My wife came with (and still has) an '88 Superglide and we have ridden many thousands of miles together over the years. Had great fun and met lots of great people. A great way to travel and you can carry so much more stuff with two bikes.
Unfortunately, since a double hip replacement, (nothing to do with wrecking) she does not like to ride anymore. The Harley hasn't been out of the garage in two years because I do not like to ride it (It is lowered slightly for her and I make too many sparks). Trying to talk her into selling it.
Thinking of buying a larger, two up, touring machine. Rented a 1200GS a few years back in Spain and I loved it. Those expanding saddle bags are fantastic although you need a "Wide Load" sticker on the back.