PAX presents the 10 Most Fascinating Travel Advisors of 2026

Sales may win trophies, but fascination is what makes people lean in.

That’s the spark behind PAX’s “10 Most Fascinating Travel Advisors” list, our annual wink and nod to the industry’s most magnetic movers and shakers.

Now in its fourth year, the feature drops every Travel Advisor Day (the list, in case you were wondering, is inspired by the late Barbara Walters and her annual “10 Most Fascinating People” TV specials).

This year’s class? An impressive bunch of travel pros rewriting the rules with hustle and heart.

From sky-high ideas to sea-changing strategies to boots-on-the-ground brilliance, these advisors are turning the travel world on its head in the best possible way.

At PAX, we spend the entire year scouting our “Most Fascinating” picks. And while the travel industry is overflowing with deserving stars, there are always a few individuals — and dynamic duos — who stop us in our tracks.

So, in honour of Travel Advisor Day (and month), PAX proudly presents its 10 Most Fascinating Travel Advisors of 2026.

Christine Wilson (Envoyage) – The Pickleball Queen

Christine Wilson didn’t set out to become a pickleball-planning prodigy.

But somewhere between a Florida holiday and a cold Ontario winter with nowhere to play, she found herself at the centre of one of travel’s most unexpectedly joyful trends: vacations built around a paddle, a perforated ball, and a whole lot of camaraderie.

Wilson, an Envoyage travel advisor based in Owen Sound, ON, has been in the travel industry for 17 years. Cruises, Europe, all-inclusives—she’s done it all.

But it’s pickleball, of all things, that has given her career a second wind. Not a light breeze. A gust. The kind that carries 80 people to resorts and arenas with paddles and shared enthusiasm.

Her origin story is delightfully unassuming. While visiting Florida with her husband one winter, Wilson discovered pickleball, a sport often described as a mash-up of tennis, badminton, and ping-pong.

It hooked her instantly. Back home in Owen Sound, however, there was one problem: nowhere to play. So, she did what any resourceful person might do. She started a club.

Today, that club has more than 200 members.

That alone would be enough of a story. But Wilson didn’t stop there. A collaboration with the Taylored Pickleball Academy opened the door to something bigger: curated pickleball trips.

Her first excursion, about two and a half years ago, took a group to the Caribbean. It worked. Then it really worked. Soon she was running four to five trips a year, each drawing anywhere from 40 to 100 players of all abilities.

Not bad for a niche that didn’t exist in her original business plan.

“It’s opened up an entirely new client base, people who are active, social, and a genuine pleasure to work with,” Wilson says. “It’s also brought a more experience-driven focus to my business, leading to strong relationships, repeat clients, and new partnerships, including booking travel for one of the teams in the Canadian National Pickleball League.”

That experience-driven angle is key. These aren’t just holidays where people happen to play a bit of pickleball on the side. The sport is the backbone of the itinerary. Days are structured around clinics, games, and tournaments, balanced with enough downtime to remind everyone they are, in fact, on vacation. And the settings? Not exactly your local rec centre.

In Mexico’s Mayan Riviera, Wilson’s groups have played at the Grand Palladium, a resort she praises for its “incredible sports facilities,” where staff wait courtside with cold towels.

In Croatia, she organized a trip to Split that combined pickleball with a chartered ship.

Other destinations have included Italy, Costa Rica, the Dominican Republic, and Greece. There was even a voyage with Crystal Cruises from Manila to Seoul. The ship had an onboard court. “You can bet we were out there!” she says.

It’s slightly surreal, but that’s part of the appeal. Pickleball, for all its explosive growth, still carries a sense of novelty. It’s approachable, a little quirky, and above all, social.

“What really stands out is the community,” Wilson says. “People are welcoming and likeminded. You can show up almost anywhere and feel included.”

“That’s why it pairs so well with travel. It gives people a shared purpose, and it’s such an easy way to connect with others, whether you’re travelling with a group or meeting people along the way.”

That sense of belonging travels well. In fact, it might be the secret ingredient that makes Wilson’s trips so successful. Strangers arrive with paddles and leave with group chats, inside jokes, and plans to book the next trip together.

Of course, behind the scenes, it’s not all perfectly executed drop shots. Coordinating groups of up to 100 people is no small feat. Flights, accommodations, court bookings, skill-level matching. It’s a logistical puzzle that would make some advisors quietly back away. But Wilson leaned in.

“It’s strengthened my group travel expertise in a big way,” she says. “I’ve learned how to manage complex logistics, communicate clearly with large groups, and stay highly organized.”

It’s helped her focus on creating shared experiences for clients, whatever their passions may be. These days, Wilson has shifted slightly away from massive groups toward more personalized experiences for pickleball clubs, friends, couples, and families.

It’s a strategic move that allows her to focus on service without losing the magic that made her pickleball trips special in the first place.

Meanwhile, the sport itself shows no signs of slowing down in Canada. “Pickleball continues to grow at an incredible pace across Canada,” Wilson says. “Over the past year, I’ve seen a big increase in participation at all levels, more clubs, more organized play, and more people looking to improve through clinics and tournaments.”

Meanwhile, in Owen Sound, a state-of-the-art facility is now under construction, and Wilson’s husband has been hired as general manager. It’s fair to say the couple is all in.

Wilson didn’t just spot a trend. She built a community – and then figured out how to put it on a plane.

Louise Drouin (Voyage Louise Drouin) – The Mystery-Trip Maven

In an industry built on meticulously planned itineraries, Louise Drouin has built a reputation on something far more elusive: not knowing.

For more than 40 years in the travel business – today, she runs two agencies in Quebec: one in Drummondville, another in Sorel-Tracy – Drouin has perfected the art of the “surprise trip,” a high-end, high-trust experience where clients hand over thousands of dollars without the faintest clue where they’re going.

No Googling the hotel. No stalking departure boards. No pre-trip bragging rights about a Michelin-star restaurant. Just…mystery.

