Marylander Goes to Alaska. Here's What Happened.

Docked in Juneau, Alaska with a view of buildings under a towering green mountain

A personal essay from Wendy

I've been a travel advisor long enough to know that sometimes the destination you've been selling becomes the destination you need to actually visit.

Alaska was that destination for me.

I'd been telling people about it for months. The scale. The glaciers. The wildlife. The way a small ship changes everything about how you experience it. I knew Alaska intellectually - the statistics, the itineraries, the shore excursions, the best ports for each traveler type. I had prepared other people for it with great confidence.

And then I got there.

I come from Maryland. We call it America in Miniature - a tiny state that somehow packs almost every major U.S. landscape, historical era, and demographic mix into a very small area. I've always been proud of that. Maryland punches above its weight.

Alaska surprised me. Nothing about Alaska is miniature!

Nothing I read or researched or said to clients adequately prepared me for the scale of the place. The state itself is enormous. They tease Texas about being "cute!" Denali National Park alone is six million acres. Six million. That’s bigger than the entire state of New Hampshire. We thought we'd drive right up to Mount Denali, the way you can pull up to El Capitan in Yosemite. Nope. The road doesn't go anywhere near it. You spend six hours on a tundra wilderness bus, scanning for bears and moose and dall sheep - tiny white polka dots on distant mountain faces - and you still see less than one percent of the park.

Our ship, the Azamara Pursuit, is considered a small ship. And it felt small. Genuinely, wonderfully small - sailing through the ferry passages of the Inside Passage with towering fjord walls rising on both sides of us, the landscape leaning in like it was curious about us. The tiny port towns tucked into those fjords - you could walk end to end in less than an hour, but they were packed with culture, heritage, history, art, food, and genuinely some of the nicest people I've ever met.

The crab legs are enormous. The whale flukes are enormous. The animal prints we found in the mud were enormous. Even the sky feels bigger in Alaska - like someone stretched the horizon out in every direction just to give you more room to look.

It puts things in perspective in a way that's hard to explain until you've stood in it.

I had been telling clients about Hubbard Glacier for months.

As we approached it on the ship, I had a quiet moment of panic. What if it doesn't live up to everything I've been saying? What if I've oversold it? What if reality can't match the picture I've painted?

It matched the picture. And then it exceeded it.

Hubbard Glacier viewed from the veranda of the Azamara Pursuit in Alaska

We got there a bit early - warm hats, gloves, and blankets claimed on the sunloungers at the very forward top of the ship. Azamara had thought of everything. Cozy blankets on deck. Hot drinks for everyone. Our captain got us within three miles of the face, which sounds like a lot until you realize it’s size - 76 miles long, seven miles wide, and 600 feet tall at its terminal face. And growing. Advancing, not retreating.

The captain spun the ship 360 degrees - slowly, deliberately, multiple times - so that every single person on board, no matter where they were standing, got the full view. I thought about that decision afterward. It cost time. It required patience. And it meant that nobody missed that perfect view of the glacier. That's a philosophy, not just a maneuver.

The glacier calved while we were there. Multiple times. They tell you it's thunderous and impressive. They're right. You don't just hear it, you feel it in your chest. Every time it happened, the whole deck reacted. Strangers sharing something. Nobody looking at their phones.

I took approximately one thousand photos. I still don't think I captured it.

Next time, I want to do an excursion right up to the face of the glacier. Because Hubbard didn't check a box. It opened a door.

I went to Alaska with a list.

On that list - salmon jumping upriver. We'd seen the videos, heard the stories, and we knew it was the season. We stopped at every river, every bridge, every spot where it was supposed to happen.

We never saw a single salmon. Not once.

Alaska doesn't perform on demand. And learning to make peace with that turned out to be one of the best things that happened to me on the trip.

Our captain on a whale watching excursion in Juneau got word before our tour that a group of humpbacks had been spotted bubble net feeding - a rare coordinated hunting behavior where whales work together, surfacing in a ring with their mouths open. The crew hadn't seen it all season. He went 30 minutes out of his way, each direction, to get us there.

We watched it happen. Something I couldn't have planned for. Something that wouldn't have been on any itinerary.

This is where I want to say something practical, because it matters: hire the knowledgeable guide. The ones who have been doing this for years, who know which coves the sea otters favor, which areas bears have been spotted before, which captains on the water they can radio for a tip. The Denali bear we spotted - seen through our bus driver's zoom lens, on a screen, from very far away - happened because another driver radioed ours with the location. That network is the difference between a wildlife trip and a wildlife experience.

And then - after you've hired the expert and trusted their instincts - let go of the list.

Because two of our friends on the cruise encountered a bear while standing in line at Jellyfish Donuts in Juneau. Not on a tour. Not in the wilderness. At a donut shop.

Black bear in the doorway of Jellyfish Donuts in Juneau, Alaska

Alaska is going to do what Alaska wants. Your job is just to be paying attention when it does.

I went to Alaska as a certified expert. I came back as a believer.

Not because it confirmed everything I already knew. Tthough it did. But because it surprised me in ways I wasn't prepared for, and those surprises were better than anything I could have researched.

The scale that makes you feel small and somehow more capable at the same time. The glacier that exceeded every expectation I'd spent months building. The salmon that never showed up and the humpbacks that showed up instead, doing something the crew had never seen that season.

Alaska reminded me of something I think we forget when we spend too much time optimizing our routines and managing our calendars: we are built for this. For adventure. For things that are bigger than our daily lives. For experiences that feel a little uncomfortable, a little outside the plan, a little bigger than what we're used to.

The best things don't show up on schedule. They show up when you stop demanding them to.

Go to Alaska. Let it be bigger than you expected.

It will be.

Alaska is our marquee destination - and The Alaska Shortlist is how we're going to get you there. Three sailings. Summer 2027. Two advisors who have now been exactly where you're going.

View The Alaska Shortlist → or reach out directly. We have a lot more to tell you now.

Next
Next

Notes from the Co-Founder Who Hugged a Bear