Roundup: Prince of Travel Signature Event Toronto 2025

After months of anticipation, the Prince of Travel Signature Event Toronto 2025, presented by All-Inclusive by Marriott Bonvoy, came to life this past weekend at the ever-stylish W Toronto.

With over 150 people in attendance, this was our largest and most dynamic Signature Event yet. It encompassed a full day of learning, connection, and celebration with the travellers, professionals, and enthusiasts who make up the Prince of Travel community.

Welcome to the Event

Registration began at 9:00am in the Promenade on the sixth floor. Guests checked in, received their name badges and swag, and chatted over morning coffee before taking their seats in the ballroom.

Prince of Travel Platinum Members received a Prince of Travel hoodie as well as double entries into the prize sweepstakes (more on this at the end).

Our emcee, Kajal, opened the day with a warm welcome and preview of what was to come.

She set the tone for an engaging, insight-packed program and reflected on the growing strength of the Prince of Travel community: a group of travellers united by curiosity, generosity, and the shared goal of turning points into life-changing experiences.

Kajal then invited Peter, our Managing Director, to the stage to introduce the Prince of Travel team. 

Unlike our past Signature Events, this one was more jam-packed with information than ever before, with so many dynamic session topics filling up an entire day.

Air Canada’s Spin-to-Win Trivia: A Highlight From the Moment Doors Opened

This year, we were also thrilled to welcome Air Canada as an onsite sponsor – and they brought an energy that was felt from the moment guests stepped in.

During registration, attendees were greeted with an eye-catching Aeroplan spin-the-wheel activation, where everyone had the chance to win Aeroplan points by spinning the wheel and answering a trivia question about Air Canada.

The questions ranged from fun true and false prompts to more challenging queries – including one that stumped more than a few people:

“How much do you need to spend on a premium Aeroplan credit card next year to earn 10,000 SQCs?”

The best part was watching members subtly (and sometimes not-so-subtly) help each other answer. It was competitive, collaborative, and very on-brand for our community.

The activation continued into the morning coffee break and drew a steady crowd, thanks to some very generous prizes – including giveaways as high as 4,400 Aeroplan points.

We deeply appreciate Air Canada for not only sponsoring the event, but for creating such a fun and memorable experience for our attendees.

With energy already high from the trivia and morning conversations, we shifted into the first theme of the day: Cracking the Aeroplan Code – a deep dive into Air Canada’s loyalty ecosystem.

Cracking the Aeroplan Code

Peter and Chris opened with an inside look at Air Canada’s upcoming 2026 Elite Qualification changes, explaining what’s changing and how travellers can adapt. Their insights helped attendees understand how to navigate the evolving status landscape and get the most from every mile flown.

Next came a lively team panel hosted by Kajal, featuring Amy, Sarah, and Chris. Each shared a unique perspective: Amy spoke about balancing family travel with mid-tier status, Sarah offered insight as an Air Canada Super Elite, and Chris shared how he uses points to book premium cabins and creative itineraries.

To round out the segment, Steve and Zach took the stage for a detailed session on maximizing Aeroplan redemptions. They walked the audience through practical examples of complex itineraries, stopovers, and partner bookings, showing just how far a single redemption can go.

Morning Break

Guests stepped out into the Promenade for the morning break, with refreshments sponsored by Autograph Collection.

Over coffee, tea, and pastries, attendees caught up with one another and shared their favourite takeaways from the morning session. I particularly enjoyed catching up with many of our Platinum Members, as this is the first time we’ve met face to face.

Inside Our Wallets & the Cross-Border Playbook

Back in the ballroom, Kajal welcomed everyone to Inside Our Wallets, a candid team panel that explored the different ways our team members build and optimize their credit card portfolios.

Jason, Zach, and Amy compared approaches ranging from minimalist to maximizer to family-oriented setups.

The discussion underscored that there’s no single “best” strategy, only the one that fits your lifestyle, spending habits, and travel goals. Particularly, the highlights were the American Express^® Cobalt^® Card as well as the RBC® ION+™ Visa^‡ Card.

Following that, Rashaad and Rachel led The Cross-Border Playbook, a detailed walkthrough of how Canadians can tap into the lucrative U.S. credit card ecosystem.

They shared practical steps for getting started with Amex US, ITINs, and moving into more advanced maneuvers with Chase, Citi, and Capital One.

The session concluded with a lively Q&A that spilled naturally into the lunch hour – a testament to just how many attendees were inspired to expand their earning potential beyond Canada’s borders.

Lunch

At 12:45pm, attendees enjoyed lunch hosted by All-Inclusive by Marriott Bonvoy in the Promenade and Atrium spaces.

Over a well-received buffet (there was no food left over), conversations flowed freely from Aeroplan sweet spots to how to score the best suite upgrades, and everything in between.

The atmosphere captured what makes these gatherings so special: a shared enthusiasm for travel that turns strangers into friends within minutes.