And that’s exactly the point.

Drouin started hosting surprise trips 16 years ago. Her first one? A 50-pax getaway to Provence, in southern France, at Club Med Opio to mark her 50th birthday (of course, none of her guests knew they were going there until they got there).

The guestlist? Loyal clients who, over time, had become close friends of Drouin through years of travelling with her – some of them having travelled with her more than 40 times.

They’re not exactly casual vacationers. These are seasoned, well-heeled, French-speaking explorers – primarily from Quebec, but also from Ontario and New Brunswick – who could book any luxury trip they want.

Instead, they choose to surrender control entirely.

“It’s kind of crazy,” Drouin admits. “This is not a $2,000 trip. My clients spend a lot of money, and they follow me around the world. I want to please them with something really special.”

So, she decided to flip the script.

“When you buy a trip, you have the program, you can go on the internet and look at the hotel. Whereas on mystery trips, all you have is the surprise. The good part is not knowing what you’re going to see.”

Again, these aren’t budget adventures. Drouin’s surprise trips can cost $16,000 to $17,000 per person – and that’s before flights in some cases.

And yet, they sell quickly. “Once I put one on sale, it's crazy at my office. It’s sold in a matter of hours.”

She goes to extraordinary lengths to guard the secret, designing each mystery trip herself, with almost no one in her offices (a team of nearly 30) privy to the itinerary.

“The worst part of a surprise is if people find out,” she says. “People have fun trying to guess.” 

But not just anyone can come along for the ride. Drouin curates her groups with the precision of a casting director.

There’s a questionnaire potential guests have to fill out, and in the end, Drouin is the one who accepts them or not.

It’s not about exclusivity, it’s about chemistry. The questionnaire asks about people’s abilities, where they’ve travelled in the past, their interest in ships, if they enjoy cold climates, hot climates.

“This way I know I’m travelling with people who want to be there,” she says.

What do travellers actually know before departure? Drouin may suggest what clothes to pack, but that’s where it ends. “They don’t know where they’re going,” she says.

From there, Drouin turns the entire journey into a kind of theatrical production. There are pre-trip parties, decoy clues, and just enough misdirection to keep even the most seasoned guessers off balance.

“I always try to trick them,” she says, delighted. “They’ll look at the flight schedule and try to guess where they're going.”

One particularly mischievous move? Hosting a cocktail reception at a Marriott airport hotel—letting guests believe they were about to depart—only to send them off to bed without a hint of where they’d be heading the next day.

For Drouin, it’s about staging moments. Even once guests arrive in destination, they still don’t know what’s ahead. They discover their itinerary each day, as it unfolds. 

Take a surprise trip to Dubai, for instance. “We had a private charter boat and we sailed in front of the Atlantis hotel,” Drouin explains. “I got everybody together to take a group picture, people remarked how beautiful the hotel was, and then I said, ‘Your luggage is already in your room. We’re staying there.’”

Cue collective “wows!” and disbelief.

Or the time she orchestrated an elaborate ruse involving a “tour guide” aboard a bus in Guatemala who was actually a ship captain. “He started talking about a beautiful Ponant ship being in town… and then surprised the group, telling everyone they were going on a Ponant cruise,” Drouin says.

During the pandemic, when outbound travel came to a near-halt, she surprised clients with a trip to Chibougamau, a lakeside town, way up in Northern Quebec.

She flew everyone in on Air Creebec, a Cree-owned regional airline. “That was one of my best ones. It was beautiful. Nobody had ever been there,” she says.

It’s part travel, part magic trick. And while surprise trips sound mildly anxiety-inducing, Drouin argues that’s exactly why it works. There’s no overplanning, no checklist. Just the present moment.

“One of my clients told me: ‘Louise, it's like being in front of a Christmas tree and you have a box to open, and you don't know what's going to be in the box.’”

That childlike anticipation is addictive. “When you don't know, you enjoy your day, day by day,” she says. “It has completely changed the way people travel.”

Of course, none of this works without trust. Deep, unwavering trust. “You have to trust the person behind the trip, for sure,” says Drouin, who now limits her surprise trips to roughly 20 guests

Fortunately, she’s spent decades earning exactly that. Her agency is intensely personal. “My travel business is from the heart. My customers know they can call me and I will answer the phone,” she says.

She hosts biannual brunches, personally welcoming hundreds of past clients at the door, where she shares her upcoming itineraries – traditional, non-surprise (but still very exotic) trips, created by her, spanning the globe, from Africa to river cruises to polar expeditions (her personal favourite).

She helped raise money for her tour guide partners around the world during the pandemic. She remembers faces, names and stories.

“You feel good when people trust you,” she says.

But Drouin, whose next surprise trip is scheduled for this September, is the first to admit her mystery adventures aren’t for the faint of heart – or the control-obsessed.

But for those willing to let go? “After people do a mystery trip, they say, ‘Wow. I miss it,’” she says.

That might be the most surprising part of all: in a world where travellers demand more information, more customization, and more certainty, Louise Drouin has built a thriving niche on the exact opposite.

Ken Houston (The Travel Agent Next Door) – The Cruise Critic

Ken Houston didn’t exactly plan to become a travel advisor.

And yet, from his home base in Bowmanville, ON, he’s quietly built a powerhouse cruise business – one that relies less on flashy marketing and more on something deceptively simple: answering people quickly, honestly, and often at odd hours.

It’s a method that sounds almost too simple. But then again, Houston is a man who has lived many lives, and has learned something essential from each one.

He started selling cruises in 2017, a few years before the pandemic hit. “I owned my own construction company at the time and quickly realized that, after doing it for 15 years, the two-by-fours and drywall weren't getting any lighter, and I wasn't getting any younger,” he says.

That construction company, he clarifies, was essentially a one-man operation. “I did basement renovations, I did it myself,” Houston explains.

The upside? Fast turnarounds and happy clients. The downside? It was physically demanding – and not exactly a long-term plan.

