Rookie Mistakes to Avoid on Your First Long-Distance Amtrak Ride

A first-time Amtrak passenger shares 5 tips to make the most of a 20-hour train trip.

Apr. 17, 2026 at 1:07pm

Got story updates? Submit your updates here. ›

A bold, geometric illustration in the Art Deco style, featuring sweeping gradients of warm colors and towering, forced perspectives of a train station or landscape, capturing the grand scale and romance of train travel without any literal depictions of people or text.The majestic scale and streamlined design of long-distance train travel evokes a sense of adventure and possibility.NYC Today

After booking a last-minute 20-hour Amtrak trip from Chicago to New York, a first-time long-distance train traveler shares the key mistakes she made that kept her from fully enjoying the journey, including not packing essential sleep items, relying too much on the train's water supply, missing the café car, wearing uncomfortable shoes, and sitting on the wrong side of the train for the best views.

Why it matters

With air travel facing ongoing disruptions, more passengers are turning to Amtrak for long-distance trips. This story provides practical advice for first-time Amtrak riders to help them have a more comfortable and memorable experience on extended train journeys.

The details

The author, Kristine Villarroel, booked a last-minute 20-hour Amtrak trip from Chicago to New York after canceling a flight. As a first-time long-distance train traveler, she made several rookie mistakes, including not packing a pillow, blanket, and earplugs for better sleep; relying too much on the train's small water fountains instead of bringing her own large water supply; missing the café car due to a route change; wearing uncomfortable heeled boots instead of slip-on shoes; and sitting on the wrong side of the train to see the scenic Hudson River views.

  • The 20-hour train trip took place in April 2026.
  • The author booked the trip with less than 48 hours before departure.

The players

Kristine Villarroel

A first-time long-distance Amtrak passenger who shared her experience and mistakes from a 20-hour train trip between Chicago and New York.

Amtrak

The national passenger railroad service that operates the long-distance train route the author took.

Got photos? Submit your photos here. ›

What they’re saying

“Next time, I'll make sure to bring a comfortable blanket, at least a neck pillow — if not a full-size pillow, as I saw fellow passengers using — some earplugs, and maybe invest in a better eye mask.”

— Kristine Villarroel, Amtrak Passenger

“An Amtrak spokesperson told Business Insider by email that the Lake Shore Limited train, which I was traveling aboard, splits into two separate sections, with one half featuring a café car and the other a first-class dining car.”

— Amtrak Spokesperson

What’s next

The author plans to apply the lessons learned from this trip to better prepare for her next long-distance Amtrak journey.

The takeaway

Taking a long-distance Amtrak train for the first time requires extra planning and preparation to ensure a comfortable and enjoyable experience. Packing essential sleep items, bringing a reliable water supply, familiarizing oneself with the train's layout and amenities, and choosing the optimal seating location can all help first-time riders make the most of an extended rail journey.