We travel by bus from Bangor, ME to Boston quite frequently, to fly out of Logan. It's about a 4 hour bus trip and I don't mind it at all. The bus line (Concord Coach) has comfortable seats, wifi, they show movies, and give you free bottled water and pretzels. What's not to love?
When we lived in Syracuse, NY, we took Amtrak to NOLA to visit my sister over Mardi Gras. Train went from Syracuse to Chicago, then south to New Orleans. We got on the train at about 1am, slept several hours (in our seats- it was reasonably comfortable) and had breakfast in the dining car somewhere around Cleveland. Train got into Chicago around 1pm, so we walked around a bit (pretty darned cold in Feb) and took The City of New Orleans, departing around 6pm. Slept in our seats that night- although I remember waking up in Memphis, absolutely mesmerized as we were passing by a fairgrounds- it was foggy and the lights were on and it was mystical! The train ran late as there was a freak ice storm and we could only travel something like 20mph through much of Mississippi. Imagine- we came from Syracuse only to be confoozled by winter weather in Mississippi!!
On our return trip, we traveled up the east coast. It was very cool taking the train across Lake Ponchatrain, in NOLA... the tracks are only about 5 feet above the water or something like that, so you feel like you are skimming across the lake. There wasn't anything very exciting on this part of the journey, mostly just traveling through the shabbier parts of major cities. It was interesting in the south to see how different the buildings/houses and plant life is from that in the north. We spent a lot of time talking to other passengers in the club car (but too smoky to stay too long; yes, it was that long ago that people could smoke on the train). We changed trains in NYC for one that went north to Albany and then west back to Syracuse. It must have been a pretty good trip; I remember a lot of the details, and this happened back in 1988!
I've also taken the train from Boston to NYC several times, and from Boston to DC. The train to DC is convenient; you leave Boston around midnight and arrive in DC for breakfast. No time to be bored, plenty of time to sleep and arrive ready to play tourist! This summer, IF we are allowed to travel easily, we are planning to fly BOS-Denver and then fly home from Salt Lake City to Boston. To go from Denver to SLC, there is a 15 hour train trip through the Rockies that we are considering. I am always the driver in the family (I get motion sick on everything except trains) so taking the train through the mountains will let me enjoy the scenery instead of making the trip with my hands white-knuckled on the steering wheel, my eyes glued to the road instead of taking in the majestic mountains!