But Houston didn’t jump blindly into travel. Like many great pivots, this one started as a hobby.

His first cruise was in 1998 and then he started cruising more frequently with his family in 2011.

In those early years, he became an active poster on Cruise Critic, a popular online forum where cruise enthusiasts gather to swap tips, review ships, and share opinions.

He also mastered the art of finding his own deals, helping friends and family with their own cruise vacations.

“So, I thought, ‘Let’s try this?’” he says.

“Let’s try this” would eventually snowball into a business where roughly 80 per cent of his clients come from a single place: Cruise Critic, one of the world's largest online cruise communities.

It’s said to host more than two million registered members (and attract some 5.6 million monthly visitors).

To be clear: Houston didn’t join the site as a salesperson. In fact, that would’ve been against the website’s rules. “Like everybody on Cruise Critic, I was looking for information about what to expect on ships and from ports,” he says. “Then I started posting, and as I got more confident, I started posting more and more.”

What did he post? Everything. Dining advice. Cancellation policies. Wi-Fi packages. The kinds of questions first-time cruisers obsess over at 2 a.m. “People ask everything, and because I knew the answers, I’d post,” Houston says.

This is where things got interesting. During COVID, when the cruise industry was changing policies in real time, Houston became something of an unofficial expert.

“I eventually got to know Royal Caribbean’s policies better than Royal Caribbean did,” he says, only half-joking. “I helped guide a lot of people on Cruise Critic. They weren’t my clients, and I wasn’t asking them to be.”

That last part is key. Houston wasn’t selling. He was just helping. And people noticed.

“I think I have at least 50,000 posts on Cruise Critic. From there, people Google searched my name, and that’s how my business grew,” he says.

Today, 80 to 90 per cent of Houston’s clients are from the United States. Many have never met him in person, but feel like they know him anyway.

Because, in a sense, they do. “Online, you can talk to somebody for 10 years and get a sense of who they are,” Houston says. “They’re internet friends.” 

It’s not a client base, it’s a community. One that occasionally spills into real life, too, like the cruise Houston organized in 2023 that ballooned into a 60–70 cabin group of people who had mostly never met.

“Everybody got on board and we all had this sense of camaraderie, despite never meeting in person,” he says. “The friendships that developed from that cruise went beyond cruising.”

So, what’s the secret sauce? It’s not advertising. Houston barely does any. Instead, it’s speed. “It’s that sense of urgency that I bring to every booking,” he explains. “Clients can email me at six in the morning, or midnight, and I’m generally responding within five, ten minutes.”

Yes, even at midnight. “A lot of clients live in California and Texas, in different time zones. It’s eight, nine o’clock at night when they start doing their cruise planning when it’s midnight for me, but I’ll answer them,” Houston says.

This relentless responsiveness isn’t accidental. It’s inherited. Every job Houston has ever had demanded it.

From delivering pizzas in his college years for Domino’s, Pizza Pizza and Little Caesars  to becoming an area manager for Domino’s, to opening Blockbuster video stores in the 1990s during the chain’s expansion years (he opened Canada’s 35th store, as well as the first Blockbusters in Quebec), to becoming a regional manager for the Chapters bookstore chain, to teaching cabinet making and carpentry at Durham College to even managing office logistics for Elections Canada, his career has been a masterclass in urgency.

“I’ve never had a job where it’s, ‘If I don’t get it done today, I’ll get it done tomorrow,’” Houston says.

That mindset now defines his travel business and reassures clients who fear being left hanging while cruise prices fluctuate. “Me, answering that phone 24/7, is why clients trust me,” says Houston, pointing out that many of his clients are first-time users of travel agents. “I'm going to be able to get them that price drop.”

But Houston doesn’t try to be everything to everyone. He doesn’t book flights unless it’s business class. He avoids booking hotels. He sticks to what he knows best: cruises.

“I would rather focus on one thing, and do it well, rather than be a jack of all trades,” he says. It’s a philosophy that has paid off – earning him top rankings within The Travel Agent Next Door, particularly in Royal Caribbean sales, as well as a loyal, global client base.

Houston is now growing his business with Celebrity Cruises as his clients transition there, often as their children grow older, while maintaining loyalty status within Royal Caribbean family. His Viking sales are also up.

Looking back, Houston sees a throughline connecting all his careers, no matter how varied. “Everything was there for a reason,” he says. “It just fell into place, and I wouldn’t change anything about it.” 

Sometimes, the best journeys – whether in life or at sea – don’t always start with a map.

Jamsheed & Jennica Pocha (The Pelican Club) – The Insiders

If you thought luxury travel is just about butler service and private plunge pools, Jamsheed and Jennica Pocha would like a quiet word.

Preferably over a perfectly chilled glass of something you didn’t know existed, on a private island you didn’t know you could access.

As co-founders of The Pelican Club, a Toronto-based, members-only luxury travel and lifestyle management service, the husband-and-wife duo have turned their shared obsession with hospitality into something far more intriguing than a traditional travel agency.

Think less booking service, more global backstage pass.

Their story begins in Switzerland—specifically, at Ecole Hôtelière de Lausanne, where the pair met while studying hospitality management.

From there, their careers took on a suitably glamorous trajectory. Jennica, originally Swedish and raised in London, cut her teeth at some of Europe and the Caribbean’s most prestigious five-star hotels, including Claridge’s in London and Hotel de Russie in Rome.

Jamsheed, born in Bombay and raised in Toronto, spent nearly a decade immersed in the world of Four Seasons in London before branching into consulting, including work with EHL Advisory Services.

This duo didn’t just learn luxury. They lived it, refined it and took notes.

“The Pelican Club is a result of mine and Jennica's love of travel and obsession for luxury hotels,” says Jamsheed. “I am a self-proclaimed hotel nerd…I wanted to help others travel better, with a service level offered in five-star hotels throughout the planning process, the trip and after.”

