Back in fall 2025, when I was booking a Princess sailing for a couple, I put them on the left side of the ship.
They never asked why. They didn’t even know it was a decision.
It was a 10 day land and cruise package, the Denali Explorer, July 2026, sailing southbound. Nothing about the itinerary told them to care about left versus right. Most people don’t think about it at all. They pick a cabin category, maybe a balcony over an inside room, and call it done.
The detail nobody thinks to ask about
But on a southbound Alaska cruise, the side of the ship you’re on determines what you watch out your window every single time you pull into port. Get it wrong and you’re staring at open water while the mountains and the town slide by on the other side of the boat.
They called me after the cruise. I remember exactly what she said: “Oh my god, it just amazes me that you knew to put us on that side of the ship. It was amazing. Every time we were coming into port we could sit on our balcony and watch the ship dock. It was just amazing, and something I never would have even thought about, but you knew exactly what we needed.”
That’s not luck. That’s not a coin flip that happened to land right.
Why I knew
I hold the Travel Alaska expert certification and the Alaska expert certification through Princess Cruise Line. Part of what that actually means, practically, is knowing things like this: which side faces the port on a given sailing direction, which side gives you glacier views instead of open channel, which side means you watch your ship maneuver into Juneau instead of watching Juneau’s parking lot.
It sounds small. A cabin side. But it’s the difference between a trip where you experienced Alaska from your own balcony every single day, and a trip where you had to walk to the other side of the ship and hope there was room at the rail.
What this actually means when you’re booking
Here’s what I actually think when people ask me about planning an Alaska cruise: the itinerary matters. The cruise line matters. But the person planning it for you might matter more than both of those combined, because the itinerary doesn’t tell you which side of the ship to book. A booking engine doesn’t tell you that either.
That couple never requested the left side. They didn’t know it was on the table. I booked it because I knew what it would give them, before they ever became my clients enough to ask me for anything.
That’s the part I actually want you to take from this. Trust in an advisor shouldn’t come from a sales pitch. It should come from what they do when you’re not even watching, the calls they make on your behalf without needing to be asked. This one happened to be about which side of a ship. The next one might be about a shore excursion, a dining time, a port day nobody warns you gets crowded. You won’t always know what those calls are. That’s kind of the point.
This is one detail, on one sailing. I’ve got dozens more like it for other itineraries, other ships, other ports, the kind of thing that only comes from planning Alaska cruises this closely for this long. If you’re comparing cruise lines and cabin categories on your own right now, I’d rather just tell you what I know before you book something that gets it backwards.
May adventure follow you wherever you may go.