The first route suggested is right on, did that last spring. Other Highway to peruse is 39 out of Kerrville. State Parks: Garner is the biggy, along the Frio, but will be booked up. Then Lost Maples State park, which is near the 337 Sister road I believe? It will also probably be booked up.
Food: Leaky, look for an Italian Restaurant, it just changed owners, but is still very good, just can't decide on pasta or pizza
Sorry, can't think of name at the moment, but its the only one, on west side of US 83 there.
Concan: About 20 miles south of Leaky is the area of Concan...not exactly a town, but several cabins/campgrounds along the Frio River south of Garner State Park. In Concan, look for "Neals" restaurant, very good, ate there several times last year.
Utopia: Place to get a piece of pie, restaurant is on a corner, east side (forgot name). Good pie, not so friendly folks however.
If for some reason he's in Bandara, OST Restaurant is the popular bike place, especially for breakfast. Also a good coffee shop just next door that opened up.
My wife and I spent a year there this past school year, Sabinal ISD...don't really miss the jobs, but the area was a lot of fun for a year.
Enjoy the Three Sisters, they were fun.
Scotchale