That last part – before, during, and after – is where things start to get interesting. The Pochas spotted a gap. Not in destinations, but in depth.

“Luxury travel is a complex world of knowing who's who and where is best, what has been renovated and what is in need of TLC,” Jamsheed explains. “It's about understanding your client and being able to know what would suit them best.”

And perhaps more importantly, it’s about access. Real access. When they launched The Pelican Club, which serves clients worldwide, and part of Virtuoso, they deliberately sidestepped the traditional agency model in favour of something more intimate (and frankly, more demanding). Membership.

“We chose to have a membership model to build a loyal base of clients that we see as more than transactional one-off experiences,” he says. “We commit to them and they vice versa chose to work with our team as their support system for all things luxury, outside their home cities.

Translation: this is not for everyone. But that’s entirely the point.

“There are nuances and differences to what people believe luxury is to them,” says Jamsheed. “We vet who we work with and make sure that there is a right fit. We also don't limit our services to booking flights and hotels. We do it all, from the moment you leave your home till you return, we have every detail thought through.”

From spa treatments, to private guides, from access to top restaurants and tickets to be seen at the right events, the team builds trips and provides thorough itineraries through their own app.

Every itinerary is constructed from scratch, balancing personality, preferences, and a deep well of insider knowledge.

But what truly sets The Pelican Club apart isn’t just what they book – it’s how they make their members feel. “They have access to us and we care about them. We are in it together and help turn every rock,” Jamsheed explains.

It’s a deceptively simple philosophy, backed by a team that operates more like a tight-knit concierge unit than a traditional agency. Requests don’t politely stick to office hours, and neither do they.

“We expect to get after-hours and weekend requests and support each other to manage both our member needs and our own lives,” says Jamsheed.

On top of that, The Pelican Club gets clients into closed doors and makes sure they are treated like a VIP with upgrades “rather than rooms that have 'partial views.’”

“We are a booster pack to your EA or PA…you feel like an insider and not a tourist,” says Jamsheed.

That promise has led to some pretty over-the-top bookings: privatized islands, celebrity meet-ups, fully booked historical venues. Even a whirlwind, around-the-world journey completed in 30 days.

Yet for all the extravagance, the Pochas insist that modern luxury isn’t about excess, it’s about experience.

“Luxury is a very personal term,” says Jamsheed. “What we have seen is that our clients’ homes are now designed like, or better, than most luxury hotels. This means that a high-level product in hotels is now an expectation.”

“It brings service and experience to the forefront of what luxury is today. It's feeling a certain way in the Alps or doing something very unique in a beach destination.”

As for what keeps them inspired?

“We travel at minimum once a month, internationally,” says Jamsheed. “The world is huge and has many unexplored corners. It is filled with adventures and cultures that we continually want to indulge in.”

Just this year, in the first four months, they visited more than eight countries, from gorilla trekking in Rwanda, to the favelas of Brazil, to the mountains of Colombia, to relaxing with the family in the Caribbean to a work trip in Europe.

“We are very lucky to do what we love to, which is travel, and we get to help others do the same,” says Jamsheed.

Jan Poon (Postcard Vacations) – The Mama

In Canada’s travel industry, there are advisors, and then there’s “Mama Jan.”

Say the name out loud at a conference and you’re likely to get a knowing smile.

Calgary-based Jan Poon of Postcard Vacations didn’t set out to become anyone’s industry matriarch, but somewhere along the way, between decades of experience, steady guidance, and a knack for looking after people, the nickname stuck.

“I feel very touched and respected when fellow advisors and supplier partners call me ‘Mama Jan,’ even if it means they see me as a little seasoned and maybe really old,” says Poon. “It started years ago at a conference when a colleague, Shauna, began calling me that, and it simply stuck.”

It stuck so well, in fact, that one year her conference badge made it official.

“One year, I couldn’t find my name badge anywhere, only to discover it had been printed as ‘Mama Jan.’ I guess I’ve become everyone’s Mama and honestly I love it!” she says.

At 87, Poon has earned the title. Not just through longevity, but through a career that’s as layered as it is lively. She’s been in travel for 27 years, including 26 with Trevello, but her professional life hardly started there.

She became a travel advisor in 2000 after selling a retail business. “I was looking for a new and fulfilling career path. I wasn’t ready to retire,” she says. “What started as a fresh opportunity quickly grew into a passion and long-standing profession.”

Before travel, there was oil and gas, retail, and even a family restaurant business.

“I’ve always gravitated toward people-focused roles,” she says.

Born in Vancouver, she has been married to her husband for 67 years, and family remains at the centre of everything she does.

Today, that family spans generations—children, grandchildren, great-grandchildren—with around 30 people gathering around the table, and another on the way.

Long before travel, Poon was already a seasoned entrepreneur. For more than 35 years, she and her family ran a Chinese food booth at the Calgary Stampede—an experience she still recalls with vivid detail, right down to the pricing: $1.25 for a three-combination plate, with an egg roll for 50 cents.

It was hard work and fast-paced – an early glimpse into the energy that would later define her travel career.

Her business instincts didn’t stop there. Nearly four decades ago, she helped introduce a luxury Japanese skincare line to Canada alongside her sister-in-law—a venture that continues to this day.

If that sounds like the résumé of someone who knows how to handle just about anything, well, that’s because she does. Especially when travel plans don’t go quite as planned.

Take an incident in Tokyo. Working with a supplier partner, Poon once arranged an accessible transfer for a cruise client in Tokyo when it became clear that the vehicle that was booked wouldn’t meet the client’s need.

“The guide was able to arrange an ambulance that could properly assist. My client can now say she rode in a personal ambulance, touring Tokyo for six hours. It wasn’t what I planned, but served as a good reminder that even the best preparation can go sideways,” Poon says.

That calm-in-the-chaos energy is part of what’s made Poon such a beloved figure – not just to clients, but to colleagues.

