- Cali O'Connor bought an Amtrak USA Rail Pass to get from Boston to Napa two summers ago.
- She spent 96 hours on trains and stopped along the way in three different cities.
This as-told-to essay is based on a conversation with Cali O'Connor, a 35-year-old freelancer from Boston. The following has been edited for length and clarity.
I took a 96-hour train ride from Boston, Massachusetts, to Napa, California. I've spent a lot of time traveling internationally, but I haven't seen much of the United States, so when I had to travel to a wedding in Napa two summers ago, I figured I'd give Amtrak a go.
A plane would've taken about six hours and cost around $300 (plus the cost of a rental car to drive from San Francisco International Airport to Napa Valley), but I chose Amtrak for financial reasons and just to take an adventure.
I purchased the USA Rail Pass, which usually costs $499 but was on sale for $299 that June, three months before my trip. Here's what the journey was like.
Using the pass, I was entitled to 10 rides within 45 days
I ended up using six of the rides. I started my journey in Boston, then stopped in Milwaukee, Wisconsin; Whitefish, Montana; and Seattle, Washington, before getting to my destination of Napa.
I got off the train at each of the stops and spent time in those places. With all my stops and the travel time, it took about 10 days to get to California.
The first leg of the trip was from Boston to Milwaukee, which took about 27 hours. It took another 30 hours to get from Milwaukee to Whitefish, then 14 hours from Whitefish to Seattle. The last leg, Seattle to Napa, was 25 hours.
The views from Whitefish westward were incredible, though a lot of the traveling happened at night, so it was difficult to see everything. I did try to see the sunrise each morning.
The 30-hour leg was the longest, but it was surprisingly manageable. By the time I got to the 14-hour leg, it felt short.
I had a great time and I didn't have a bed
With the rail pass, you get a coach seat, which means you're not given an overnight cabin or a designated area to sleep.
Looking back, I don't wish I would've upgraded to a business-class seat — the price difference just isn't worth the extra comfort.
Luckily, no one ever sat next to me on the overnight portions (probably because they wanted space themselves), so I was able to curl into a ball and sleep. That might sound awful to some people, but I'm used to budget traveling in places like hostels, and it was worth it to be on the train during the day and see the beautiful scenery passing by my window.
It was a wonderful adventure
In Milwaukee, I met up with a friend who lives there. The city surprised me with how fun it was. One day we kayaked on the Milwaukee River; there were people floating along next to us, drinking beers and playing music. It was just such a good time.
When I estimated everything, I found that taking the train was the most cost-effective way of traveling to California, especially since I was going to Mexico afterward and not back to Boston.
In the cities I stopped in, I used credit-card points to book hotels, so I didn't spend anything out of pocket.
I also brought a cooler with me that I restocked at each stop. I'd go to Trader Joe's to get snacks and drinks, and I even brought a collapsible bowl to make my favorite salad while on the train. There were food options on all the trains, and the prices weren't that bad, but they weren't the healthiest choices. Plus, it was another way to save money.
There were a few small moments when I regretted my decision
Those moments were temporary — like when a woman was watching YouTube videos without headphones on, or when I had to go all the way downstairs to brush my teeth in a shared bathroom. The train was also kept pretty cold, and I wish I'd brought a bigger blanket with me. But overall, I had a blast.
I had so much fun that I'm hoping to do it again. I want to take a different route and see some new cities. I even shared my journey on TikTok and was so happy to see responses from people who were interested in doing it themselves.
Now I help other people schedule "career breaks" through traveling. I tell my clients if you're comfortable being a little bit uncomfortable, the Amtrak USA Rail Pass is a really cool, cost-effective way to see the country.