I have experience with your exact kind of plan. Except, it was my mother, who had *never* been on an airplane.....she had a fear of flying her whole life that kept her from ever getting on a flight. When she was 69 years old she told me that she was going to overcome her fear and wanted to go to Italy. And so DH and I told her that if she could overcome that fear, we'd take her and her sister (my aunt), on the trip of a lifetime to Italy. My father had no interest and was too ill to have made the trip anyway. It was a trip my aunt never could have afforded.
Anyway, my Mom saw a hypnotherapist to overcome her fear....and it worked. We did get a back-up prescription of Xanax just in case, but she did amazingly well...flew from NJ to Rome and back, saw Rome, Tuscany, Florence, Venice and the Amalfi coast...two week trip. She hasn't stopped talking about the trip.

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We did get a medical
travel insurance policy for her. But she had no issues on the trip. Three years later at 73, we took her to France. Again, great trip, and she got to see where her Father fought in WWII.
I agree...with others, if you can afford premium plus (on United), or splurge for business class....this is the time I'd do it. We did this with my Mom for her first flights to Italy and back....and it made the whole experience a lot smoother for her (and it didn't suck for us either

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