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I met a woman who was in her mid 80's on a cruise ship a few years ago that was doing this. I sat and talked with her a bit one day, she was close to full timing it on cruise ships, spending over 280 days per year on cruise ships (mostly Princess Lines), in between she would go visit her daughters. She had spent the previous 6 weeks on the same 7 day loop cruise, and was about to depart that ship to go spend the holidays with one of her daughters. She told me that the cruise staff were very attentive of the needs of their regular customers such as herself, that the medical team would check in with her to make sure her health was ok from time to time, etc. and of course by cruising that much she received all sorts of perks, free upgrades, and discounts.
As to the Hobo side of the conversation, I had a great uncle who did the also rode the rails during the depression, he was born in the late 1890's so was about 30 years old when the great depression began, he and my grand father worked on various work projects in the great depression, mostly building water towers in Texas and the western states, though my grand father who served in the Navy in the late 1920's also worked on building Hoover dam.
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2002 Safari Trek 2830 on P32 Chassis with 8.1L w/ 400 watts solar 420Ah LiFePo4
2017 Jeep Cherokee Overland & 2007 Toyota Yaris TOADs with Even Brake,
Demco Commander tow bar and Blue Ox / Roadmaster base plates
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