Hello Reader,
I want to thank all of you who sent birthday wishes last week. If you didn't, that is okay too. My niece and I made it home on Thursday afternoon. She was glad to see her grandparents, and they were glad to see her as well. I'll share a little more about that later.
6 Lessons from 200,000+ Miles of Travel
After more than 200,000 miles of travel, I have learned that the best travelers are not always those who plan every detail perfectly.
They are the ones who can adapt to change.
I have traveled by air and by land, though not yet by sea, and a few lessons keep showing up no matter how I travel. Whether I am catching a train from Milwaukee, flying out of O’Hare, connecting in Chicago, or traveling with family, the same basic ideas hold.
These lessons are not meant to scare you away from traveling. They are meant to help you enjoy it more. The more flexible you are, the less likely a single delay, mistake, or rainy day is to ruin the entire trip.
1. Travel involves trade-offs
Travel does not always go as planned.
Sometimes, when traveling, we have to make compromises. That is not always fun, but it is part of the deal.
For example, if you want to take the train from Omaha to California, you may have to board the California Zephyr near midnight, which is not ideal for most people. But if the train passed through Omaha earlier, you might miss some of the best scenery farther west.
That is one of the realities of train travel. Sometimes you board early in the morning. Sometimes you arrive late at night. Sometimes the schedule is not built around how you would prefer to sleep. That can be because those sacrifices mean better transfers and the views we want.
Flying has trade-offs, too. A cheaper flight might depart earlier than you want. A better connection may cost more. A more convenient airport might offer fewer options. A longer layover may feel annoying, but it might also save your trip if something runs late.
Every choice involves a trade-off.
Once you accept that up front, the trip becomes easier to manage and usually more enjoyable.
This goes beyond transportation, too. On my last trip with my niece, I had ideas about how the trip would go, but she had different ones.
Was she wrong? No.
Was I wrong? No.
But things did not go as I had pictured them, and that is okay. Sometimes the best we can do is change our attitude, let go of what we cannot control, and enjoy the trip that is actually unfolding.
2. Always have a Plan B
Having a backup plan does not have to be difficult or complicated.
You do not need a giant spreadsheet or a binder full of alternate routes. Sometimes, a backup plan is simply knowing your next option if something goes wrong.
When I was flying out of O’Hare to visit my sister, I often took Metra’s North Central Service to the airport. Usually, three trains worked for me: Plan A, Plan B, and Plan C.
Most of the time, I took Plan B.
Plan A got me there very early. Plan C got me there a little sooner than just in time. Plan B was balanced. It gave me enough time to get through the airport, grab some food, and maybe enjoy an airport beer without sitting around for hours.
Once, something went wrong with the train I was on. We were dropped off at the next stop, and the next scheduled train picked us up.
My Plan B became Plan C. If I had gone with Plan C and this had happened, I would probably have had to reschedule my flights.
Because I had built-in breathing room, the problem did not turn into a disaster. I still made my flight, even though I had less buffer time than I wanted.
That is the purpose of a backup plan. It prevents a problem from becoming a crisis.
Sometimes, Plan B is taking the next train. Sometimes it is changing your connection. Sometimes it is staying overnight somewhere you did not plan to. And sometimes, sadly, Plan B is canceling the trip altogether.
The weather can change your plans. Illness can change your plans. A mechanical issue, a delay, a family need, or an “act of God” can change them.
Sunny Florida is not always sunny. A perfect connection can fade. A great daily plan can fall apart because you wake up tired or the weather does not cooperate.
Having more than one option does not guarantee that everything will work out, but it gives you a better chance of staying calm and making the right decision.
3. Give your connections breathing room
Just-in-time transfers sound smart in theory.
You get from point A to point B with no wasted time. You arrive, walk to your next gate or platform, board, and keep moving.
That sounds great until something goes wrong.
Most people do not enjoy rushing to catch their next flight or train, and for good reason. When you are stressed and rushing, you do not function as well. You do not hear clearly and do not process information as effectively as you normally would. You miss signs, misunderstand directions, and make mistakes.
I am not saying this as a theory. I am saying it because I have been that traveler.
