The Year We Couldn’t Stop Booking Trips

Some years feel full. Then there was 2025, the year we somehow stretched four weeks of vacation into what felt like an entire year of travel.

A big part of it came down to learning how to plan around Canadian long weekends, school holidays and the vacation days we already had. We did not take months away from work or completely rearrange our lives. We simply became much better at finding the extra day or two that could turn a regular weekend into a real escape.

February kicked things off with the longest journey of the year. We finally took Pierce on the 18-hour flight to Hong Kong to visit my family and added Tokyo to the same trip. By pairing it with the Family Day long weekend, we gained just enough extra time to settle in without using more vacation days. Pierce handled the flight so well that, as we were getting ready to leave the plane, a passenger turned around and said, “I didn’t even know you had a baby with you!” That pretty much set the tone for the year.

In April, we travelled to San Diego for a Disney cruise and tied the trip into the Easter long weekend. It felt like the perfect break before spring really began at home, and it marked the start of what would become a surprisingly busy travel season.

Not every memory required getting on a plane. Once summer arrived, we spent time at a cottage in Blue Mountain with friends. It was one of those easy weekends filled with good company, fresh air and a slower pace. It reminded us that getting away does not have to mean going very far. We also made it to Canada’s Wonderland with Pierce. Watching familiar places become new again through his eyes has been one of my favourite parts of travelling with him, even when the “trip” is only a drive from home.

In August, we found ourselves taking a spontaneous trip to Las Vegas, thanks to the Civic Holiday long weekend. Las Vegas with a toddler may not sound like the obvious recipe for relaxation, but somehow it became one of the most relaxing vacations we had all year.

We returned to San Diego in September, this time taking advantage of the Labour Day long weekend. Pierce lived his best life digging in the sand and running into the waves as though he owned the beach.

As the weather cooled, we spent more time at our own cottage with friends. Those fall weekends felt different from our summer travels. They were quieter, cosier and less planned. They gave us time to slow down between trips and enjoy being together without an itinerary or somewhere else to be.

In November, we sailed out of Miami aboard Icon of the Seas. That trip did not line up with a long weekend, but we made it work anyway. Sometimes the timing is not perfect on paper, but you go because it feels right.

We ended the year in Porto, Portugal, where we spent a week with my parents during the Christmas holidays. Portugal is the place we continue to return to. There is something comforting about going back to a destination that feels familiar while still giving us something new to discover each time.

Looking back, 2025 was not only the year we could not stop booking trips. It was the year we became more intentional about fitting travel into the life we already had. One promise we made to ourselves early on was that having Pierce would not mean losing the parts of us that loved exploring the world. We still wanted to spend time together, keep travelling and bring him into our lives rather than making our lives smaller around him. So far, he has loved every moment.

Travelling with a toddler is not always effortless, but with the right expectations and planning, it has been much easier and far more rewarding than we imagined. Whether we were flying across the world, spending a weekend at the cottage or watching Pierce run toward the waves, the best part was getting to experience it all together.

Now we are looking ahead to 2026 and wondering where the next long weekend might take us.

What was the most memorable trip or simple weekend away you took in 2025?