My first Amtrak adventure began on May 25, 2012, and it changed my life, although I wasn’t aware of it at the time. My Amtrak travels let me see things I would never have seen otherwise, meet some fantastic people, and have experiences I never thought I would.
Due to my Amtrak adventure, the train took me to places such as New Orleans, which I had not initially planned to visit, but I went anyway because I wanted to ride a particular train. Now, places like these are my favorite! On the other hand, I also experienced impostor syndrome when it came to travel.
I Did Travel Before This Trip.
My travel life can be divided into four phases, each serving as a building block for the next adventure.
In Phase One, from birth to eighteen, my parents taught me basic travel skills, such as visiting family and taking day trips. However, I don’t recall receiving hotel rooms or trips like those to Disney. My paternal grandparents took trips when I was young. These are memories that have stuck with me!
Phase two began at age 18, when I purchased a 1990 Oldsmobile Silhouette, which I used for numerous road trips and as a bike carrier for cycling tours. I learned to enjoy solo travel during this time, and I still cherish it.
In phase three (twenty-five to thirty-five), I didn’t travel much, but I learned the basics of public transportation. This article covers Phase Four, which began with a single train trip and culminated in my traveling across the country.
In Phase Four, I have traveled on all but one of Amtrak’s long-distance routes, most of the Midwest regional routes, and coast-to-coast by both rail and air. Phase four starts with this story.
Don’t Drive Down Here.
In 2012, my friend Pete moved to Chicago and invited me to an event we could attend and hang out at. He was kind enough to let me stay with him, but he had a caveat for my visit: don’t drive down.
His logic was solid: Parking in downtown Chicago is expensive, and parking near his place was a premium. I owned a 1989 Chevy Celebrity, not a tiny car, but not a land yacht.
He suggested taking the train down, either Amtrak or Metra. Since I was coming from work, Amtrak became my choice because it was closer.
Pete had taken the train a few times before so that he could share his experience with me.
I have driven to the Windy City before, but the idea still stresses me out. On the other hand, I had never done anything like this before, but Pete assured me it was easy and comfortable, so I trusted him.
I did the research and booked my first Amtrak Adventure.
Since I decided to take the train, I had to do some research, which started with a visit to Amtrak.com. There, I found the Sturtevant Station. This station was a great choice because it was a reasonable distance from work, not too far from home, and had cheap parking.
Soon, I had the Amtrak app on my phone, signed up for Amtrak Guest Rewards, and booked my round-trip on Amtrak’s Hiawatha.
With Pete as a guide, I would not get lost—at least, that was my hope. I have experience with Milwaukee’s mass transit system, using buses, but the CTA is slightly different.
I know where the station is; apparently, I didn’t
The day of travel came, and I was ready for my first Amtrak adventure! I packed my bag and threw it in the car. My shift at work had ended, and I was punching out for the weekend, excited to head to Sturtevant.
Over the years, I have been through Sturtevant from home, but I needed Google Maps to get there from work. Now I use the app until I reach a familiar area, then I turn off GPS and navigate by memory. Great idea, right?
That was a mistake! I drove past the depot on a parallel road on the other side of the tracks, heading toward the former Milwaukee Road station. By then, the old station had been relocated to a park, and a Canadian Pacific Kansas City Southern building now occupied that site. At that time, it was referred to as Canadian Pacific. I’m not sure why I felt so confident; this was my first Amtrak ride!
So, I swallowed my pride, re-entered the station’s address in the app, and found the depot. After paying for parking and gathering my belongings, I headed to the platform, ready for my adventure.
Soon, an announcement came over the public address system, and the passengers at the station gathered for the train. A few moments later, the train stopped at the platform and picked us up for our 63-mile journey to the Windy City.
All Aboard!
Before boarding the Hiawatha, I had discovered another Amtrak newbie waiting for the train. So, between the two of us, we figured out what we were doing and when the train came. She and I climbed aboard and searched for our seats. We sat in a section reserved for those needing assistance, then moved back and enjoyed the trip.
The train had six coaches and was full but not packed. It took about an hour to get to Chicago. I loved the train’s motion and the sound of its steel wheels rolling on steel rails; they did something to my soul.
