Key West and next steps
So, Key West, did it turn out to be better than my first impressions? No. It did not. Key West is a tourist trap. If you have been to Niagara Falls, the Las Vegas strip, Times Square in NYC, most of Venice, or any spectacularly popular old town or scenic area in the world, you've been to Key West. The whole town is essentially mediocre bars playing
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Central Texas: https://www.amazon.com/gp/product/B004USHMI6
Texas Hill Country: https://www.amazon.com/gp/product/B004USHLB4
The author is a friend of mine, and his book are less about tourism and more about history. He'll take you to old ghost towns, important places in history, non-important places in history, and other spots. He also has information about local food, sights to see as well as CAMPING areas.
The downside to the book is they're about ten years old, so some of his suggestions are gone, the camping rules may have changed, and many of the ghost towns are really just spots on the roads.
But for history of where you're going, and eating local, these books are still the gold standard for me.
In the replies, I'll also give you a few suggested routes I know of through the Hill Country/Central/South Texas. Suggestions, of course, not STICK TO THIS. :)
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Suggested Routes:
Houston to Austin
1) https://goo.gl/maps/6gJZPHfdR7BNRyiy8
This route runs across the extreme southern edge of Czech Texas. Suggested stops are Weikel's in La Grange for pastries, and downtown Bastrop which is hugely historic in Central Texas history as well as looking pretty rustic. There's a large state park complex between Smithville and Bastrop (Bastrop State Park and Beuscher State Park) which allows tent camping. The trip through Webberville is lovely and quiet, and will take you right past one of the places I lived in Austin.
2) https://goo.gl/maps/vkf9z695VB9q764h6
Highlights here are Royer's Round Top Cafe in Round Top (a lovely town on it's own with an outdoor museum of old pioneer houses and the old county courthouse when Round Top was the County Seat), a beautiful always-open Czech Church in Serbin and the oldest black community in Travis County, Littig. There's a portion of this route on US 290, which is very heavily travelled, but much of the road is paralleled by the original older highway alignment, which I'd recommend. I just couldn't put it on the map without wasting all my available waypoints just keeping the route on the road. You should be able to see the old highway on anymap, just to the north of US 290. Bastrop and Beuscher State Parks are still within distance of this route.
Houston to San Antonio
1) https://goo.gl/maps/o6t39PqxDakuoKcf9
A nice flat ride from Houston to San Antonio. The Shiner brewery is on the way, where you can check out their tasting room and see beer being made (Shiner is probably Central Texas' most loved beer). Gonzales (home of the much misunderstood "Come and Take It" canon) and Seguin are older Spanish towns. Gonzales maintains a lot of it's Spanish origins, Seguin, not so much. The trip through Farm to Market 78 used to be the Upper Seguin Road and goes from a larger FM highway to a Great Big Road. Just to the south is the much smaller and quieter Lower Seguin Road.
2) https://goo.gl/maps/sq7cRYKLC6iRjDC79
This route is much closer to IH-10, and while it never quite goes on IH-10, it's always nearby. It's often paralleled by US 90 which is a MUCH quieter route, since only local traffic uses it. There are a few times, though, where you will need to bike on the frontage road for IH-10. Sites to see here are the Big Czech Church in Praha and...well...the smaller towns out here for sure. City Market in Flatonia is good BBQ, but it's the mushy kind you probably wouldn't like. :)
San Antonio to Austin (and vice versa)
1) https://goo.gl/maps/wUtnpUTM4LHiJuyr5
The trip I'd take to visit my parents and a road I'm intimately familiar with. IH-35 is always nearby, but this route (the old Stagecoach route between Austin and San Antonio) takes you through all the old towns on the stagecoach route. Point of interest: Old Town Buda, looking much like it did 100 years ago, Kyle which is only now starting to grow bigger than its "cattle railroad town" origins. San Marcos (another town where I used to live) is the Big University out here. Lockhart, considered the heart of Texas BBQ is a nearby sidetrip (I prefer Black of the three feudin' BBQ joints). Gruene still maintains it's 1880s look, but is a complete tourist trap now. New Braunfels has maintained its German heritage in a less exploity way than Fredericksburg. One of my fave German restaurants is there, The Alpine Haus. The segment on Nacogdoches Street and Old Nacogdoches Road is on one of the oldest continually used roads in North America (El Camino Real, but used centuries earlier by Native Americans). Comal on the corner of FM 482/Old NAcogdoches Road is one of the few Ghost Towns out here that still has all it's buildings up, at least the last time I was out there.
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These two trips are trips I made specifically for going towards my parents house, while still going through the Hill Country. From Kendalia to San Antonio, they're the same route, but there's a northern and southern route out of Austin. On the northern route, you'll be on the larger, but quiet US 290 through to Dripping Springs. A neat thing about Dripping Springs are the buildings in the old town area, which are all of this neat colored rock. Blanco is another of those "Still looks like 1880s" towns. Blanco River State Park is on the south end of town on the Guadalupe River.
On the southern route, Driftwood is a total ghost town with just a post office left and some older buildings and dwellings. Wimberely is where all the arts and crafters and hippies went when Austin gentrified in the 2000s. Fischer is another old ghost town with one of the few nine-pin German bowling alleys left in Texas. To the south is Canyon Lake which may have some camping possibilities.
From Kendalia south: Kendalia is another small little German ghost town. I couldn't route you through Edge Falls road south of here because of Google Maps' waypoint limitations, but take it if you can. You'll be biking through open range in some areas, and there's a wonderful view of the creek from a high bridge. The creek is often dry, but it's a great view wet or dry. Guadalupe State Park is nearby, which I believe allows tent camping. Bergheim is another Ghost town, with just a general store (and that was closed last time I was through there). Leon Springs is now a larger urban area now that San Antonio has grown out here. IT does have some servicable BBQ from Rudy's downtown, but right downtown in Max Aue's Home and Hotel (just south of Rudy's). That home is one of the first ever built in the Hill Country and is used as Rudy's HQ. It's been there since the 1840s. The Hotel from the 1880s. Tour ends in Helotes, another small town losing it's small town flavor as San Antonio grows out here.
That should get you started if you want to head into Central Texas. I could give you Hill Country routes galore, although the Richard Zelade books I suggested will probably have most of the same tours. Heading out of Texas to the west, I have a few trips you may like, but I'll save those for when/if you decide to head that way....
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