Welcome to all the new readers, and thank you to everyone who has been here for a while. I genuinely enjoy putting these newsletters together and sharing stories, thoughts, and travel lessons that do not always fit into a regular post on the site.
This week, I want to talk about getting started with travel — and why I think many people overcomplicate it before they even leave home. I know I have.
You Don’t Need to Know Everything Before You Travel
When I was a kid, there was a chef on TV I used to watch — Martin Yan. Every episode, he’d say the same thing:
“If Yan can cook, you can too.”
That line stuck with me. Honestly, it’s how I feel about train travel.
If I can do it, you can too.
You don’t need to become an expert before your first trip.
My first trip is proof.
I used Google Maps to drive from work to the Sturtevant Depot. Once I reached an area I recognized, I turned it off because I figured I could get there from there. I should have researched where the station was instead of relying on my own judgment.
I drove right past the station.
Eventually, I pulled into the spot where the station used to be, turned Google Maps back on, and headed back.
And here’s the thing: I didn’t need to research sleeping accommodations or business class for that trip because neither is available on the Hiawatha. The trip itself set the limits on what I needed to know.
But many new passengers don’t see it that way.
They spend hours researching:
Luggage
All the accommodations
Delays
Stations
Food
Safety
Packing lists
Travel hacks
Before long, they’ve got 50 tabs open and feel more overwhelmed than excited.
Research helps — until it doesn’t.
Not every tip online applies to your trip. Some advice is outdated, and some comes from people sharing unusual experiences that probably won’t happen to you. Sometimes, reading too much just makes travel feel more complicated than it really is.
Find one or two sources you trust and stick with them unless you truly need more information. Doing so can help you avoid analysis paralysis.
Years ago, I used Amtrak forums to find answers. This was before there were many websites like mine or many YouTube videos about train travel. Sometimes I found helpful information. Other times, I encountered trolls, negativity, and people who made train travel seem far more intimidating than it actually is.
Don’t let someone else rain on your parade.
That said, showing up completely unprepared creates its own problems.
The Short List That Actually Pays Off
Understanding baggage rules and the basics
Arriving early
Downloading or bringing entertainment
Checking your train’s status
Knowing what kind of seat or room you booked
And one of my favorite travel tips: bring an extension cord.
But the biggest thing is figuring out what you need to know versus what you want to know — and prioritizing accordingly.
Over time, I’ve become a strong believer in “just-in-time learning.”
Instead of trying to learn everything at once, focus on the next step in front of you. Then let your trip guide what you learn next.
That’s one reason my schedule and route guides are structured the way they are. You get the basics in one place, and if you need more information, there are resources to help you dig deeper.
When booking your trip, learn enough to choose the right train and accommodations.
Before departure, figure out what to pack and how boarding works.
Once you’re on board, you’ll quickly get the rhythm of train travel.
You don’t need to know everything before your first trip because some things can only be learned by actually doing them.
Even after hundreds of train rides, I’m still learning — and so is every experienced traveler I know. Things are always changing, and not every change is announced.
Travel isn’t about being perfect or knowing every detail in advance.
It’s about being willing to learn along the way.
Sometimes the best thing you can do is stop researching what you don’t need to know, book the trip, and start the adventure.
The Hiawatha is pulling into the station
What is Kev Up To?
For the past few weeks, I’ve talked a lot about my September trip, but not much about the booking process. That has finally changed. I now have the train portions booked, though I may still adjust one date.
Hotels are costing a little more than I’d like, but since part of this trip involves staying with friends, I may extend that portion by an extra day instead of spending more time in New Orleans. Honestly, I’m perfectly okay with that.
On Tuesday, one of my friends celebrated a birthday and wanted to go to a Brewers game. Yay… sports ball.
I’m not a huge baseball fan — I don’t really watch or follow the sport — but going to a game in person with friends is always a good time. Fun side note: I’ve sung the National Anthem at American Family Field twice with the University of Wisconsin–Milwaukee Men of Song choir.
We had a great time, and to make it a proper Wisconsin evening, we enjoyed a couple of beers and a brat. The Brewers won!
Thank You!
Thanks for reading! Thanks to Rebecca M for hitting the green tip button! If you hit that button and reply to the email, I will send you a postcard. This also applies to those who use PayPal.
If you're interested in helping me continue, you can click the green button below, visit my support page for more options, or join my Patreon! With a paid Patreon membership, you get a monthly postcard and more, and I just ordered new postcards.
Until Next Week!
Safe travels & Happy Planning, Kev Monteith
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Travels with Kev is independent and not affiliated with Amtrak or VIA Rail. The tips and information here are based on my personal experience. Always verify Amtrak's and VIA Rail's current policies, deals, and schedules before booking.
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