I’ll be honest with you. I was a bit nervous about going to Alaska. I had never been to the state! I was a little nervous about the cruise and traveling with a group of people I mostly didn’t know. I wasn’t sure what to expect my anxiety was a bit high. Those that know me, know that I’m an anxious traveler and tend to be a homebody.
I know that probably sounds weird coming from a dude who hosts a podcast, runs community meetups, and talks to strangers about money for fun lol, But there’s something different about being in a group travel situation for the very first time. You just don’t know the dynamic. You don’t know if you’ll click with people. You don’t know if you’ll kinda feel like the odd one out while everyone else seems to already have their crew!
I’d been on a couple cruises before. But those were music cruises. Think Black Sabbath blasting through the main dining room. Think Metallica fans everywhere you turn. That’s its own kind of community, and I love it. This was different. This was the FinTalks cruise, organized by the amazing Amberly Grant, and it was my first time joining the group for anything like this.
I’ll let you in on a secret, I came home lighter than I left. And I didn’t expect that.
What Is FinTalks, Anyway?
If you haven’t heard of FinTalks, here’s the quick version. Amberly Grant built it as a paid membership community, a safe space where people gather weekly to talk about money, life, and financial independence. Sometimes it’s the members talking with each other. Sometimes Amberly brings in guest speakers. Either way, it’s not your average Facebook group where anyone can wander in and start throwing hot takes around.
It’s a smaller, more intentional membership group. People who are there actually want to be there. They’re curious, they’re thoughtful, and they’re genuinely trying to build better lives on purpose.
On top of the weekly community calls, Amberly plans trips. Like legit, real trips. We had nearly 90 people from the group on board this Alaska cruise. It kinda sounds like a lot until you realize how quickly that becomes a family when everyone already speaks the same language about money and life.
Seattle First: Space Needles and Blown Minds
I flew in a day or so early and spent some time in Seattle before the ship even left the dock. I had never been to Seattle before, and I hit the Space Needle and then wandered over to the Chihuly Garden and Glass museum, which is right there in the Seattle Center.
If you haven’t been to Chihuly, go. Seriously. I don’t care if glass art doesn’t seem like your thing. Dale Chihuly’s work is something else entirely. These massive, impossibly intricate glass sculptures in every color you can imagine, lit up and displayed in a way that makes you stop mid-step and just stare. I walked through that place slower than I’ve walked through anything in a long time. It was genuinely one of the most visually stunning things I’ve seen. And they had a live glass blowing demonstration, that was so cool to see them explain and walk through the entire process of what glass art, and glass blowing can be like! That afternoon set a tone for the whole trip without me realizing it. Slow down. Look at things. Be present.
The Ship, the People, and What Actually Happened
We set sail and the thing that hit me almost immediately was how easy everyone was to be around.
No drama. No cliques. No awkward energy from people trying to impress each other or perform status. Just a bunch of intentional humans who’d already opted into a community built around honest conversations about money, freedom, and life.
I had so many conversations over those days. Not like lame small talk about the weather or “so what do you do?” But, Real conversations. The kind where someone says something and you find yourself thinking about it three days later. We talked about health, fitness, retirement, what it means to actually live well, time buckets, regret minimization, and yeah, sometimes we just talked about food and music and random stuff that made us laugh until midnight. We also would hang out and play card games and board games every night!
There was always something going on, and people you could hang with. Some would message the group and invite people to the hot tub, or a morning run, or to meet for lunch or a snack or just to see the sunset from the deck! There was always something, and it was great!
Kevin, my buddy who was lucky enough to share the cabin with me on the trip, said something early on that stuck with me. He told his wife he wasn’t going on a cruise to Alaska. He was going on a cruise with a bunch of friends that just happened to stop in Alaska. That reframe is exactly right. The destination was almost secondary to the people!
And coming from someone who had just done the Monsters of Rock cruise the month before, where you could be surrounded by a thousand people and still barely talk to three of them in five days, the contrast was wild. Community changes everything about the experience.
Juneau, Fishing, and the One That Got Away
Our first port stop was Juneau, Alaska. I signed up for a fishing excursion because when you’re in Southeast Alaska, you fish. That’s just the rule! lol The weather was a rainy but it was still rad!
Did I catch anything? Nope. Not a single fish cooperated with my presence. And one thing I learned when traveling to Alaska was to ALWAYS prepare for rain, wind and cold I guess?! ALWAYS!
Yeah, so my fishing excursion was not REALLY what I expected as it was very cold, very wet and very windy. I didn’t know I was supposed to bring full-on rain gear, boots, gloves and shit! Many of the other cruisers that went biking, canoeing, or kayaking were provided gear from the outfitter. That was NOT my case however. So I got back from my fishing trip frozen to the bone completely drenched and ready to pass out. It was an ADVENTURE for sure!
Skagway: Rustic, Wild, and Kind of Perfect
Skagway is raw and real. This little Alaskan town looks like it stepped straight out of the Gold Rush era and never fully updated. Like we were back in time! The buildings, the streets, the mountains pressing in on every side. It’s one of those places where you walk around slowly and just take it in. Sometimes the activity is just the excuse to be somewhere and be present.
