There’s a special kind of joy in looking ahead to a trip you’ve been waiting for, knowing the suitcases aren’t packed yet, the lists are still scattered, but the countdown has truly begun.
In just a few weeks, I’ll be on my way to Alaska for my very first cruise. It’s a trip that combines celebration, adventure, and family. And while I’ve traveled plenty over the years, this one feels different. It’s not just about where we’re going, but how we’ll experience it together.
A Family Celebration
The heart of this trip is a family celebration. I don’t often get the chance to spend meaningful time with my mom and my sisters; it’s been years since we’ve had that kind of space together. That alone makes this journey deeply special, especially because the four of us have planned a photo shoot while we’re there, something we’ve never done before.
I’ll be traveling with my family, and having us all together for this milestone feels like a gift. We’ll be celebrating my mom’s 80th birthday, and while Alaska will also mark my 49th state, that’s just a fun side note. The real reason for this trip is her, and being together in a way that’s increasingly rare as life moves forward.
Why Cruising, Why Now
Cruising is something we’ve always wanted to experience, but other trips and priorities always came first. This year, the timing lined up perfectly. Alaska felt like the right fit for my mom’s milestone celebration, and a cruise offered a way to experience it without juggling multiple hotels, transportation logistics, or meals for a group.
Normally, our vacations are packed with activity: exploring new foods, sights, adventures, and learning about the area in depth. This cruise will have plenty of that, but it also comes with something new for us: built-in stillness. I’m looking forward to moments when the “adventure” is simply sitting on the balcony with coffee, watching the scenery drift by. It’s a different kind of travel for us—one that blends exploration with quiet, something we haven’t tried before.
Planning When I’m Not the Planner
A big part of the fun of travel for me is the planning. I love the research, the mapping out of possibilities, the anticipation that comes from building a trip piece by piece. When I plan, I arrive feeling ready, knowing I have a menu of options to feed my (lack of) spontaneity. I don’t need a down-to-the-minute schedule, in fact, I prefer not to have one, but I do need those 18 backup ideas tucked in my back pocket.
On a packaged trip like this, someone else is doing the planning. It’s freeing in some ways, but it also means I don’t have that same anticipatory joy. My FOMO tends to show up in real time instead, because I haven’t done the deep dive beforehand to understand what’s out there. That’s new for me, and it’s going to be an interesting adjustment.
Planning the Excursions (and the Spreadsheet That Saved My Sanity)
While I wasn’t going to book excursions outside of what the cruise line offered, choosing between their options was a whole different story. Norwegian’s app made it surprisingly difficult to compare excursions. It felt scattered, like trying to assemble a puzzle without the picture on the box.
So, of course, I did what I do best: I built a spreadsheet.
It gave me a way to see all the options side by side (Related: The Pigeonhole Paradox) — on why it’s so hard to let go of the planning role even when you try.), categorize and compare them clearly, and make sure we weren’t doubling up (i.e., glacier, glacier, glacier) in every port. It also let my family see what we were considering, so if anyone wanted to join in on an activity, they could easily do so.
Here’s what we landed on:
- Juneau: Gardens, Hatchery, and Mendenhall Glacier
- Skagway: White Pass Railroad
- Ketchikan: Local brewery tour (yes, at 10 AM, day drinking at a whole new level!)
The spreadsheet didn’t just help with logistics, it gave me a sense of calm. Even when I’m not officially in charge of planning, I need some structure to feel grounded. Once that’s in place, I can let go and truly enjoy the moment.
The Surcharges and Surprises
One thing I’ve noticed about packaged vacations is how many little extras show up along the way. Shore excursions, specialty dining, gratuities, internet access — the list feels endless.
I don’t mind paying for quality experiences. Years of planning Disney trips have trained me well for a bit of nickel-and-diming. The difference here is that with Disney, I know exactly what I’m getting for every add-on. With cruising, there’s still some uncertainty about value. It’s a minor point, but for a planner, that uncertainty is what makes the add-ons feel like a game of chance instead of a known expense.
Take the “More at Sea” program, for example. It includes an unlimited drink package… with a small asterisk. Drinks are unlimited as long as they’re under a certain price. My mind went straight to bottom-shelf nightmares, but thankfully, most of my go-tos were on the list, though there are a few top-shelf options that cost extra.
It’s not a complaint, more of an adjustment. Nothing’s ever going to be perfect unless you design it yourself, and this trip is about leaning into the experience and letting those little quirks roll off my back.
Time Together, Differently
Dan and I spend a lot of time together at home. We both work remotely, our kids are grown, and we genuinely enjoy each other’s company. This trip isn’t about carving out time, we already have that. It’s about sharing a new adventure together.
Looking Ahead
Right now, my suitcase isn’t packed, and my lists are half-finished. The planning phase may not look the same this time, but the anticipation is still very much there.
Soon, I’ll trade spreadsheets for sea breezes and to-do lists for tide charts. When I finally sit on that balcony, coffee in hand, watching the Alaskan coastline slide past, I hope I’ll remember this exact feeling — the thrill of standing at the edge of something new, ready to see where the journey takes me.