Travel already has enough moving parts. Tight connections make even small problems feel larger.
If something goes wrong, such as a delay, a gate change, confusion about where to go, or a long walk between terminals or platforms, a tight connection can unravel quickly.
Then you are not just dealing with a missed train or flight. You may need to rebook, cancel plans, call hotels, adjust your arrival arrangements, and reorganize the rest of your trip.
One small problem can trigger a cascade of issues.
Sometimes, tight connections are unavoidable. On my last cross-country trip, my train was late, but I still had enough time to disembark from the Southwest Chief in Chicago, enter the station, and walk down the next platform to board my connecting train, the Floridian.
Normally, that is supposed to be about a three-hour layover. Because of a delay, most of that cushion was lost.
That was out of my control. The trip was well planned, but things happen.
There is a difference between a tight connection caused by a delay and one you create on purpose because you like to cut things close.
When you build breathing room into your schedule, you are not just being cautious. You are protecting your entire trip.
That extra time may let you grab food, use the restroom, find the right platform, ask a question, or handle a delay without panicking.
You can use Plan B when needed, and you get to take a breath instead of running down the platform.
4. Own your part of the trip
One of the hardest lessons of travel is realizing that not every problem is someone else’s fault.
Sometimes we misread a schedule. Sometimes we cut things too close. Sometimes we book the wrong date, misunderstand a rule, forget a detail, or assume something will work without verifying it.
Over the years, I have done all of those, which is how I compiled that list.
I once watched a train pull in and then leave while I was still trying to pay for parking. That was not Amtrak’s fault. That was not the parking machine’s fault. That one was on me. It became more than a $10 parking mistake.
I have messed up bookings and had to call Amtrak. I have had holds placed on my debit card because of a mistake with a hotel reservation. I have made small mistakes that have created extra stress for myself.
It happens.
When it does, the best you can do is admit it, fix what you can, move on, and learn to do better next time.
That does not mean companies never make mistakes. They do. Trains are delayed. Flights are canceled. Apps fail. Hotels overbook. Staff members may give incorrect information.
But before blaming the person in front of you, it helps to pause and ask, “What part of this is mine?”
From someone who has worked in customer service, I can say this: if someone is kind and admits they made a mistake, it is usually easier to help them. Even if it is not your fault, blaming the person helping you for something they did not cause rarely improves the situation.
This also means listening before speaking.
That can be hard when you are stressed, tired, hungry, or embarrassed. But if someone is trying to help you, give them a chance to explain your options. There were times when what people wanted was exactly what I said I could do for them, but they did not hear me out.
If someone helps you plan your trip, take the opportunity to engage with them. Ask questions, take notes, and review your itinerary. Know where you are going, when you are leaving, where you are connecting, and what you need to bring.
The day of departure is not the best time to sort out details that could have been handled weeks earlier, when stress levels were lower and more options were available. If you wanted to make changes, you could, but the day of departure is not the time.
Being responsible for your own trip does not mean you have to know everything.
It means you are willing to learn.
5. Leave room in your daily plans
I have seen people account for every minute of their trip.
That can work until it no longer works.
If one thing goes wrong, the whole day feels ruined because there is no room for any adjustment.
When I travel, I often batch activities rather than scheduling every single thing for a specific time. I may group ideas by area, day, or mood, but I try not to lock everything in unless I have to.
For example, I might plan to visit a brewery or two one day and hike the next. If Monday is supposed to be the hiking day, but it rains, I can swap the days.
Sometimes the weather sets the tone.
Sometimes your body does.
Sometimes, an activity you thought would take an hour takes three. Sometimes you find a great coffee shop, fall into a great conversation at a brewery, get a local recommendation you want to explore, or decide to stay longer than planned.
Those unplanned moments can become the highlight of the trip.
The older I get, the more I realize I need to plan for my current body, not the 26-year-old body my brain still thinks I have.
That does not mean I cannot have full travel days. It means I need to be honest about rest, food, walking, weather, and energy.
This matters even more when traveling with others. Kids, older adults, first-time travelers, and even experienced travelers can hit a wall. A plan that looks great on paper may be too much in practice.