And yes, to family, too. She’s the real-life mother of TTC Tour Brands’ Jodine Clement, a well-known name in the industry in her own right.

Their professional paths even once overlapped – the mother-daughter duo initially launched their travel business together before Clement later transitioned into sales roles.

Since then, Poon has built a thriving travel business with a particular love for cruising.

She’s earned her Master Cruise Counsellor designation and has booked everything from short sailings to world cruises. But ask her what really keeps her going, it’s not the destinations. It's earning her clients' trust. 

Poon also continues to work and connect with clients while living with Stage 4 lung and bone cancer, a diagnosis she received in 2019, with two years of remission. Despite this, her outlook remains forward-facing—much like the way she approaches travel and life alike.

“Mama Jan” isn’t just a nickname, it’s a role. The one who checks in on you, and somehow makes a big, fast-moving industry feel a little more human.

And if she occasionally calls herself the “Dinosaur of the Trevello family”? That’s just part of the charm.

In an industry that’s always chasing the next big thing, Mama Jan proves that experience, and a good sense of humour, never go out of style.

Karen Gill (Plan A Vacation) – The Sip, Sail & Swirl Specialist

Karen Gill doesn’t just sell travel. She pours it, swirls it, and pairs it with a perfect bite.

From her home base in Niagara-on-the-Lake, ON, the co-owner of Plan A Vacation has taken two Canadian passions – wine and travel—and blended them into something unexpectedly intoxicating: wine (and beer)-themed river cruises that don’t just visit Europe’s vineyards, but bring a taste of home along for the ride.

Like many, her career as a travel advisor started with a leap.

“26 years ago, I left the corporate world of Bell Canada and decided I could make money for myself,” Gill says. “I took all of that knowledge, jumped and grew.”

That jump eventually landed her in river cruising—but not before a few pivots. Destination weddings? Done. Pandemic reinvention? Check.

Today, she runs an 11-person team alongside her husband and agency co-owner, Steve, whose resume includes pioneering Niagara College’s teaching winery, brewing, distillery and cidery program.

Together, they’ve turned their shared love of food, wine and beer into a niche that feels both obvious and brilliant in hindsight.

“We're very passionate about it,” says Gill. “We decided to blend our two worlds and really show the world what Canadian wine and beer is all about.”

It all started on the Danube, where Gill experienced her first river cruise back in 2016 with Uniworld.

“I instantly found my jam,” she says, recalling that first sailing. “It was a vibe I really enjoyed. It was an emotional experience.”

She eventually brought her husband Steve on board a river ship, with a warning—one that would prove prophetic.

“I said to him, as he was walking on board, ‘Stop. Welcome to your new addiction.’”

The couple doubled down, eventually leaning into wine-themed cruises with AmaWaterways, who eventually sent their head sommelier, from California, to spend time with the Gills in Niagara.

“We toured around Niagara for two full days, showed him what we have, introduced him to wineries,” says Gill. “I had done wine-focused river cruises, but I wanted to take it to the next level.”

Enter: wine hosts. And not just any hosts. Some of Niagara’s finest. “We brought on Canada’s first wine host from Niagara,” Gill says. “They came on board and educated the entire ship.”

Passengers, while sailing through Europe’s most famous wine regions, learned about Ontario’s terroir, sipping Canadian favourites, discovering that yes, Canada does in fact make wine (and very good wine at that).

The concept goes well beyond a few tastings. The cruises are layered experiences—think truffle hunting, curated pairings on board, and lectures that connect Old World traditions with New World innovation.

“With our wine host, we help decide the pairings on board with the meals. The host also does lectures,” Gill explains. “The response was incredible.”

Another layer? Dinners on board AmaWaterways are partnerships with Chaîne des Rôtisseurs, one of the world’s oldest and largest international gastronomic society, and Karen’s husband, Steve, just happens to be a knighted member.

“We've bridged all of that together,” says Gill.

Sometimes, the guest list reads like a wine-world hall of fame.

“We did a cruise on the Nile in Egypt and brought Donald Ziraldo, who put ice wine on the world map,” Gill says. “He brought some of his rarest ice wines out of his personal cellar, we did an ice wine tasting and a lecture on the Nile.”

“He’s the Godfather of ice wine, and we were meeting the Gods of Egypt.”

Gill’s groups typically range from 30 to 60 people – small enough to keep things personal, often involving wine club members.

And, for exclusivity, Gill will plan pre- and post-cruise experiences, giving her guests access and bonding time with her hosts.

And yes, wineries play a role in filling the spots. “We bring all the marketing components, we’re co-branded with Ama and the winery. It gets promoted at winery events, people get excited about it.”

But wine isn’t the only thing on tap. In 2024, the Gills tested the waters with a beer-themed river cruise, partnering with Ontario’s Sawdust City Brewing. The result? Equal parts education and good times.

“We taught people how to pair beer with food. We brought a brew master. We did a wine versus beer experience…we got such incredible feedback,” says Gill.

Even a Danube flood during one cruise couldn’t dampen spirits. While “stuck” in Vienna, Gill found more craft breweries to keep her group engaged. At one point, they wound up at a local Oktoberfest.

“There were other people on the ship going, ‘Can we come with you?” she says.

At its core, Gill believes the pairing of river cruising with wine (and beer) is a natural one.

“People who enjoy river cruises generally enjoy good food and wine. It’s a great marriage,” she says.

As for what’s ahead? More cruises. More hosts. Canada has an official beer host, who’ll join a future cruise in 2027.

Has it elevated Gill’s business? “Big time,” she says. “It’s about working smarter, not harder.”

“We look forward to educating the world about what Canada has to offer. We’re proud to share that story.” 

Cheers to that.

Jessica Renshaw (Renshaw Travel) – The Holiday Healer

Jessica Renshaw has built a career helping people unsubscribe to burnout – one itinerary at a time. Based in Vancouver, she works at the intersection of luxury travel and something far less superficial: human wellbeing.

