Travel advisors share insights on the new luxury and crafting transformative experiences for clients
Can you tell us a little about yourself and what you specialize in?
JG: I’m the sr. travel concierge and founder of Passport to Passage, based in southwestern Ontario. I’m a certified travel counsellor with over 16 years in this industry. I lead a team of six, but I’m backed by a wide network of colleagues who generously share their collected wisdom when called on.
I don’t think of this business as booking vacations – we craft journeys. My specialty is curated expedition travel and expert-led luxury experiences: the trip you take when you’re at an inflection point and need to be changed by what you see. My clients are people at a crossroads – retired, empty nesting, or just realizing they need to be shaken awake by something extraordinary. I prefer to keep the groups small and build the journey around the client’s story, not pulled off a shelf. I came up through weddings and large groups. In fact, I had an underwater scuba wedding myself, so I’ve always believed that the most meaningful moments deserve an extraordinary setting.
Of course, none of this would be possible without my host agency The Travel Agent Next Door. They provide the training, the supplier relationships, and the access to the luxury products I need to make these passages happen. I design the journey; they give me the road to build it on.
DW: My name is Darlene Wipp, and I am entering my 36th year in the travel industry. I began my career as a travel agent in 1991, drawn by my lifelong love of travel and the opportunity to help others discover the world.
I started as a leisure travel agent before moving into corporate travel, where I spent nearly 20 years. During that time, I was invited to help manage incentive travel programs, an experience that ultimately shaped the next chapter of my career. It led me to specialize in incentive and small-group travel, with a particular focus on luxury experiences.
What I love most about travel is the opportunity to see the world while truly immersing myself in its people, cultures, and traditions. Every destination offers something new to discover, and I feel incredibly fortunate to have built a career that allows me to share that experience with others. After more than three decades in the industry, my passion for travel remains as strong as ever.
In your experience, how has the definition of luxury travel changed over the past few years?
JG: Luxury used to be about thread count and butler service. Now it’s about access and transformation. My clients already have nice things – what they don’t have is a once-in-a-lifetime wildlife encounter they’ll still be talking about when they are 80. Maybe a private jet across Africa, or a business coach unpacking their next chapter while sailing the Mediterranean. These are the kinds of journeys I curate for them. The new luxury is irreplaceable experiences. It’s not about being surrounded by the finest of everything; it’s about coming home a different person than when you left. That shift from amenities to meaning, is what stands out the most from my perspective.
DW: Luxury travel used to mean private jets and expensive resorts whereas nowadays it leans towards the simple luxuries of life. Holistic healing, connection, authentic experiences, good food. Modern luxury is overall wellness.
What are the biggest luxury travel trends you’re seeing?
JG: The biggest trend I’m seeing is expert-led group travel. People want to go deep, not just far. They want a photographer on their wildlife expedition, a coach on their cruise, a conservationist on their safari – someone who elevates the experience from a trip into a genuine experience. And they want a small, more intimate setting.
I’m also seeing clients go further – Japan is hot right now, and expedition cruising is having a real moment. People who’ve been everywhere are looking for somewhere that still feels like a discovery. The other thing that stands out is how far out clients are booking. I have group bookings locked in for two or more years from now. These are bucket-list trips, and my clients are saving for them – sometimes a year or more – because they understand that an irreplaceable experience is worth more than another week at a familiar resort. The ‘why’ is driving the ‘where’ more than ever before, and the ‘when’ is getting further out.
DW: Today’s clients are seeking more highly customized itineraries, placing greater value on authenticity, meaningful connections, and unique experiences rather than traditional, predictable travel.
From curated private tours to highly personalized journeys, travellers are looking for experiences that reflect their individual interests, passions, and lifestyles. In the luxury market especially, clients are moving beyond conventional indulgence and seeking deeper, more restorative experiences. Wellness, rejuvenation, and holistic health are increasingly becoming integral elements of luxury travel, with travellers looking to return home not only refreshed, but genuinely transformed.
What’s the biggest misconception about luxury travel?
JG: I think advisors are wondering where to find the luxury client. The truth is that any one of their clients can be their next ‘luxury client.’ The misconception is that luxury is just for the rich. It’s for the committed. It’s about prioritizing the once-in-a-lifetime over the five-star familiar. Some clients plan out a year or more and save up to do one extraordinary journey, and it means everything to them. Luxury isn’t a price point – it’s a decision about what matters enough to invest in.
DW: The biggest misconception about luxury travel is that it is simply about high spending and opulent hotels. Most people consider it to be something only attainable by the ultra-wealthy. In contradiction, it is more about exceptional experiences, unforgettable memories and valuing time spent over money lost.
What’s the most a client has ever spent on a luxury escape and what did it entail? Or, if you prefer, that’s the price range of your average luxury bookings?
