I’m from Toronto. Twenty years ago, I had some business in SF, and I scheduled it for the same time as MacWorld SF.
My partner and I flew to Chicago, where we caught the California Zephyr to Oakland. We had a small cabin, but it was great. Waking up at 6am in Denver was astounding, as was that entire day. SLC at 1am was surreal. And crossing the Sierra Nevadas was unforgettable.
We hung out in SF for a few days, went to MacWorld, and I had a few meetings. Then back to Oakland for the Coast Starlight to Portland. Now we had a bigger cabin with its own bathroom and shower. Bliss!
From Portland, we took the Empire Builder across the top of the US back to Chicago, from whence we flew back to “HogTown.”
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Random memories:
1. Massively more comfortable than flying. You don’t have to go to a lot of trouble to get aisle seats and what-not just to avoid feeling like you’re an Amazon package being shipped somewhere.
2. You actually SEE the country. It’s amazing to fly over mountains and cities, but rolling past that scenery is so much better, especially when you can view it from the gondola instead of leaning past the passenger with the window seat to peer through a porthole.
3. Way more social. Kids were meeting each other and playing video games in the theatre car. We played cards with a couple we met. The stewards facilitate this by seating you at meals with other couples. If you’re a single, they make up different tables of four singles each meal to help you meet fellow travellers.
4. Unplanned interruptions are different on a train. There was an avalanche/rockfall ahead of us in the Cascades, the train pulled onto a siding and we watched the “Snowball,” a work train, go by with its flatbed, crane, and hefty workfolks waving to us. A few hours later, back it came and we could proceed.
5. Way less stressful in every dimension I can think of, compared to modern aviation. It’s part of the vacation, not a way to get to the vacation.
Summary: Train travel, if you spring for a cabin, is land cruising without the buffets and casinos.