A few of us explored on foot and I kept finding myself stopping just to look up at the mountains. There’s something about that kind of scenery that quiets the noise in your head. Being a Minnesota boy, it was just amazing! No agenda, nowhere to be, just walking and talking and being somewhere genuinely beautiful.
Victoria and the Zipline That Changed My Mind About Heights
Victoria, British Columbia, is one of those places that looks like someone turned the charm dial up to eleven. We rented scooters and just rode around the city and by the water! I’ve learned that this is one of the best ways to actually see a place instead of just passing through it. I’ll most likely do this in the future.Â
But the real moment was the Zipline Adventure! A few of us signed up for a zipline adventure in Victoria, and I’ll be real, I wasn’t sure what I was getting into. I’ve never been, but once you’re up there, you go. And it was genuinely one of the highlights of the entire trip. The rush of it, the views, the shared adrenaline with the group afterward. That’s the kind of thing you can’t manufacture. You just have to say yes and show up. The crazy part was when I had to be rescued from one of the ziplines! Yes. Let me explain. There were a series of eight ziplines through the woods. The longest one was 1000 feet!
Anyway, on like the 3rd Zipline, I think it was like 530 feet long, I was coming in to the end platform and lost enough momentum that I was reaching out and couldn’t quite reach the guide that was helping everyone get to the platform at the end of the line. Sooooo, then what happens? I start to roll backwards on the zipline and there I am just at a dead stop dangling from the line lol.
This guide jumped into action. She quickly shimmied the line out to me and hooked a rescue line up to my trolly that was on the line, and using only her upper body strength had to hand over hand tow and pull me back to the platform! It was amazing! And the peeps I was with didn’t leave it alone ensuring to bring it up every chance they could lol.
The Conversations Were the Whole Point
If I had to name one thing that made this trip different from anything I’d done before, it’s the conversations.
It wasn’t the ports. Not the ship. Not even the zipline, which again, was awesome. It was just the hang time with so many people and the conversations.
I talked to people I’d known for years, I talked to people I’d just met and felt like I’d known them for a long time. We talked about what financial independence actually means when you have it. We talked about health and the idea of doing the hard physical stuff now, while you can, so you’re not sitting on the sidelines at 65 wishing you hadn’t waited. We talked about regret and risk and what it actually costs you to play it safe all the time.
One conversation in particular, with a 31-year-old guy I’d just met, hit me harrrrrd. He called this his “year of experiments.” He was committing to trying things he’d normally skip, just to see how he felt. His whole thing was that he didn’t want to get to 70 and realize he never tried the things that mattered. I’m going to be thinking about that for a while.
Rounding It Out: The Mandalorian, Old Friends, and a Soft Landing
After the cruise wrapped up, a few of us went to see the new Mandalorian and Grogu movie together. Look, I don’t need to oversell this. It was just a fun, easy, zero-pressure way to close out the trip with people I’d spent a week getting to know better. Low key and genuinely fun.
Then I met up with some friends in Seattle for lunch to have amazing fish and chips, before finally pointing myself back toward Minnesota. That lunch was exactly the right decompression. Good people, good food, no agenda. A soft landing after over a week of full-on.
What I Actually Took Away From All of This
Here’s where I land after thinking about it for a while:
Intentional travel hits differently. Going somewhere with a group of people who share your values and your curiosity changes the texture of the whole experience. It’s not just sightseeing. It’s connecting with people at a level that most travel doesn’t get close to.
The room doesn’t matter that much. I heard this from someone on the ship who had an inside cabin on one of the lower decks. No window, no balcony, no frills. And they were having just as much fun as anyone with an ocean view suite. Because the fun wasn’t happening in the room. It was happening everywhere else.
Do the hard stuff now. Watching people on this trip who were in their 60s and 70s still hiking, still climbing stairs instead of taking the elevator, still showing up with energy and curiosity, it was a reminder that the choices you make right now while you are younger about health and activity are the ones that determine what your future looks like.
Community is not optional. I used to think I was pretty good at going at it alone. This trip showed me maybe I’m better with people around me. Not just any people. People who are intentional, curious, and genuinely interested in living well. Finding that community is worth it. Stepping outside your comfort zone and finding your tribe.
Try the thing. Say yes to the zipline. Book the cruise with strangers. Sleep on the lower deck. Eat snails! (Yum!) The regret of not trying is almost always heavier than the discomfort of doing.
Would I Do It Again?
I came into this trip as someone who’d never traveled with a group, who wasn’t sure what to expect, and who was quietly wondering if I’d feel out of place. I came home re-energized in a way that I genuinely didn’t see coming. I could see myself doing this again.
I’m already thinking about how to build more intentional travel into the way I move through the world. Not just vacations. Experiences. With the right people. In places worth showing up for.
If you’ve been thinking about any kind of community travel, stop waiting. The people you meet on a trip like this will be in your life for a long time. That’s worth more than whatever’s in your savings account that you’re nervous about spending.
Horns up, my friends. 🤘 I’ll see you in our travels!