Think five-star resorts, yes, but also nervous system resets, grief processing, and the occasional Arctic cold plunge.

Renshaw didn’t arrive here by accident. She’s a third-generation steward of her family’s boutique luxury travel company, Renshaw Travel, founded in 1948 by her grandfather.

“I feel very proud to work with my family and carry on the legacy that my Grandfather started,” she says. “Running an independent travel agency is a bit like David versus Goliath as many travel agencies are getting gobbled up by giant corporations.”

She follows in the footsteps of her Grandpa and her Dad, who has been the owner of Renshaw Travel, a member of Virtuoso, for many decades now.

“My Grandfather loved to work and would hug everyone when he came into the office. I believe that is why he lived such a long healthy life,” she says. “My Father is also one with the business, he loves his work and it keeps him sharp as he is now in his 70s!”

Renshaw works alongside her mom and sister, who she joined in developing a wellness-focused brand: The Renshaw Wellness Collection. 

It highlights transformative travel experiences, top wellness resorts worldwide, and journeys designed with intention rather than impulse.

But at its core, the collection reflects a simple but powerful shift: travel isn’t just about where you go, but why you go there.

Renshaw’s approach is part strategist, part listener, part wellness detective.

“I specialize in listening to clients. It is my job to figure out where someone needs support in their life,” she says.

Her categories of wellness are surprisingly structured for someone whose work often involves emotional reinvention: active adventure, detox (physical, emotional and digital), wildlife & wilderness, rest & rejuvenation, and connection & culture.

Before travel entered the picture, Renshaw studied Kinesiology, earning an honours degree, and briefly worked as a certified personal trainer. That foundation still quietly shapes everything she does.

“Both my sister [who has two degrees in nutrition] and I were raised with health as a number one priority, so it certainly does impact how we assist our clients in designing their travel,” says Renshaw.

In her world, travel planning is not that different from personal training. You identify goals, understand limitations, and design something that actually works for the individual.

And over the years, Renshaw has seen travel do more than relax people. It has shifted life trajectories. Some clients arrive in crisis, others in transition, all in need of something they can’t quite name.

“Travel is wonderfully impactful to our compassion and empathy,” she says.

She recalls a client grieving the loss of her husband, who travelled to Africa for the first time and found something unexpectedly grounding in the experience.

Another client, recovering after a myocardial infarction, used travel as a catalyst to completely rethink his lifestyle for the sake of his young daughter.

These are not postcard moments. They’re turning points.

If there’s one misconception Renshaw is eager to dismantle, it’s the idea that wellness travel is solely about detox smoothies.

“It’s not just yoga and green juice,” she says.

Instead, it can look like silence, movement, wilderness, or even discomfort – if it leads somewhere better.

And for those who feel “stuck,” her first recommendation isn’t a meditation app. It’s a plane ticket.

“I think a trip is the quickest way to become unstuck from habituated patterns,” she says. “When you travel, you get out of your own way and begin to change the habit of being yourself.”

Nature plays a central role in Jessica’s philosophy – especially water. From warm seas to polar plunges, she sees it as both symbolic and medicinal.

“Any destination where you can go in the sea embodies this concept. In Hawaiian tradition, the vitamin “Sea” is the best medicine,” she says.

She’s also fond of extremes. “There is nothing like a dip in the Arctic or Antarctic waters to bring yourself to life!” she says.

At the heart of Jessica’s work is a belief that travel can interrupt patterns we didn’t even realize we were stuck in. Not by escaping life, but by re-entering it differently.

Or, as she frames it: “Giving yourself the time to figure out your truth and how to get back on the path towards loving your life.”

In other words, Renshaw designs the interruptions: intentional ones that happen to come with expert knowledge, and occasionally, an Arctic ocean dip for good measure.

Lesley Keyter (The Travel Lady Agency) – The Travel Lady

In Calgary, Lesley Keyter is something of a local celebrity – though not in the way you might expect.

She’s not an actor, pop star or politician, but say a few words in the checkout line at Safeway grocery store, and someone is bound to turn around and ask, “Where are you off to next?”

That’s because for the past three decades, Keyter has been a weekly fixture on Global TV, sharing travel advice with viewers as “The Travel Lady.” It’s a title that stuck and one she turned into a powerhouse brand.

But her path into travel? Completely accidental.

“I joined the travel industry shortly after I arrived in Canada – all quite by accident,” says Keyter, CEO and founder of South Travel Inc, better known as The Travel Lady Agency. “My profession up until then was in law, but when I came to Canada, I could not get a job despite having over 20 years experience, working for some of Johannesburg's top advocates.”

So, she pivoted. Hard. Spotting a newspaper ad for a travel franchise, she convinced her husband to take a leap with her. “I am good at sales I have to admit,” she adds.

What followed was less smooth transition, more trial by fire.

She recalls being in Vancouver at a franchise owners meeting. “I did not understand one word anybody was saying. GDS, OBD, code share, TMC and ‘flying behind the curtain.’ This was a new language.”

Undeterred, the couple opened a corporate travel office – despite having zero contacts. “What the hell were we thinking?” she says.

Their first marketing tactic? Fax machines, lots of them, and fax out a weekly newsletter.

“These computers were buzzing and hissing all day long and the response from people who were woken up by the fax in the middle of the night was epic!” she says.

Then came the lucky break that would change everything: television.

Her franchise had a deal with Global TV, and when a call went out for on-air talent, Keyter—despite being “too nervous to give a speech” back in her school days in Mbabane, Swaziland —stepped up.

“I knew I had to make it happen and the producer loved me!” she says.

That moment turned into a 30-year run. “I have seen anchors come and go. I think I am a bit of a fixture!”

The “Travel Lady” brand itself came about almost by accident too. While doing segments for the franchise, owners noticed clients asking for “that travel lady” from TV. When the franchise pulled out of the TV deal, Keyter made a bold move.

