On Location: “Keep On Pushing” – Envoyage Summit in Jamaica Unpacks Growth, Grit & Ambitions

What does it take to turn an impossible dream into reality?

Just ask Devon Harris, a retired military officer and founding member of Jamaica’s historic 1988 bobsled team (yes, the inspiration behind Disney’s 1993 movie Cool Runnings).

Harris, who grew up in Kingston, Jamaica’s capital, knows a thing or two about beating the odds.

He helped take Jamaica, a Caribbean country with no snow, no bobsled track and no winter sports experience, all the way to the 1988 Winter Olympics in Calgary, Alberta.

And while the team’s Olympic dreams famously came crashing down — quite literally, when their sled overturned during competition – Harris learned that failure doesn’t have to define success.

“The fact is, I did crash. It’s a part of my story, but it’s not the entire story,” Harris told a ballroom of Canadian and American travel advisors during a keynote address at Envoyage’s North American Summit in Jamaica last week.

Nearly four decades later, the three-time Olympian brought his signature “Keep On Pushing” philosophy to Envoyage’s North American Summit, held Oct. 20–24 at Princess Grand Jamaica, where travel advisors spent the week in workshops, breakout sessions and one-on-ones with suppliers.

Delivering an energetic, humorous and inspiring presentation, Harris connected his unlikely Olympic journey to today’s business challenges, from artificial intelligence to shifting consumer expectations.

He shared his “three Rs” for overcoming adversity: responsibility (own the moment), reframe (change the frame) and reset (win the next run). His mindset for taking action and recognizing opportunities where others see obstacles.

“Never ever confuse the unfamiliar with the impossible,” Harris told the room. “They are two completely different things.”

Big Opportunities

That spirit of resilience provided a fitting backdrop for Envoyage’s largest North American Summit yet.

Held in Green Island, a coastal community near Negril, the five-day gathering welcomed roughly 160 attendees for a packed program of learning, networking, and plenty of Jamaican hospitality.

The timing was meaningful. The event brought the travel industry back to Jamaica nearly one year after Hurricane Melissa, a devastating Category 5 storm that battered parts of the island.

For Envoyage, it was an opportunity to support a destination that remains a favourite among Canadian travellers while strengthening relationships across its growing network.

“It’s about bringing our community together,” Heather Baker, national marketing manager at Envoyage Canada, told Travel Market Report Canada, which was invited to cover the event on location. “Canada also loves Jamaica. It’s one of our top destinations.”

And there was no shortage of familiar Canadian industry faces.

Well-known reps from G Adventures, WestJet Vacations, Intrepid, Air Canada, ACV@Home, Transat, TTC Tour Brands – to name a few – were on hand to huddle with advisors and participate in a trade show.

Two Powerhouses Join Forces

But this year’s Summit marked a particularly important chapter in Envoyage’s evolution.

One of the biggest talking points in Jamaica was Envoyage’s new partnership with Travel Leaders Network (TLN), the first consortium partnership in the host agency network’s history.

Announced in July, the alliance made its big debut at the Summit, giving advisors a closer look at the additional resources now available to help grow their businesses.

For Baker, the partnership represents a significant expansion of an already substantial support system.

“It’s two superpowers coming together,” she said, referring to Envoyage’s backing by Flight Centre Travel Group (FCTG) and TLN’s extensive North American network.

Mike Migliore, TLN’s senior director of sales, was on site, walking advisors through the consortium’s supplier relationships, tech and business-building tools.

Among the offerings highlighted were Cruise Complete, TLN’s cruise booking platform; Agent Profiler, a lead-generation tool designed to connect advisors with potential clients; social media resources; luxury travel products; and preferred supplier programs.

“It’s about giving advisors more options and tools to build their business,” Baker said, adding that the partnership has been well received.

Envoyage Finds Its Footing

The link with TLN comes as Envoyage continues to carve out its place on the global stage, making a name for itself in the competitive host agency space.

Launched in early 2024, Envoyage replaced the long-running Independent by Flight Centre brand as part of a gradual international rollout, beginning in the United States before arriving in Canada.

Previously, Australia-based FCTG operated separate independent agency brands across its international markets.

