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Travel with an older person in the winter

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I'm posting this in the U.S. forum because that's probably where we'll end up, but we are not actually limited to that. My father, who is 85, and I will need to vacate his house for 10 days or so in the next month or two, due to construction. We'd like to go somewhere warm and/or interesting. He'd prefer not to fly, but flying is not completely out of the question. Anything over six hours is, and two is more like it. We may end up on either a cruise ship out of NYC (near where we live) or taking Amtrak to Florida because they're simple, but I thought I'd see if anyone had ideas.

He'd love something like a European river cruise, but he's simply not up to flying to Central Europe. Ireland is probably just doable, but the idea of hauling halfway across Europe overland or trying to hop across on short hauls has no appeal. Cruising to Europe is the same issue, because it's really tricky to do it both ways.. He's alert, but he tires quickly, and he uses a rollator or two canes. They're mostly for balance, and he can handle moderate stairs, but things like ladders aren't possible.

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