When most people picture a travel advisor’s day, they imagine sipping coffee while casually clicking “book” on a few flights and hotels.
In reality? It’s equal parts puzzle, strategist, storyteller, and air traffic controller — all wrapped up in one very well-organized Google Sheet.
Recently, I worked with a family planning a multigenerational Alaska cruise — grandparents, adult kids, and young grandkids. This is my favorite kind of trip to plan because it’s about more than logistics. It’s about crafting a shared experience across generations, something they’ll talk about at family dinners for years.
☀️ Morning: The Foundation
My work window starts early, and the first thing I do is review my notes and trip vision for the family. Every client call ends with a clear picture: what matters most to them, what pace they prefer, and any special touches they want to include.
For this family, the priorities were crystal clear:
- Grandparents wanted a bucket-list Alaska experience without feeling rushed.
- Parents needed kid-friendly activities and smooth travel days.
- Kids were excited for wildlife, glaciers, and “sleeping on a boat like Moana.”
I opened up my planning dashboard, mapped their preferred travel dates against the major Alaska cruise itineraries, and started narrowing options. Some ships offer jaw-dropping glacier viewing but limited kids’ programming. Others are fantastic for families but don’t hit the most scenic routes. I had to find the sweet spot.
☕ Midday: The Puzzle Comes Together
Once I’d shortlisted the best itineraries, I dove into cabin configurations. This is where multigenerational trips can get tricky: do you cluster rooms together or split between decks? Suite or verandah? Who gets the best view?
I layered in loyalty perks, promos, and onboard credits — then crafted two complete options that hit their wishlist and their budget. No decision fatigue here; just two strong choices, both wins.
Next came the excursions. Grandma had always dreamed of seeing whales up close. The parents wanted something active, like a guided hike. The kids? Sled dogs. (Obviously.) I built a custom excursion plan that balanced these priorities without over-scheduling any day.
🌙 Evening: The Magic Touches
Before I wrap, I always ask myself: If this were my family, what would make this unforgettable?
For this trip, it was arranging a private family dinner with glacier views, plus a pre-cruise hotel stay in Seattle to make travel easier for everyone. Little details like that turn a trip into a memory.
When I sent the proposal, their response was immediate:
“This is exactly what we were hoping for.”
And that’s the part people don’t see in a “day in the life.” It’s not just about booking trips — it’s about understanding families deeply, anticipating needs, and building experiences that feel effortless when they’re living them.
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