A question that’s been surfacing more frequently in recent months – particularly given the circus unfolding south of our border – is whether Wheel & Anchor might organize more trips within Canada. It’s a thoughtful request, and one I take seriously. After all, who wouldn’t want to explore the staggering beauty of our own backyard with like-minded travellers?
The short answer is: yes, we’re thinking about it. The longer answer requires a bit of honesty about why organizing travel in Canada presents challenges that might surprise those who assume “domestic” means “easier.”
Over three decades in this industry, I’ve organized a small handful of Canadian trips. None of them have been simple. That’s not a complaint, I pride myself in confronting a good travel challenge, but it’s worth explaining why planning a journey through Canada often feels harder than planning one through, say, Portugal or Poland.
Start with the obvious destinations: Banff, Churchill for polar bears, the rugged grandeur of Newfoundland. These places are spectacular for good reason, and the world knows it. The challenge is that during their prime seasons, international tour operators with massive buying power have locked up hotel inventory, train seats, and wildlife viewing slots months—sometimes years—in advance. What remains for smaller, “boutique” operators like us often comes with eye-watering price tags that reflect scarcity rather than value.
This isn’t unique to Canada, of course. Overtourism plagues destinations worldwide. But the scale and seasonality in Canadian hotspots create a particular squeeze: brief windows of ideal weather, limited infrastructure in remote locations, and fierce competition for a finite number of beds and experiences. When a giant European or American operator books out an entire lodge for the season, there’s simply no room at the inn for the rest of us.
Then there’s the geography. Canada is vast, the second-largest country on earth we like to remind others, which means distances between destinations can stretch budgets and itineraries in ways that European travel never does. A “short hop” in Canada might cover the same distance as crossing three European countries. Connecting smaller communities with reliable transport, finding quality accommodations in places without international hotel chains, and ensuring seamless logistics across time zones and provincial jurisdictions requires a level of coordination that can feel outsized compared to the final guest experience.
There’s also an economic reality that surprises many: travelling in Canada is expensive, often more so than travelling abroad. Domestic flights can cost as much as transatlantic ones. Hotels in popular areas command premium rates during high season. Meals, activities, and ground transport reflect Canadian labour costs and the challenges of operating in regions with short tourist seasons and long, quiet winters. When members compare the cost of a week in the Rockies to a week in the Alps or the Andes, the arithmetic can feel counterintuitive.
But here’s the important “but”—the one that keeps me thinking about Canadian travel despite these hurdles: just as we’ve built Wheel & Anchor programs around exploring less-trampled corners of over-touristed regions abroad, the same possibility exists here at home. Canada has second cities, shoulder seasons, and hidden gems that reward curiosity without requiring a bidding war for beds.
Consider the Maritime provinces outside the brief summer surge. Think about Quebec’s Eastern Townships with its less well known (outside the province) culinary offering. Imagine the Okanagan or the Gulf Islands in late spring or fall, the Yukon in late summer, or the lesser-known corners of Ontario’s cottage country when the long weekends are over. These places offer the same natural beauty, cultural richness, and small-town hospitality that draw travellers to Canada’s icons, but with breathing room, better value, and the kind of authentic encounters that happen when tourism isn’t the only game in town.
There’s also opportunity in reframing what “Canadian travel” means. Rather than competing with the big operators for the same handful of bucket-list experiences, we could design trips that reflect the Wheel & Anchor ethos: slower pacing, local connections, community-building among members, and itineraries that prize depth over checklist destinations. A week based in a single Maritime village, exploring fishing harbours, artisan studios, and coastal trails. A rail journey through less-heralded landscapes or just at a quieter time of year. A culinary deep-dive into regional food traditions that visitors racing between national parks never have time to discover.
The appeal of staying closer to home has practical benefits too: no jet lag, no passport anxiety, no currency conversion, and for many a chance to discover parts of our own country that remain more idea than experience. There’s something quietly powerful about gathering a group of Canadian travellers to explore Canada together, turning familiar pride into lived knowledge.
So where does that leave us? The honest answer is: still working it out. Organizing Canadian travel requires a different playbook. One that leans into flexibility, creativity, and a willingness to go where the big operators don’t. It means scouting regions that haven’t yet been “discovered,” building relationships with local innkeepers and guides who can open doors that aren’t in the brochures, and timing trips to avoid both the peak-season crowds and the shoulder-season closures that can make logistics a puzzle.
It also means setting realistic expectations. A Canadian trip might not deliver the same exotic thrill as waking up in Morocco or Sicily, but it offers something else: a chance to see home through travellers’ eyes, to appreciate the extraordinary diversity within our borders, and to support the small businesses and communities that make regional Canada vibrant.
I’m not promising a full roster of Canadian programs tomorrow, but the idea is very much alive in my thinking. If we do it, we’ll do it the Wheel & Anchor way: thoughtfully designed, off the beaten track where it matters, and built around the community and connections that make any journey worthwhile.
In the meantime, if members have favourite corners of Canada they think we should explore—places that feel undiscovered, regions with strong local character, or “hidden-gem” (as much as I dislike the idiom) destinations that deserve more attention, I’m all ears. After all, the best itineraries often begin with a conversation and a shared curiosity about what’s possible.
The world may be our oyster, but sometimes the most rewarding pearls are the ones we find closest to home.
Gordon
P.S. I have to reiterate that I’m not making any promises that we can deliver on this idea anytime soon, but it is definitely worth the conversation.