we made sure to warn him not to eat the pepper. And he said, “I know not to eat the pepper!”

And then? He accidentally ate the pepper.

For a second, we were all frozen, watching in shock as his eyes watered and his face turned sunburn red. Then everyone started talking at once. I have never seen so many grown adults say so much and accomplish so little. I started googling remedies for spicy food, as if milk or bread were going to magically turn up on the beach. My mum was trying to force him to drink water, even though we all knew it wouldn’t really help. And my sister Sharon, Dave’s wife, was laughing hysterically while she sliced up an avocado in hopes that its creamy qualities would act like milk and soothe the burn. Luckily, it did help.

And guess who never ate a pepper again?

4 / 7
Family vacation - glass of wine in cabin
Photo: Shutterstock

My Wife’s First (and Last) McBride Family Vacation

By Jason McBride

After my girlfriend, Liz, and I had dated for about a year, and a few years before we got married, she joined me, my parents and my sister’s family on a ski trip in Stowe, Vermont. I was in my late 30s, it was the first family vacation I’d been on in years, and it was the first such holiday Liz had ever taken with my relatives.

But a ski vacation is only as good as the ski conditions, and that January was spring-like. To make matters worse, our rented cabin was close to the ski hills but far from anything else. There was no Internet, and the only entertainment was a few board games and a single television.

For a couple of days, while we waited for the snow to fall, we watched endless hours of CNN (mom’s choice) and SpongeBob SquarePants (my six-year-old niece’s), played Scrabble and drank. Cabin fever set in quickly. At one point, my mom literally fought my niece for the remote control, even sitting on her to wrest it from her hands. My brother-in-law was downing a bottle of port and a bottle of white wine nightly. Amazed, but also alarmed, Liz confronted me in our bedroom: “What is wrong with your family?” I remember well her crazed laughter as she said it.

Then it snowed, but only at the top of the mountain—a very tall and fearsome peak. We scrambled, drove to the lift, took it up. But as we climbed higher into quiet, dense cloud, Liz began to look uneasy, then terrified. When I asked her what was wrong, she revealed that her skiing experience was… Limited. “I’ve only ever been on a bunny hill,” she said, clutching my arm. “A bunny hill!” The lift let us off at the summit of a double-black-diamond ski run in the middle of a snowstorm.

My family, with nary a look back, disappeared down the hill. Liz got off the lift, just barely, and then, two falls later, took off her skis and promptly got back on the lift, taking it back down to the lodge and the relative safety of a large glass of wine.

Did I say it was her first vacation with my family? It was also her last.

5 / 7
Family vacation - woman sitting on dock at cottage
Photo: Shutterstock

The Family Vacation of My Dreams

By Leah McLaren

I often imagined the sort of family vacations I’d have when and if I was ever lucky enough to become a mother. These fantasies were unspecific, idealized versions of my own childhood summers, which mostly occurred on boats or at cottages in Ontario and Quebec in the 1980s. In my mind’s eye, I’d skip over the maternity bathing suits and squalling infants with heat rash—and get right to the fun part, where I sat on a dock, reading a novel and sipping a gin and tonic while my children frolicked joyfully in the water.

A few years later, my dream came true. Well, sort of. My husband, our three-year-old son James and I rented a cottage in North Hatley, Quebec for the entire month of August. I’d finally live my cottage dream! What could possibly go wrong?

For one thing, James couldn’t swim, which wouldn’t have been a problem if he wasn’t such an avid water-sport enthusiast, hurling himself into any pool or lake with all the foresight of a Labrador going after a stick. The first three nights I was so terrified that I made him sleep in his life jacket.

Instead of letting me sit on a dock with a book and a drink, James wanted to canoe and kayak, to mountain bike and windsurf, and play every single board game on the cottage shelf. The fact that he lacked the cognitive development or motor skills to do any of this in no way deterred him from insisting that he absolutely must. And then when he tried and found he couldn’t… The outrage! He howled and screamed and shook his tiny fist at the gods. Why was it so hard being three? Someone was going to have to pay. By which, of course, he meant me. The one who’d brought him on this hellish ordeal known as a “family vacation.”

Luckily there was one thing that mollified my toddler: peanut butter bagels. So for the rest of the holiday, that’s all he ate—for breakfast, lunch and dinner, nothing but peanut butter bagels. Occasionally I’d throw in a Popsicle or an ice cream sandwich for variety.

In other words, I gave up. I guess you could say I failed. But guess what? My son, who’s now seven, still claims to vividly recall that family vacation. “Remember the summer when you let me eat nothing but peanut butter bagels?” he’ll say, sighing nostalgically over his plate of steamed broccoli. “That was the best summer holiday ever.”

