I used to read the Smithsonian magazine and they always had these great-sounding trips listed in the back pages. The trips were sponsored by the museum/magazine and sounded really interesting. Also, maybe some of the small cruise ships would be good. I've seen listings for Society Cruises that sound awesome, especially for older folks. Lots of lectures related to where you're traveling, interesting people on board and great destinations. I vote for a cruise to the Galapagos Islands on one of the small ships, not a big cruise line. With a cruise, your mom can see the entire itinerary before she leaves home, and if she wants, once you get on board, she can plan out where she'll eat every meal. Once she's all scheduled, hopefully she can kick back and enjoy the scenery.
I've got the same issues with my GF, but she's not a joiner.
One thing that really helps the anxiousness is to make sure you pre-checkin for flights and have your boarding pass printed in advance. Also if you can get by with carry on only. In general minimize time in the airport, which can be an anxiety-inducing environment.
One thing I did with my dad, and may well try with the GF, is to call in advance for handicap treatment. Put her in a wheel chair, they meet you at the entrance and whiz you around security, pre-board, all that. They have a special lounge, too.
If anyone has a MasterCard platinum, you can use the first class lounge, even if you're in coach. Virgin's first class lounge is a vacation in and of itself.
Another thing that would be great, but I haven't done yet, is to UPS your bags in advance, and travel with no encumbrances.
I know our local NPR affiliate always has these awesome winter trips/cruises that they offer, like a tour of European markets and museums last year, or this year a cruise around the Southeast Pacific (Australia, NZ, and Fiji).
JANSA is offering a tour of England to its members in the summer of 2009, and you still have a few months to become a member.
Harvard does very cool-sounding trips for alumni -- like cruises to Greece with a Classics professor, who gives lectures on the area. I've always thought they sounded like fun, and I hate packaged travel. (And that might be a bit less weird than traveling with undergrads, at least for your mom.)
I get the impression from the website that they at least try to limit it to alum, but it might be worth calling and asking (or if you or your family has a connection, that'd work, too!). I would also assume other big colleges have similar trips?
Thanks y'all -- I knew you'd help me out. I was thinking about the JASNA tour, but I'm really the only Austen nut, and JASNA would be a pretty intense helping of Jane. (occiblu, muddgirl? Austen-fest 2009?)
The Harvard tours are awesome. None of us went to Harvard, though, except my uncle (mom's brother), who wouldn't be going, but maybe he can get us in. Our colleges are New England Conservatory (mom), UNH and BU (dad, deceased), Wesleyan (me), UVA (sis), Bowdoin (sis). I'll try to see if any of those colleges have trips.