Envoyage brought those businesses together under one global banner, creating a connected ecosystem of products, technology and services, including platforms like Travefy.

The strategy? Think global, act local. Tap into the resources and best practices of a worldwide organization without losing the personal relationships, local expertise and entrepreneurial spirit that independent advisors bring to the table.

And it’s got some serious reach. Today, the network connects approximately 2,500 travel professionals worldwide.

Asked whether Envoyage has found its footing since its launch, Baker said the brand has been well received by advisors and supplier partners, with recognition continuing to grow.

“It’s an incredible community where people have have poured so much into building their travel businesses,” she said.

That evolution is also reflected in its international conference strategy.

Envoyage’s “Worldwide” event brings together advisors from Canada, the United States, South Africa, Australia and New Zealand. Last year’s edition was held in Sun City, South Africa, with the next global event scheduled for September 2027.

Meanwhile, the Canadian network continues to expand, supported by new leadership appointments this year, including Joe Scardigno as national sales director and Jessica Smid as business development manager.

“The future is limitless,” Baker said.

AI, Luxury & the Next Great Wealth Transfer

There was plenty of serious business on the Summit agenda.

General sessions, including advisor fireside chats, explored some of the biggest opportunities and challenges facing the travel trade.

Among the most thought-provoking discussions was a forecast by Christina Pedroni, executive vice-president and general manager of Envoyage USA that presented trends that are expected to reshape the advisor business in the years ahead.

Artificial intelligence was a recurring theme, with conversations examining how technology is changing the way consumers research and book travel, and why advisors need to adapt rather than compete with automated tools.

That message echoed Harris’s keynote, in which he encouraged advisors to see AI as an opportunity to strengthen their value.

“Instead of asking what is AI taking away from us, you should be asking what becomes more valuable because AI exists,” Harris said.

Another takeaway was the growing importance of value over price, the benefits of selling group travel, introducing service fees, and preparing for two major demographic shifts: a wave of retirements and the coming great wealth transfer.

Canadians Are Still Travelling. Just Differently.

The changing habits of Canadian travellers were another important topic.

Baker acknowledged that geopolitical tensions and rising travel costs are influencing where Canadians choose to vacation, but emphasized that demand for travel remains strong.

Rather than abandoning international travel, some Canadians are reconsidering destinations (like the United States) and looking for alternatives (like Portgual) that better suit their priorities.

Envoyage is also seeing bookings rise in Japan, Southeast Asia and the South Pacific.

At the same time, higher costs, brought on by rising jet fuel prices, are prompting travellers to think more carefully about where they spend their dollar.

That, Baker suggested, reinforces the importance of working with a travel advisor who understands a client’s priorities.

“[Consumers] are leaning into working with a trusted travel advisor to get the most benefit from the dollars they’re spending,” she said.

Two Journeys, One Community

For Wendy MacCrimmon, founder of wMac Travel, success in travel isn’t about selling everything to everyone. It’s about finding your niche and embracing what you love.

The Ontario-based travel advisor, who specializes in global women’s adventure retreats and small-group trips, was invited to share her entrepreneurial journey on stage at Envoyage’s Summit.

An award-winning professional photographer who lives on a deer farm north of Muskoka, MacCrimmon entered the industry just two years ago.

After initially selling independent travel and all-inclusive vacations, she decided to focus exclusively on her passion: taking women on adventures to destinations they might hesitate to visit alone.

Her intimate groups typically include 10 to 14 travellers, with itineraries built around hiking, photography, nature, wildlife and food. Destinations have included Tanzania, Zanzibar and Uganda, with future trips planned for Patagonia, Italy and Scotland.

Photography is signature element. MacCrimmon personally documents each journey, providing participants with a collection of professional images.

“I think that there’s something really special about women getting together with each other. They can just be themselves, let loose, laugh, and have a good time. Everybody supports each other,” she told Travel Market Report Canada.

Attending her second Envoyage conference, MacCrimmon said learning from fellow advisors were major highlights.

“Sitting at a desk by myself is not the same as coming here and hearing everybody else’s experience,” she said.

Supplier conversations, particularly around travel insurance, also provided valuable insights.