Don’t miss these funny tweets every parent can relate to.

6 / 7
Family vacation - paddling canoe
Photo: Shutterstock

Houseboat Follies

By Megan Murphy

By the glow of a hurricane lantern, my dad read another chapter of Moby Dick to my mom, two sisters and me—a nightly ritual aboard our rental houseboat: “I love to sail forbidden seas and land on barbarous coasts!” he recited.

It was the summer of 1990, and my folks had the inspired idea to spend our week’s holiday making memories while cruising the lakes and canals of Ontario’s Trent Severn Waterway. My mom pictured Norman Rockwell. My dad, Captain Ahab.

My parents were not, unfortunately, adept boaters, and steering a 12-metre housing unit into a lock, next to million-dollar cruisers, tested their marital vows.

“Mary Anne, tether the rope to the wall! Our back end is drifting!” my dad shouted as he manoeuvred us into lock 34, near Fenelon Falls.

“I’m tethered, Marty! And do you seriously think I can pull a thousand-pound boat by myself?” Each lock was another divorce near miss.

One night, we heard a commotion at the back of our boat. Was it a great white whale? Not quite. A couple of young hoodlums were attempting to burgle our yacht! My typically mild-mannered father gave chase while my mom yelled after him: “And just what do you plan to do if you catch them, Marty?”

They managed to escape, but to my 11-year-old eyes, it was all very heroic.

Another day, we moored on a little island, romantically assuming it would be our own private oasis. “Touch nothing and get back on the boat!” my mom shouted when she realized the island was covered in poison ivy.

The following morning, my dad backed the boat into a rock shelf, breaking the propeller. Fortuitously, he had “packed” a canoe, which was hauled down from the top deck. My older sister and I paddled with him to shore for prop assistance, leaving my mom and younger sister behind to say the rosary.

The houseboat, and all five crew, made it through the week in one piece, (not counting the half prop). The family vacation didn’t go as planned, but my parents did get what they wanted—a trip worth remembering!

7 / 7
Family vacation - restroom sign
Photo: Shutterstock

Toilet Tosca

By Craig Baines

When my sister was 13 and I was nine, Mom and Dad took us to Barbados, where they had honeymooned 20 years earlier. One evening, Dad decided to take us out for a special supper at a romantic spot where he and Mom had dined as newlyweds.

By that point in our trip, my sister and I were oscillating hourly between being the best of friends and the worst of enemies. As we got out of the car, Mom cautioned us: “Now you are both to be on your best behaviour tonight. I don’t want any scenes!” (She’d used her teacher’s voice, and you didn’t want to mess with that.) “We’re fine,” we chirped.

The restaurant’s outdoor terrace was pretty full, mostly with couples chatting quietly across candlelit tables. The hostess sat us at a spot right in the middle and handed us each a giant menu. We were the only family there. Mom and Dad exchanged smiles. Mom leaned over her menu and whispered: “Isn’t this nice?”

My sister shrugged. I got up to find the washroom. The hostess guided me to a door of the main building and told me I’d find the restroom upstairs. The stairs were dark, and they took a couple of turns before I finally made my way to the top. I opened a door and stepped into a brightly lit bathroom. I realized I had the place to myself, far away from the diners. I needed relief, and I needed it fast. I just had to let it out.

It’s not what you’re thinking.

You see, for the past week, a jingle for a leading brand of Canadian bathroom tissue had been rattling around in my head. The ad praised the gentle texture of the three-ply tissue while a model lightly rubbed her cheek with a whole roll of it. I assumed this was something models did in their free time.

I stood before the mirror, cleared my throat and took a deep breath. Raising my arms like an orchestra conductor, I sang at the top of my voice: “You can feel the cottony softness!” As the reverb subsided, I thought, Hmm, not bad at all.

Stepping back onto the terrace, I noticed a couple watching me as I passed them. When I reached my family’s table, I sat down and spread my napkin across my lap. My dad and sister were hunched over their menus, hiding their faces. I looked over to Mom. She was glaring at me.

“What?” I asked.

“Craig, where were you just now?”

“Washing my hands,” I said. “In the bathroom.” (Duh.)

“You mean that bathroom?” Mom pointed to a window open to the terrace. My eyes widened.

I looked over to my sister. She rolled her eyes.

“You big dummy,” she said.

Next, check out these hilariously awkward funny family photos.

Reader's Digest Canada
Originally Published in Reader's Digest Canada

Newsletter Unit