USA Rail n Road Trips

Embarking on a trip from Boston to Seattle via the Amtrak.

In March, there was an Amtrak sale for the USA Rail pass for $399.00, so I bought it. Not on a whim — I had been thinking about it for months and saw the sale and felt like the timing was finally right.

A few things to know about the rail pass…

1. Once you purchase the pass, you have 4 months to use it.
2. There are ten segments that come with the pass that can be used however you want to use them, except for a regular commute.
3. Once you start booking your travel, you have 30 days to book all 10 segments of your journey. Any train switch counts as one segments.
4. The pass is for coach seating only, you can upgrade to business class or a sleeper car but would have to pay the difference.
5. There are a limited number of rail passes allowed per train, so you either have to plan each segment in advance or be incredibly flexible with your plans.

The first segment on my trip was on the NE Regional Train from RTE 128 in Massachusetts to Penn Station in NYC. I stayed at The New Yorker Wyndham Hotel because it was close to the station (I needed a quite space to do some work) and maximized my night by eating amazing food, seeing a Broadway show – A Strange Loop – and exploring Times Square night life.

The night began with my friend and I dining at Il Buco, a Michelin star restaurant with Italian and Iberian inspired cuisine. It has copper pots and pans hanging from the ceiling with wooden floors and tables. We ate fresh octopus that tasted so good it brought me back to the streets of Sicily. For an entrée, I had a spinach risotto that ignited all my tastebuds. The best part was the food was so fresh that I left feeling energized and not like a potato that needed to be rolled to the nearest couch. It was the perfect start to our lovely, jam-packed evening.

A Strange Loop was next on the itinerary and utterly amazing. It is a musical written by Michael R. Jackson, about a black queer man trying to write a musical. There are only 7 characters in the whole play, the protagonist and 6 of his emotions. It is jaw-dropping and harsh one moment then sensitive and heartfelt the next. I would highly recommend it.

Jimmy’s Corner was the next stop. It is a dive bar in the middle of Times Square – if you don’t know about it, you will miss it. This bar is probably the only place in New York where you can get a drink for $5 or less. It is small yet charming, with the history of Jimmy’s life in pictures on the walls. Jimmy passed away due to COVID; however, his son pledged to keep his father’s bar alive and operating as it has the past 50 years.

After Jimmy’s corner, I was at the mercy of my friend, a native New-Yorker, who took me to a bar in the subway. Instead of going left and through the turn style, we went right into a sleek bar with high-top tables and a loungey vibe. There were a variety of creative, fruity drinks here, and though it was not Jimmy’s Corner cheap, it was also not outrageously priced.

Times Square was alight and bustling when we left around one in the morning. Feeding off of the city’s energy, we ate some $1 pizza that was sub-par but truly hit the spot!