“The rep at Global said, ‘Well why don't you take it on?’ I said, "Are you kidding? We are only a small agency and this costs $1,000 a month.’ He countered: ‘Would you do it for $500 a month?’ I said, ‘You’ve got a deal.’ And I became The Travel Lady.’”

It was a gamble, but one that paid off in spades.

Travel, for Keyter, was always in her blood. Born in England and raised in South Africa, her childhood was shaped by movement.

“My father was in the Royal Navy and it seemed I was always the new kid in class from the top of Scotland to Malta in the Med,” she says.

Later, she explored Africa extensively – Mozambique, Swaziland, Zimbabwe, Seychelles, Comoros Islands and Madagascar – long before she ever sold a trip there.

Today, her agency specializes in custom vacations, higher-end cruising, and destinations like Africa, Europe, and Australia.

But selling travel in 2026 isn’t what it used to be – and Keyter has seen the shift firsthand.

“Way back in the day, the consumer really found it hard to book their own travel,” she says. “Now, there are numerous websites with flights, hotels, attractions and it can be difficult – especially doing custom travel, when you have someone price checking the individual components of the FIT you have put together.”

In other words: clients have more tools than ever. But not necessarily more clarity.

That’s one reason she’s skeptical of one of the industry’s biggest buzzword.

“Artificial intelligence has definitely made an impact, which I think is overrated,” she says. “It certainly can be useful, but we are seeing that AI can be extremely imaginative and cannot really be relied on. It is a guide, nothing more, and certainly does not meet the expertise of a qualified travel agent.”

For Keyter, expertise isn’t about algorithms. It’s about experience. And she’s had plenty of it.

Her favourite trip? “Antarctica by far,” she says, admitting that she never had a desire to go because she doesn’t like the cold.

But once she got there, “it was like being on another planet.” 

“Nature just overwhelms,” she says. “It was the profound silence broken only by the thunderous crash of glaciers of the sound of whales coming up to surface.”

Despite decades in the business, Keyter hasn’t lost her spark. If anything, she leans into the unpredictability.

“You never know what the day will hold. It is definitely a sexy industry,” she says. “We are not dealing with nuts and bolts. We are dealing with people's dreams, discoveries and ambitions.”

Of course, it’s not always glamorous. “Sked changes, cancellations, earthquakes and lost luggage” are part of the job. But that’s just background noise.

“They pale in the light of the joy of the sale and the satisfaction of the enthusiastic reviews you get when clients return from their trip,” she says.

Turns out, sometimes the best journeys aren’t planned. They’re improvised, a little chaotic, and just bold enough to work.

Carl Henderson (Tahiti By Carl) – The Tahiti Treat

It’s tempting to sell everything to everyone, but Toronto-based travel advisor Carl Henderson took a different route. He bet big on paradise – and won.

As a Certified Tahiti Specialist with Tahiti Tourisme and the face behind Tahiti By Carl, Henderson has built a thriving business focused almost entirely on one destination: French Polynesia. Yes, just one. And no, he doesn’t seem remotely bored of it.

Why did he become a travel advisor in the first place? “I wanted to do what I loved,” says Henderson, simply. “People told me I was crazy as travel agents back then made so little, but I didn't care.”

After earning a business degree in marketing, Henderson did what many dream of but few actually do—he went travelling. A lot.

Eventually, passion won out over practicality, and he entered the travel industry through a discount call centre at Virgin Holidays, before making stops at Carlson Wagonlit and later TPI (Travel Professionals International), now known as Trevello.

In 2005, he pressed pause on everything to travel the world and visit 35 countries. But the real plot twist came in 2003, on his first trip to Tahiti.

“I was travelling with Eric, my same-sex partner. It was my first trip ever with a same sex-partner. I remember how the locals totally didn't care that we were a gay couple,” Henderson says. “They were so warm and welcoming to us.  Right then, I fell in love with the people and culture.”

That emotional connection hit just as hard as Tahiti’s scenery, from the lagoons to the mountains.

“Every picture was jaw-droppingly beautiful and it was a luxury market I had never travelled and experienced before,” Henderson says.

Not bad for a trip he barely researched. “There was just some good agent rates and it seemed like a great place for our first trip together” he admits.

Sometimes, the best decisions are the least strategic. Back home, something clicked. Each Tahiti booking lit him up more than the last. “I realized the passion and excitement I had for those bookings,” he says.

“I also slowly started to learn that most consumers and agents didn't know a lot about the destination and some had very poorly-planned trips.”

By 2011, he decided to lean in and carve out a niche.

At first, he played it safe. “I didn't plan on only selling The Islands of Tahiti. I tried to get it up to about 50 per cent of my sales,” he says. “I worried about putting all my eggs in one basket.” 

Sensible, measured. The business-school way. Then the COVID-19 pandemic hit, which changed everything.

“I decided if the whole world could shut down, I would take a risk on one destination,” says Henderson.

That’s when Henderson went all in. While some paused, he rebuilt. He refined his niche, strengthened partnerships, and essentially became the Tahiti guy. When travel roared back, so did his business.

“Post-pandemic sales sky rocketed,” he says.

Now leading a tight-knit team of three, Henderson spends most of his time sending clients to a place he still visits usually twice a year.

“It’s not a big destination, but it’s spread out,” he says. “The resorts are continually upgrading and changing, so I feel to be the expert in the field, it is important to visit. Same for anyone on my team. It costs a lot, but the investment is worth it. Of course, I love going!”

His proudest booking? That’s a tough question, because there are just too many.

“We’ve had huge dollar volume bookings, month-long trips around the islands, helped with weddings, surprise engagements, celebrating triumph of beating cancer and other grand celebrations,” he says.

And then there are the extras – the experiences you can’t Google. “We’ve done private fire dances, romantic dinners on a remote island, fireworks for clients and so much more,” he says. 