Watching the world go by was fun; before I knew it, the Chicago skyline came into view. When we reached Chicago, my travel buddy and I said our farewells and went our separate ways.
Chicago, Chicago, that toddling town.
Looking back, it’s amusing that I got confused and overwhelmed on my first visit to Chicago Union Station. These days, I know that station well and no longer find it confusing. After leaving the train,
Soon, I was up the escalator and out the door to meet Pete. It was time for Google Maps to guide me to Pete’s workplace.
I liked the trip.
After a fun weekend, I headed home and felt like I had mastered Amtrak’s Hiawatha.
That year, I visited Pete four times via Amtrak. Little did I know that something had happened to me on that first trip; the little wanderlust bug in my soul woke up again. Not only did that bug wake up, but it also likes train travel.
You might like San Francisco.
In late 2012, my friend Ben traveled to San Francisco, and after his return, he told me I might enjoy a trip there. Sometimes, people say something, and you ponder it in your heart for some unknown reason. I did that in San Francisco, which became my first cross-country destination!
Planning my first long-distance trip
My taxes were kind.
In February 2013, I worked on my 2012 taxes, and since student loan interest was tax-deductible at the time, I discovered I was getting a nice chunk of change back.
As Jean-Ralphio Saperstein of Pawnee, IN, would say, I was flush with cash (Parks & Recreation reference).
Maybe not flush with cash, but I had enough for an adventure.
I could have invested that money, but I decided to take a trip. I invested in myself; at least that’s how it seems.
The time came to start planning and researching again, and I discovered I enjoy it.
I talked to Ben again and asked him a few more questions about the City by the Bay. Because I enjoyed my short train trips, I thought, ‘Why not see if Amtrak could take me there?’ And yes, it could.
What my research told me
My research showed I could start at the Sturtevant Depot and transfer to the California Zephyr in Chicago. From there, I would ride to Emeryville, CA, and then take a bus to San Francisco.
I don’t want to say I’m cheap, but I’m happy not to pay retail when I don’t need to. In my research, I found NARP, the National Association of Rail Passengers, which is now known as the Rail Passengers Association.
After joining, I received 10% off the base ticket rate, and my membership fee covers nearly all of the savings.
If I took any more trips, I would start saving, and it’s a good cause!
New Amtrak Adventure: New Luggage
Since I had not traveled much, it was time for new luggage. My secondhand luggage was falling apart and impractical for this journey. Clueless about what was there, I turned to the big box and discount stores.
The hunt for a 24-25″ rollaboard ended with a walk to the clearance section of my store (I worked at a big box store then). Someone returned their online order for a set of four suitcases priced at $119.
After I checked out and used my discounts, I purchased the four-piece luggage set for about $40; I kept the 25″ and the small hand carry-on bag and sold the rest to my mom, so $20 for what I wanted wasn’t too bad.
From my experience, you get what you pay for with suitcases and luggage. Designer suitcases cost more but are often not significantly better than cheaper ones from the same company. However, I am sure that is not always the case. Looking back at my first trip, I discovered I traveled too heavily because I brought a full 25″ suitcase plus a backpack!
The start of my first long-distance Amtrak Adventure
The day of my Amtrak Adventure arrived, and I was excited. I booked my coach seat tickets, overpacked my bag, and arrived in Chicago.
Because of my excitement, I left early. I would rather wait at the train station or airport than at home.
By this point, I was familiar with Chicago Union Station. I had my favorite places to eat and wait. One of those places I enjoyed was a bar off the Great Hall. (The bar closed, and I cannot remember the name.)
I often went there because they had good food, free popcorn or snacks, and a decent selection of tap and canned beers.
Side story: At the bar, I often struggled with self-doubt before the trip, wondering whether I should be traveling. Can I cancel it now without losing too much cash? I would remind myself that it is okay for me to travel.
After a few drafts and bowls of popcorn, I had to get ready to climb aboard the California Zephyr.
California, here I come; a new Amtrak Adventure is underway!
