Last weekend my wife bought a real bike to replace the so-called cruiser which should be called a parker. Living on the west (mountain) side of town real hills couldn't be avoided without driving. Well, all the hills that she was anxious about were mastered and a great time was had. Next step will be overcoming anxiety on downhills but I still remember when I suffered from that.
She got a flat-barred road bike (Giant FCR-3 I think) and put some 'cross tires on it and I think (I try to avoid that) this'll work out well.
1970s Royal Scot 3-Speed, 2005 Breezer Villager 7-Speed IGH
Sounds like you're in for some fun! Last November my wife went from No Bike, and ride-shy after falling twice a couple of years back, to entry-level 7-speed step-through town bike (Raleigh Ventura); within a few weeks she was joining me on my regular 5-mile climb, and this summer we toured together for a week in France. She still rides the brakes on the descents, but considering what she has accomplished I'm ready to cut her all the slack she wants on this.
Of course if she starts dropping me I hope she''ll return the favor...