Henderson will also dismantle misconceptions. Is Tahiti only for the ultra-rich? “Not true,” he says. “Most of our clients are hard-working middle-class travellers who save and want a trip of a lifetime.”

Also on the myth-busting list: Tahiti is not just for honeymooners, and no – you don’t need to mentally prepare for a 24-hour travel ordeal. (“It is only about eight hours from the west coast of North America,” Henderson says).

Still, while Tahiti dazzles, it’s the human side of travel planning that matters most.

“What I am most proud of is the relationship we build with our clients,” says Henderson.

These aren’t one-and-done bookings. Clients come back, send photos, join his YouTube broadcasts – and, in many cases, fall for Tahiti just as hard as he did.

For advisors flirting with the idea of niching down, Henderson doesn’t sugarcoat it: it takes time, money, solid supplier relationships and a bit of nerve.

“You must choose a niche that excites you…then dig into it 110 per cent,” he says. And don't restrict yourself to one neighbourhood, or even Canada, he adds.

“When you are an expert, clients don't care where you are located,” he says. “They just want to work with someone who specializes in the niche and can help them plan their best trip.” 

If Henderson’s story proves anything, it’s this: sometimes putting all your eggs in one basket isn’t risky. It’s exactly what sets you apart.

Sheena Revet & Heather Calvert (Marlin Travel – Regina & Moose Jaw) – The Storefront Storytellers

In an era when artificial intelligence can build an itinerary in seconds, two Saskatchewan-based travel entrepreneurs are proving there’s still enormous power in a real conversation across a desk.

Heather Calvert and Sheena Revet — the duo behind two thriving Marlin Travel storefronts in Regina and Moose Jaw — have built their business on something refreshingly old-school: human connection.

And they did it at perhaps the worst time imaginable.

“We opened our travel agency in the middle of the pandemic in September 2021,” Calvert says matter-of-factly, as if opening a bricks-and-mortar travel agency while global borders were snapping shut was perfectly reasonable behaviour.

It wasn’t, of course. But that’s partly what makes the duo so fascinating.

Together, Calvert and Revet bring more than 40 years of travel industry experience to the table. Calvert, who splits her time between Okotoks, Alberta and Regina, grew up travelling internationally after riding with the Calgary Stampede as a teen.

Revet, a Regina-based self-described “small town girl with a passion to see the world,” originally dreamed of working in event planning for the Calgary Stampede before discovering the travel industry could offer both logistics and global exploration.

Their paths crossed in 2010 while working together at Percy Hunt Travel, which, at one point, owned 23 Marlin Travel branches, which were sold in 2018.

Calvert focused on operations, training and accounting support, while Revet carved out a niche in group and incentive travel, producing Caribbean concert experiences with Canadian entertainers and organizing large-scale corporate trips.

“We always joked about being our own boss,” Calvert says.

Then COVID hit. For many travel pros, the pandemic was an extinction-level event. For Calvert and Revet, it became a catalyst.

“Why are we putting so much time in for someone else?” Calvert recalls asking. “We love this, we love working together. We love the business.”

What happened next sounds unbelievable in hindsight. While many agencies were downsizing or shuttering, clients kept calling them directly.

Upon bringing the Marlin Travel brand back to Saskatchewan, with the support of Transat Distribution Canada (TDC), one of their first major bookings involved a 500-person corporate incentive trip to Las Vegas – a complete with PCR testing logistics and constantly changing regulations.

Even Canadian country singer Johnny Reid came calling, lending his support, offering to do a river cruise collaboration.

Still: “We didn't know if we could make this work,” Calvert says.

Revet remembers her father’s reaction vividly. “He said to me, ‘You should probably upgrade your schooling and consider getting a government job when this is all done.’”

Instead, they signed a lease. By December 2021, fresh travel restrictions slammed the industry yet again. But they kept the doors open.

“Our door was unlocked,” Calvert says. “Clients came in saying, ‘Do we need an appointment? Do we need to wear a mask?’ We didn't have appointments. We were open regular hours.”

That accessibility became their superpower.

Today, their Regina branch operates six days a week, staying open until 8 p.m., with after-hours emergency support routed directly to the owners themselves.

In Moose Jaw, where they opened a second Marlin Travel in 2025, they doubled down on the same formula: local expertise, real people, actual office hours (and in a location that has housed a travel agency since the 1990s).

“If the phone rings, you get a person,” Revet says. “You don't get a voicemail.”

That matters deeply in Saskatchewan, where much of their clientele comes from farming, oil and potash communities spread across rural areas. Customers may drive two (or more) hours just to sit down with an advisor face-to-face.

And these aren’t necessarily modest bookings.

“The Saskatchewan farming community is quite affluent,” Revet explains. “When they walk in, they're going to have on their local hockey team t-shirt and their elevator grain cap, but they're buying a $135,000 Emerald yacht cruise.”

That Prairie pattern shapes how the pair approach travel planning. Their clients aren’t chasing flashy trends for Instagram. They want value, expertise and experiences worth remembering. “They want to be taken care of. They want everything planned for them from point A to point Z,” says Revet.

Ironically, artificial intelligence has actually helped fuel demand for their expertise.

“People now have a tool that they have to engage with to build what they think they want,” Revet says. “But there's a lot of error in what it's producing. It doesn't necessarily know the logistics of travelling.”

That’s where human experience comes in. The lived kind. Their nine-person team includes advisors who’ve lived overseas, hosted group tours and travelled extensively. “We don't just sell what's in a brochure,” Revet says.

And despite all the technological disruption, Calvert remains convinced the fundamentals haven’t changed.

“The internet's been here for 30 years,” she says. “Maybe we lost a few bookings to it, but it'll never replace the human touch.” That belief is now fuelling future expansion plans. “We're definitely looking at different books of business to grow,” says Revet.

“Older agency owners are reaching out to us to see if we want to expand. We like the brick and mortar model. It works here.”

For Calvert and Revet, the future of travel retail lies in an old-fashioned idea: building real communities around travel again.

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