JG: I tend to frame this in ranges, since every journey is so different. At the top end, I can curate experiences through partners that offer private jet expeditions that run 22 to 26 days and can cost $100,000-plus per person. These are continent-hopping adventures that most people will only do once in a lifetime. At the other end, I’m offering wildlife expeditions that come in well under five figures – and to me those are just as much a luxury experience as the six-figure jet journey. My average booking is climbing because I’m attracting clients who see travel as an investment, not an indulgence. The price tag doesn’t define the luxury – the intention behind it does.
DW: It really depends on the destination, length of stay, travel preferences (upgraded flights/ private tours, etc.) and, most importantly, what the experience entails. That said, my clients currently invest an average of $30,000+ per trip, with my highest-value personal travel reservation to date coming in at just over $90,000.
At that level, it’s less about simply booking a beautiful trip and more about creating a truly exceptional experience, one that is entirely tailored to the client, from the destination and accommodations to the access, experiences, and details that make the journey feel completely effortless and unforgettable.
What’s one upgrade that’s always worth recommending?
JG: The expert. The private guide. The embedded coach. The person who turns a trip into a real adventure. You can upgrade your suite, your flight, your transfer – and all of those are nice. But the upgrade that actually changes the experience is the human one. The same ‘vacation’ changes the perspective when you have a marine biologist swimming beside you explaining what the whales are doing, or a photographer teaching you to see light differently, the trip stops being something you consumed and becomes something you learned from. That’s the upgrade I always push for.
DW: For long-haul travel, I almost always recommend upgrading your flight to at least Premium Economy, or higher, depending on the journey. The difference in comfort can transform the entire travel experience, particularly on an overnight or ultra-long-haul flight. More space, better service, and the ability to arrive feeling genuinely rested can be well worth the investment, especially when the rest of the trip is designed around luxury and ease.
When it comes to resorts, room selection is entirely personal, but I always recommend requesting a specific room type or location whenever possible. Those small details can make a surprisingly big difference in how you experience a property. For example, I typically request a room away from the elevators, as hallway traffic and noise can easily disrupt an otherwise peaceful stay. It’s a simple request, but one that can make your time at the resort that much more enjoyable.
What’s your favourite luxury property or cruise line you’ve personally experienced and why?
JG: La Maison Arabe in Marrakech. It’s Morocco’s first boutique Riad-hotel, tucked into the Medina, and it has this extraordinary history. Winston Churchill used to dine there, along with Hemingway and Jackie Kennedy. I stayed there at the end of a G Adventures trip through Spain, Portugal, and Morocco, and we booked the Royal Suite, which is a three-level duplex: a salon with a fireplace on the ground floor, a bedroom and marble bathroom above, and your own private rooftop garden with a soaker tub overlooking the medina. The service we experienced was unbelievable – the kind where they anticipate what you need before you know you need it. What I love about it is that it’s not a polished international chain – it’s a Riad, a traditional Moroccan house built around a courtyard, with 37 rooms and a soul you can feel. That’s my kind of luxury: intimate, storied, and impossible to ever forget.
DW: One of my favourite luxury stays has been at Beau-Rivage Palace in Lausanne, Switzerland. Set directly on the shores of Lake Geneva, the hotel combines an extraordinary setting with spectacular views, Michelin-starred dining, and impeccable service.
What truly stood out to me was how effortlessly everything came together. From the beauty of the property and its surroundings to the attention to detail and warmth of the service, it was an experience that felt genuinely special. After nearly four decades of travelling, it remains one of the most incredible hotel stays I’ve had and one I would happily return to.
I was also fortunate enough to sail aboard the QE2 before she was retired as a Dubai floating hotel in 2008. It was an entirely different kind of luxury experience. There was something wonderfully nostalgic about being on board, and the ship itself was simply magnificent. It was one of those rare journeys that stays with you long after you’ve returned home.
Do you have anything to add?
JG: I’d just add this: I don’t believe luxury is a category. It’s a feeling and it’s different for everyone. My goal isn’t to sell the most expensive trip. It’s to figure out what “extraordinary” looks like for each particular person, at that particular moment in their life, and then build it for them. When a client comes back and says, “I couldn’t have done this without you,” it hits home because that’s the whole point of being a trusted travel advisor – and honestly, it’s the best job in the world.
DW: When I entered the travel industry, I did so out of pure love and genuine adoration for what I do. Through the trials and tribulations we’ve witnessed, the Gulf War, 9/11, COVID, and the countless other challenges and catastrophes the world has faced, my love for this work, and for travel itself, has never faded. If anything, those moments have only deepened my appreciation for what travel can mean: connection, discovery, perspective, and the promise of somewhere new.
I’m nearly four decades in, and I’m still just as excited about the road ahead as I was when I first began. There is something truly special about a career that continues to inspire you, year after year, and I feel incredibly fortunate that travel has been that journey for me.