Our industry partners such as Nora Dunn, The Professional Hobo, and Spencer and Ashley proved to be popular at lunch tables.

Winning in a Shifting Game

The afternoon began with Winning in a Shifting Game, a session devoted to navigating the ever-changing world of loyalty programs.

Jason and Steve opened with a look at fixed-value points programs, showing how currencies like Scene+ and CIBC Aventura can deliver steady, practical value for positioning flights, car rentals, boutique hotels, and everything else outside of premium flights.

Next, Amy and Nancy presented Hotels: Points vs. Cash, exploring how to decide between redeeming points, paying cash with hotel direct bookings, or booking through Prince Collection, our in-house luxury travel agency. 

They compared real-world examples where it makes sense to redeem points as well as when agency-exclusive perks such as upgrades, breakfast, and resort credits tipped the scales in favour of cash stays, especially for those seeking elevated experiences.

Finally, a short audience Q&A was held with Amy, Rachel, Chris, and Steve, who discussed how their personal travel tactics have evolved in 2025. Topics ranged from award search platforms and flight-release patterns to new U.S. program partnerships that open up broader opportunities for Canadians.

Afternoon Break

Guests took a well-earned pause for the afternoon break, with refreshments sponsored by W Hotels.

Over Marriott cookies and other small bites, the conversation shifted from redemptions to travel memories. It was so nice to see familiar faces from our events dating back to Vancouver Signature Event 2021 as well as new faces who were just beginning their Miles & Points journey.

The buzz of connection and community continued right up until the final sessions of the day.

From Economy to Extraordinary

The last theme of the day, From Economy to Extraordinary, highlighted how travellers at any stage can unlock elevated experiences through strategy and creativity.

Rachel and Chris opened the session with an inspiring look at premium cabin redemptions, walking attendees through sweet spots and advanced booking tools that make aspirational travel attainable – from Singapore Suites to ANA First Class.

Then Zach and Steve explored Flavours of Avios, guiding the audience through the web of British Airways, Qatar, and Finnair Avios and showing advanced tactics on positioning your Avios to unlock exceptional experiences.

To conclude, Jason and Rachel brought things full circle with practical advice on making the most of economy travel: when to redeem, when to pay cash, and how to use upgrades, seat selection, and timing to stretch comfort and value even further.

Closing Remarks & Prize Draws

As the afternoon drew to a close, Kajal returned to the stage to share final reflections and thank everyone for being part of the day. She expressed gratitude to our sponsors – All-Inclusive by Marriott Bonvoy, Air Canada, W Hotels, Autograph Collection, and Chexy – as well as the speakers and attendees who made the event such a success.

Kajal then invited Peter back to the stage to host the Prize Draw, which featured some truly exciting rewards:

• A W Punta Cana All-Inclusive stay with airfare, courtesy of Marriott Bonvoy
• A night at W Toronto in the Penthouse II Suite
• A night at St. Regis Toronto in Superior 1-Bedroom Suite, including breakfast
• A night at Ritz-Carlton Toronto, including breakfast
• A $250 Prince Collection hotel credit
• 6 months of fee-free transactions from Chexy

A fun note that every prize was won by a Prince of Travel Platinum Member or Concierge client, highlighting that double entries do make a big difference in the prize draw.

If you’ve been thinking about diving deeper into the world of miles and points, or simply want to connect with fellow travellers who share the same passion, now is the perfect time to join.

Our Black Friday promotion gives you 25% off an annual Platinum Membership, and as a member, you’ll get first access to future events, plus higher chances of winning exclusive giveaways.

VIP Experience

For a select group of guests, the celebrations continued with an elevated VIP Experience that embodied the spirit of discerning travel.

Hosted over W Toronto’s signature afternoon tea, The Discerning Traveller Roundtable brought together entrepreneurs, executives, and seasoned globetrotters for a curated conversation about travel as both craft and lifestyle. Participants exchanged ideas on how to turn time, points, and spend into exceptional journeys and lasting memories.

The evening progressed to post-event cocktails in the W Toronto Penthouse Suite, where VIP guests connected with our Founder, Ricky Zhang, in an intimate setting before the highlight of the night: the Caviar & Champagne Mastermind Dinner at TONO by Akira Back.

This indulgent dinner offered a world-class tasting menu worthy of Ricky’s top First Class flights. It was the perfect finale to an unforgettable day of connection and inspiration.

Conclusion

The Prince of Travel Signature Event Toronto 2025 was a milestone for our growing community – our largest, most comprehensive, and most inspiring event yet.

From deep-dive presentations on Aeroplan and cross-border points strategy to afternoon discussions on adapting to a shifting loyalty landscape, every session reflected the shared curiosity and passion that define Prince of Travel.

To everyone who joined us, supported us, and helped make this day possible – thank you.

We can’t wait to see you at the next Signature Event.