My seat was behind the center stairwell on the train. I had a female seatmate from one of the Scandinavian countries who was visiting the USA. If I remember correctly, she was on her way to meet with her boyfriend, who met her in LA after visiting the Bay Area.
After the train left Chicago, I walked to the Sightseer Lounge car, found a seat, and started chatting with a Canadian gentleman.
While riding the rails, the dining car steward came through, and I decided to treat myself by making a dinner reservation. After a while, the dining car steward called to confirm my dinner reservation. Since I was in the Sightseer Lounge car, I didn’t have to walk far, as the dining car was right next to it.
When I got into the dining car, I was seated with three ladies: a couple from San Francisco and another solo traveler. After we sat down, I asked if they were all from the United States, and they looked at me and said, “Yes, but why?” I told them they were the first US citizens I’d spoken to on the train, aside from the staff. We had a nice chuckle, and it broke the ice. The City by the Bay ladies gave me some excellent tips and hints.
Later that year, I wanted more Amtrak Adventures.
A few things happened on my first long-distance Amtrak adventure; I fell in love with the views, the pace of train travel, and the people who made my trip fun. All of these made me fall in love with train travel.
After my first long-distance trip, I experienced withdrawal from train travel and craved more of it. I discovered Amtrak’s Midwest Corridor, which offered several day-trip destinations.
The furthest destination I could go in a day was St. Louis, MO; the closest was Milwaukee. I needed to learn a new skill: riding Metra. By the way, it is not hard.
Metra could take me to Chicago earlier than the Hiawatha, giving me time to grab coffee or breakfast and catch the early trains. Plus, Metra is cheaper.
Tuesday became my train day, and I rode a train on that day, or at least once a week, for years.
One big trip for the year wasn’t enough for me, so I booked another long journey to Washington, DC, this time. The trip was another coach trip. I took the Capitol Limited to DC, stayed the night, and took the Cardinal home.
Why am I telling you about my Amtrak Adventures?
Everyone Starts Somewhere: My First Steps into Travel
I’ve always been fascinated by the world—how big it is, how different people live, and what’s just waiting to be discovered. As a kid, I watched cooking shows, and one of my favorites was Yan Can Cook. His message stuck with me: If Yan can cook, you can too.
That idea became my travel philosophy as well. I’m not a fearless adventurer or elite globetrotter—I’m just a regular person who decided to try it. If I can travel, so can you.
I’ll be honest: when I first started traveling, I was nervous. Perhaps you’ve felt that way too—the jittery feeling in your stomach before a big trip, wondering if you packed the right items or booked the right train.
That anxiety almost prevented me from taking several trips. However, I’m glad I didn’t let it win. Fear and worry can hold you back from experiencing truly amazing adventures. While I completely understand and respect those who struggle with intense fear or anxiety, I want to encourage you: sometimes, simply showing up is the bravest thing you can do.
Are you ready?
This story marks just the beginning of my journey. I have made mistakes and learned through challenging experiences, but that’s all part of the process. Travel is not just about visiting new places; it’s a skill you develop over time. It teaches you patience, flexibility, and the ability to laugh at yourself when things don’t go as planned.
And maybe… this is your moment to begin your story.
The best way to become a better traveler is simple: start. Book the ticket, reserve the room, grab your bag, and climb onto that train. Experience is the best teacher. The more you travel, the more confident and capable you will become.
Remember this: your attitude is more important than your itinerary. Travel may not guarantee happiness, but it can be an excellent way to find it. If you approach your journey with curiosity, kindness, and a sense of wonder, you’ll be amazed at what you receive in return.
Ready to start your Amtrak journey? Click here to begin your research on riding Amtrak.
Safe Travels!
Kev
Do You Love Train Travel?
Want more insider Amtrak travel tips, route guides, and travel updates? Join my free Travels with Kev newsletter to get my Quick Reference Guide to Amtrak Long-Distance Trains, covering train equipment, dining options, and more. It comes out every Thursday!
It is a simple way to start planning smarter, smoother train trips.
If this guide helped you, you can also support my work through my Support Page or by joining me on Patreon. Your support helps keep Travels with Kev going, and paid Patreon members receive a postcard from my travels each month.