Leaving room in your daily plans gives you permission to adjust without feeling like you've failed.
A trip does not need to be packed to be worthwhile.
6. Manage your expectations
How you approach a trip matters as much as how you plan it.
If you start a trip thinking, “Everything must go exactly as I pictured it,” you set yourself up for frustration.
Instead, I try to think, “Let’s see what this adventure brings.”
That is not pessimism; it is realism, with hope for the best trip I can create.
You are traveling by train, plane, and bus, and on roads you do not control. You are staying in accommodations operated by others. You are interacting with staff members who have their own rules, schedules, workloads, and bad days.
Things will not always match your ideal.
The roomette you wanted might not be available. A train might be delayed. The café car might run out of something you wanted. A hotel room might not be ready early. An attendant may do things differently from what you expected. The weather might ruin your hiking plans.
That does not mean the trip is a bad one.
It means the trip is real.
Here is what I have discovered: when you let go of perfectionism, travel gets easier.
You notice more. You adapt faster. You are in a better mood because you are no longer constantly comparing reality to the perfect trip you imagined.
You might discover a town you had not planned to visit. You might have a conversation in the dining car that becomes the highlight of the trip. You might enjoy a delay more than expected because it gives you permission to slow down.
I still make mistakes on trips, and things still go wrong. I have 800+ trips under my belt, and that has not changed.
But I stopped expecting my trips to go as planned.
The moment I accepted that travel rules are not mine, schedules are not built around me, and attendants are doing their jobs the way management says, not the way I do, everything became easier.
Final thought
When we start traveling, we often put a lot of pressure on ourselves to get everything right.
That is not fair.
If you are new to travel or returning to it after a while, you will make mistakes. I have taken many trips and still make mistakes from time to time.
If you do not have experience right now, that is okay, and sometimes it is better. This is your time to learn.
You may book the wrong thing, cut a connection too close, pack something you do not need, forget something you do need, misread a schedule, or have a day that does not go as planned.
That does not mean you are bad at traveling.
It means you are learning.
The goal is not to travel perfectly. It is to learn, adjust, keep going, and improve next time.
Build in breathing room. Have a Plan B. Hold your plans loosely. Own your part of the trip. Be kind to those who help you. And remember that a trip does not have to go exactly as planned to be worth taking.
Sometimes the best travel stories come from the parts you never saw coming.
What Is Kev Up To?
Thursday was my second ride on the Borealis. The first time was in the Horizon cars; this time, in the Superliner Coach Cars.
The day began with a scheduling quirk. Track work meant the City of New Orleans left an hour and a half earlier than usual, so even though we rolled in a little late, we still made it to Chicago ahead of schedule. We could have caught an earlier Hiawatha home, but it would have been a rush — and with a kid and luggage in tow, a relaxed layover beats a tight connection every time.
Kev's Tip: If you're arriving on a sleeper and connecting to another Amtrak train, you can use the Metropolitan Lounge during your layover — luggage storage included. At least in Chicago, I thought that had changed, or they had rolled back some rules. We dropped off our bags and explored the station with our hands free.
Now, about my travel companion. Grandma had loaded Mack's backpack with enough activities for a trip around the world — so many that it became too heavy for her to want to haul. Funny thing is, she barely touched any of it. Turns out the train was the activity.
What I loved most was watching her grow braver as the miles added up. Early on, she was nervous about walking between cars. By the time we boarded the Borealis, she was leading the way.
One quick note for the points-watchers: Amtrak Guest Rewards points are posting faster than before. It used to take about a week; this time, the points were in my account the day after I got home. One trip doesn't make a trend, but I'll take it.
Thank You!
Thanks to Rebecca M and Dennis K for hitting the green tip button last week. I appreciate it.
June is my birthday month, and for no particular reason, I'm offering you 49% off your first month on Patreon. If you join, you'll receive a postcard from me, and you can cancel at any time. Use code 15CE5. The older I get, the bigger that discount gets!
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Until Next Week!
Safe travels & Happy Planning,
Kev Monteith
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