The Art of Traveling Your Way: A Personal Q&A with Lee Ann Howe
For Lee Ann Howe, founder and private travel advisor at Affluent Passport, an exceptional journey begins with a conversation.
A client might arrive with a destination in mind, a milestone to celebrate, or simply a feeling they hope to recapture. Lee Ann wants to learn what excites them, how they like to spend their time, and which details make a place feel like their kind of place. Then she can introduce them to possibilities they may never have thought to ask for.
That curiosity began in childhood, when travel with her father showed her how much there was to discover about the world—and how much people could discover about one another along the way. We sat down with Lee Ann to talk about the experiences that shaped her, the moments she loves creating for clients, and what luxury means to her today.
How did traveling aboard your father’s private plane shape your curiosity about the world?
I was fortunate to be introduced to travel at a young age. My father had a private plane, so going somewhere new was part of my childhood. But what stayed with me was his belief that seeing the world, experiencing different cultures, and meeting people would make you a more well-rounded person. He told me those experiences would take me further in life, whatever I chose to do.
I remember visiting Copenhagen with my parents and grandparents when I was in fifth grade. We were speaking with a store clerk who asked where we were from. When we said Indianapolis, an older Danish woman nearby lit up: “Like the Indianapolis 500? Vroom, vroom!”
She and the clerk watched the race every year. Suddenly, they wanted to know all about our hometown and what it was like to live in America. I had traveled to Denmark because I was curious about their world, and there they were, just as curious about mine.
I’ve never forgotten it. Travel can create a connection in the most unexpected way.
I still feel that same excitement when I arrive somewhere, even if I’ve visited many times before. I want to know, What haven’t I seen yet? My father gave me that curiosity. I shared it with my children, and now I get to share it with my clients.
Which client journey remains especially meaningful to you?
There are so many. Often, what I remember most is one moment within a larger trip.
In Rome, I arranged a private Vatican experience that included the Basilica and the Apostolic Palace. On another occasion, I planned a private dinner proposal overlooking the city. The setting was beautiful, of course, but what mattered most was creating a moment that felt entirely their own.
Then there was a birthday in Munich, where we went all in on a traditional Bavarian celebration. It was lively, authentic, and such fun. I love that kind of contrast. An unforgettable trip can include a deeply moving private experience and an evening when everyone is laughing.
I’ve also had the chance to travel with clients. Seeing a journey through their eyes teaches me so much: what draws their attention, what makes them happy, and which small details matter more than anyone might have guessed. It helps me make their next trip even more personal.
What separates an exceptional luxury journey from one that is simply expensive?
An expensive suite can still come with an ordinary experience.
To me, exceptional travel feels effortless. The people welcoming you know who you are. Your preferences have been shared. The timing works. You can enjoy the day without managing reservations, transportation, or the next change of plans.
And then there are the moments you wouldn’t necessarily have found or arranged on your own. I want a client to experience something and think, How did Lee Ann know I would love this?
That’s luxury to me.
Which shifts in luxury travel excite you most right now?
I love seeing people think more about the experience they want to have, alongside where they want to stay. I’ll always appreciate an extraordinary five-star hotel, but clients are also asking for private villas, yachts, private aviation, remarkable food, sporting and cultural events, and experiences that bring them closer to a destination.
They’re protective of their time, too. They want the freedom to be fully present while someone they trust takes care of the details.
And I enjoy seeing clients become more adventurous. There are incredible places beyond the destinations everyone already knows. Sometimes all it takes is the right introduction.
What’s at the top of your own travel list?
My list never gets shorter! Patagonia is high on it right now. I’m fascinated by Chile and Argentina—the landscapes, hotels, wine, food, and sense of adventure. Malta and Montenegro are calling to me as well. I’m drawn to places that still feel a little unexpected, especially when they bring together history, beautiful scenery, wonderful hotels, and a strong local culture.
I love places with energy. Of course I want to know about the beautiful hotel and fabulous restaurant. I also want to know where everyone goes afterward!
Europe will always have my heart. I can return to a city I know and still feel excited to turn down a different street. There is always something else to discover.
How do you learn what a client wants when they may not know how to describe it yet?
I tell my clients, “Eventually, I will know you better than you know yourself.” I say it with a smile, but I mean it.
I ask questions, and I listen closely. A passing comment can tell me far more than a form. I want to know whether someone loves being in the middle of everything or prefers complete privacy. Whether a full day of plans sounds exciting or exhausting. What kind of hotel makes them happy.
I remember the restaurant they loved three years ago, the room that felt too far from the lobby, the pleasure they take in coffee outside each morning, or their preference for a late dinner. Those details shape a trip.
My clients don’t need to arrive knowing exactly where they want to go. They can tell me how they want the journey to feel, and we can figure out the rest together.
What do access, privacy, and personalization mean to your clients today?
Access can mean seeing something privately before the doors open, but it can also mean meeting someone who brings a destination to life. It might be a dinner in an unexpected setting, an arrival by boat, or a villa where three generations can spend a week together comfortably.
Privacy means different things to different people. Some want complete seclusion. Others want to be at the center of the action, with everything handled discreetly around them.
The best personalization is often quiet. Your preferences are already known. The right people have been briefed. Everything is in place before you have to ask. You can simply enjoy where you are.
What advice would you give someone planning a milestone journey?
Give yourself time to enjoy it. You don’t have to change destinations every two or three nights or fit every possible experience into the itinerary.
I love when clients leave room for a long lunch, a neighborhood café they return to twice, or an afternoon with no plans at all. Longer stays let you get to know a place a little better. For a milestone trip, I’d ask: How do you want to feel when you come home?
Spend where it truly changes the experience, stay long enough to enjoy it, and leave space for something unexpected. Some of the best memories come from the afternoon when everyone changes the plan, finds a little restaurant, and stays for three hours.
I want my clients to come home saying, “I wish we could do that all over again.” That’s when I know we got it right!
Where Could Your Curiosity Take You?
The journeys Lee Ann remembers most are as varied as the people who took them: a private moment in Rome, a joyful birthday in Munich, a family discovering how good it feels to slow down together. What connects them is the care taken to understand the travelers before planning the trip.
Whether you have a destination in mind or only know how you want to feel when you arrive, Affluent Passport can help you begin the conversation. Your most memorable journey may start with a possibility you haven’t considered yet.
Affluent Passport. Private travel, without compromise.
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