Why Newly Retired Travelers Are Choosing Advisors Over Apps in 2026

By Kari Bradbury | Kingfisher Luxury Travel

View of the beautiful blue Lake Como, Italy.

Let me paint a picture.

It's the summer of 2023. I'm planning a 10-day trip to Northern Italy — Milan to Lake Como to St. Moritz to Venice to Florence — with my 17-year-old daughter, my 13-year-old son, and my older sister. Five destinations. Four very different personalities. Approximately four hundred opinions about how to spend each day.

My daughter is a natural-born itinerary architect. She wanted cooking classes booked, museums reserved, every hour accounted for. My son — a musician with a deep love of wandering and a gift for stumbling onto things nobody planned — wanted breathing room to discover. My sister and I were somewhere in the middle, just trying to hold the whole beautiful, chaotic thing together.

Oh — and I'm a travel advisor. I help people plan exactly this kind of trip for a living.

And I still called Schelli.

When Even the Expert Needs an Expert

Here's what most people don't understand about travel apps, booking platforms, and the endless rabbit hole of travel planning online: the information isn't the problem. There's more of it than you'll ever need. TripAdvisor. Google. Viator. Expedia. Instagram reels of someone's perfect afternoon in Florence. Annnddd....the TikTok. Oh yes - the TikTok.

They'll give you ten thousand options before breakfast.

The problem is judgment. The knowledge of which option is right for you — your pace, your people, your idea of a perfect afternoon. That's not something an algorithm can weigh. It requires someone who has been there, who knows you, and who can hold the competing needs of everyone in your travel party and shape them into something that actually works.

For my Northern Italy trip, that person was my business partner, Schelli Bettega — co-owner of Kingfisher and one of the most detail-oriented travel minds I know. Even though we collaborate on itineraries every day, having her as a second brain for my own family's trip meant the difference between a beautifully calibrated journey and a well-intentioned mess.

She helped us balance the competing itinerary philosophies in our group — structured days for my daughter, free hours built intentionally into the schedule for my son and me, and anchoring experiences in each city that would resonate across all four of us regardless of age or temperament. It wasn't magic. It was expertise applied with care.

The Moment That Surprised Us All

I can tell you exactly when I felt it most.

We were in Venice — which, if you've been, you know, requires no embellishment whatsoever — and we attended a performance of Vivaldi's Four Seasons at the Scuola Grande di San Teodoro, a breathtaking 16th-century Venetian concert hall just steps from the Grand Canal.

Now, my son is a musician. He was always going to love this. I knew it the minute I saw it on the itinerary. But my daughter — structured, art-focused, more interested in a Uffizi Gallery deep-dive than a classical concert — I expected her to be politely present. Graciously tolerant. Daughter-on-a-family-trip energy.

Instead, she was transfixed.

We all were. Performers in period Baroque costume. Strings that seemed to fill the centuries-old room from the floor upward. The music of a composer who was born and lived and breathed Venice, played inside the very city that made him. My son sat completely still — which, if you know any 13-year-old musicians, tells you everything. My sister leaned over at some point and said something I've thought about ever since. I don't remember the exact words. I just remember thinking: this is it. This is the moment the trip became theirs.

No app recommended that concert for us. No algorithm weighed my son's love of classical music against my daughter's skepticism and said: trust us, this one lands for everyone. That came from a human being who knew what we needed — even when we didn't.

Why This Matters for Newly Retired Travelers

If you're recently retired — or you can see retirement clearly on the horizon — you are standing at a genuinely extraordinary threshold. You have, perhaps for the first time in your adult life, the time and the means to travel the way you've always imagined. Not a rushed long weekend. Not a conference with stolen bookend days. A real trip. One that was designed for you.

And here is what I want you to know: this is exactly when the stakes of getting it right become highest.

Not because the money is significant — though of course it is. But because the time is significant. You've spent decades earning this season of your life. A trip that falls flat because the hotel wasn't quite right, or the pacing was exhausting, or three out of five excursions were ones you could have done anywhere — that's not just a disappointing vacation. It's an opportunity cost measured in something more precious than money.

This is why, in 2026, the travelers who invest most thoughtfully in their experiences — not just the most lavishly, but most thoughtfully — are increasingly turning away from booking platforms and toward trusted advisors. Not because apps are bad. But because apps can't do this:

They can't ask you what you're hoping to feel on the last night of the trip. They can't remember that you mentioned your husband loves architecture and your best friend gets motion sick on small boats. They can't notice that your itinerary has four consecutive heavy-sightseeing days and quietly rebuild it before you've even noticed the problem. They can't call the property directly and make sure the room you're in faces the water because they know you'll want to sit on that balcony at dawn with your coffee.

Schelli and I can. That's the whole point of Kingfisher.

What "Curated" Actually Means

The word gets used a lot in luxury travel, and like most overused words it has started to lose its meaning. So let me tell you what it meant for my family in Northern Italy in 2023.

It meant my daughter had a cooking class in Florence she still talks about. My son and me had an afternoon in Milan with no agenda, no schedule, and the specific instruction to get lost and report back. It meant my sister and I had a long, unhurried lunch on Lake Como that nobody photographed and all of us will remember. And it meant four people — ranging in age from thirteen to however old my sister is (she reads this blog, so I'll stop there) — sat together in a candlelit Venetian concert hall, completely still, completely present, and completely united in being amazed.

That is what a great travel advisor gives you. Not just a beautiful itinerary. The conditions for the moments that matter.

Your Next Chapter Deserves This

If you've been doing your own travel research — building spreadsheets, comparing hotel reviews, trying to reconcile seventeen browser tabs into something resembling a plan — I want to offer you a different experience.

At Kingfisher, Schelli and I work with a small number of clients each year. We specialize in luxury journeys, river and ocean cruises, multi-generational travel, and milestone experiences — and we bring to every single trip the same thing we brought to my family's Northern Italy adventure: genuine investment in making it yours.

The first step is simply a conversation. There is no obligation — just the chance to tell us about the trip you've been imagining, and to hear what's possible when someone who has actually been there helps you design it.

Schedule your Discovery Session or Consultation.

Your next chapter is waiting. We'd love to help you write it.

Explore the world with insight.

— Kari

---

Kari Bradbury is a co-owner and luxury travel advisor at Kingfisher Luxury Travel, a women-owned boutique travel advisory specializing in bespoke journeys, milestone celebrations, and luxury cruises. She is certified with Viking Ocean, Viking River, and AmaWaterways, and is an active member of CLIA and ASTA. Learn more about Kari and Schelli — or schedule your Discovery Session to start planning yours.