For now, MacCrimmon is happy organizing five trips annually, although she sees potential to double that number.

She credits Envoyage’s supportive environment for helping her grow.

“It’s an amazing, supportive community,” she said.

For Joanne Roberts, a Halifax-based travel advisor with three decades of industry experience, the Summit was an opportunity to celebrate professional achievements and explore new ways to grow her business.

Attending her third Envoyage conference, Roberts was recognized as Canada’s top ocean cruise seller and top river cruise seller, two honours that reinforced her plans to focus more heavily on luxury cruising, river voyages and expedition travel.

Roberts first entered the travel industry 30 years ago, having previously worked for an airline.

After taking 15 years away to raise her children, she returned as an independent travel advisor with what was then Independent by Flight Centre.

“I thought I’d never get a customer. Ever,” she recalled.

Fifteen years later, Roberts has built a client base of approximately 3,000 travellers, many of whom are repeat customers booking three or four trips annually.

She also earned a place on Envoyage’s prestigious Icons list of top-selling advisors last year, a goal she had been working toward for several years.

Despite her extensive experience, Roberts said attending industry conferences continues to provide valuable business-building opportunities.

“I’ve learned something every hour here,” she told TMR Canada.

She said the greatest value of belonging to Envoyage is the community itself.

“It’s my family. It’s the agents that I connect with the most,” she said.

Giving Back in Green Island

One of the Summit’s most memorable moments took place beyond the resort, as attendees traded conference rooms for classrooms, paintbrushes and plenty of smiles.

During Envoyage’s Give Back Day, travel advisors and supplier partners visited Green Island Primary School, which serves approximately 500 students.

Attendees spent the morning painting benches, reading with children and sharing stories about life in Canada and the United States. School supplies were also donated.

The highlight? An impromptu dance party in the school parking lot, where students and visitors came together for music, laughter and plenty of moves.

The experience offered a meaningful connection with the local community and a reminder that travel’s impact extends far beyond resort gates.

Reggae and Cliff Jumping

The Summit also delivered a taste of Jamaican culture, courtesy of a Jamaica Tourist Board-hosted dinner at Negril’s legendary Rick’s Café.

Established in 1974, the cliffside hotspot is famous for its spectacular sunsets, live reggae, Caribbean cuisine and daring cliff jumpers.

Advisors and supplier partners enjoyed jerk chicken, seafood and cocktails overlooking the Caribbean Sea, with music and cliffside thrills adding to the atmosphere.

The Summit concluded with glamorous gala at the Princess Grand, where the winners of a points-based competition were revealed.

Throughout the week, advisors earned points by connecting with supplier partners and completing a series of challenges, adding a little friendly competition to the agenda.

More Than Just a Conference

For independent advisors accustomed to running their businesses solo from home, the Summit was a reminder that sometimes the best connections happen when you close the laptop and get in the same room.

As Baker put it, “Envoyage events are an investment in their business.”

“They walk away with actual items they can put to work right away.

And attendees had plenty to take home. Harris, who helped turn one of the most unlikely ideas in sporting history into an Olympic reality, perhaps summed it up best.

“Inspiration alone doesn’t grow a business,” he said. “A conference doesn’t grow a business. It’s the decisions that you make.”

For Envoyage advisors heading home from Jamaica, the next run is theirs to win.

And the winners are…

Envoyage Canada announced its top-performing and most engaged travel advisors at the Summit. See the winners’ list here!

Top Insurance Sales – John Castell

Top Ticket Sales – Julie Smigadis

Top River Cruise Sales – Joanne Roberts

Top Ocean Cruise Sales – Joanne Roberts 

Top ITC Bookings (excluding groups) Kirsty Roberts

Top ITC Bookings (including groups) Janice Bell

Top Team Sales – Travel Our World 

Top Individual Sales within a Team – Becky Madsen (Travel our World)

Top Individual Advisor Sales – John Castell 

Outstanding Business Ownership – Alana Halford Bowles, Your Vacation Guru

Envoyage Rising Star – Alex Chan

Envoyage Luminary Award – Wendy MacCrimmon

Myrtle Gordon Education Award – Paula Perez

Kristin Anderson Community Award – Lynda Tomilin