As someone who has worked in travel and hospitality for almost a decade now, I’ve learned from colleagues, friends, and my own experiences that audiences are very split between a well-planned vacation and a holiday where the need to let go of rigid rules overpowers the desire for a thoughtful itinerary. Working closely with storytellers at some of the top PR agencies in Toronto has also shown me just how differently people approach their time off. Vacations can be the highlight of our year but planning them often falls to the bottom of our to-do list. We daydream about sandy beaches, bustling markets, or long-awaited adventures, yet many of us don’t take the steps needed to turn those dreams into the kind of trip we’ll reminisce about. Thoughtful vacation planning isn’t just a nice-to-have. It’s the difference between your average getaway, bordering on the mundane, and a truly spectacular adventure that stays with you for years to come.

Ahead of vacation planning season, I learned that that travel expert, seasoned storyteller and one of my favourite travel journalists, Doug Wallace is now the author of the newly released How to Plan a Vacation. Wallace has spent years helping friends, relatives, and countless readers avoid the common pitfalls that derail a great trip. With Wallace’s new book now a resource for novice and well-travelled explorers, it was the perfect moment to ask him about the inspiration behind his guide, the myths around spontaneity, and the small but powerful planning habits that can completely transform a holiday.

From the Q&A below, I hope we reveal how much more enjoyable travel can be when you understand the “shape” of a well-designed vacation. Here’s what I learned.

What inspired you to write How to Plan a Vacation? Was there a particular trip or moment that made you realize the need for such a guide?

After years of setting my friends and family straight on how to map out the best vacation ever, or at least stop making common travel-planning mistakes, I had amassed quite a volume of advice. And after hearing so many anecdotes about people not getting the most out of their vacation—which is an expensive endeavour that necessitates myriad considerations and decisions—I decided to share what I know. Turns out, I have real, first-hand experiences to go with my planning checklist, which I hope are amusing my readers as well. I had great fun writing it!

While not for me, many travellers enjoy the spontaneity of “wing-it” style vacations. Is there still room to be spontaneous even while following the principles you outline in vacation planning in your book?

When people wing things, they really only experience a half-baked vacation—then wonder why they had a “meh” time. It’s very true that spontaneity is an essential part of travel; you have to allow yourself the room to wander at will and indulge your curiosity. But that time for improvising has to be slotted in somewhere. “We’re going to the spice market tomorrow morning early, and we don’t have to do anything else until we meet up with the others at five for drinks.” There. Done. Your vacation day has to have some sort of “shape,” or things become too willy-nilly.

What do you think is the most challenging element of vacation planning that Canadian travellers most commonly struggle with?

I think the answer to this is prioritizing travel—actually getting it on the calendar and making the leap. We’re often really good at wishing we could travel more, but we suck at actually following through. I remember years ago asking a friend, “How do you manage to travel so much?” And he said: “I buy a ticket.”

How do you decide what to splurge on while budgeting your vacation – in what order do you prioritize better luxury hotels, premium flights (or direct flights) or itinerary experiences and why?

Every traveller has their own threshold for how they save and splurge. This is a very personal thing. I have a friend who only stays in budget accommodations and eats street food in order to have the money to shop. There’s a buddy who only travels in Premium Economy and doesn’t care that that costs a fortune (to me it does, anyway). I have a relative who goes completely all-out, splurging at every level, then is totally fine with staying home for long stretches between holidays. What I’m saying is: you are your own comfort leveller.

What’s the biggest or most common mistake you see people making when they plan vacations, and what simple advice would you give to avoid it?

This would have to be: waiting until they have boots on the ground before determining what they want to do. So many people schedule their time off, book a flight and a hotel—then don’t do any more research. Proper vacation planning requires homework. Not researching means you have to settle for less, because you didn’t take the time to find out everything you possibly can about your destination, so you can then make informed decisions on how to adequately spend both your time and money. We have this thing called the internet now. You need to use it.

Finally, if there is one golden rule that travellers can take from How to Plan a Vacation, what would it be?

Taking your holiday from so-so to spectacular is dead-easy if you take care of all of the little details in advance. Then when the day arrives, your holiday can just roll out smooth as silk.

In conclusion, I hope you are inspired to book the tickets and start planning for spontaneity! How to Plan a Vacation is available in ebook and print formats. Choose your favourite format via Wallace Media.