In classic boomer fashion, I have six siblings, but one of them — Mary, 25 months older — and I have always been a pack of two. That tight bond, forged during the decade we shared a childhood bedroom, has made us ideal travel buddies over the years. Now that we're in our 50s, though, Mary and I find ourselves strategizing about our ultimate destination, not just another trip we plan to take together. We may live 1,400 miles apart — Mary's in Houston with her family; I'm in L.A. with mine — but we've promised to move closer when we start the next chapter of our lives.

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We once dreamed about settling in a wine region of California, but soaring housing costs and a severe drought have made us consider other options. One possibility: the Texas Hill Country, a scenic, 14,000-square-mile expanse stretching west from Austin to the Mexico border. Though neither of us had ever explored it, we had listened to friends rave about the area's friendly and affordable small towns. So last fall we hit the road to check it out for ourselves. 

It's dusk by the time we head west on U.S. 290. Normally a pastoral and rolling four-lane route, this Friday evening its white lines are masked by blinding rain. Mary — the lifelong braver sis — valiantly steers us through the deluge. By 7:30 p.m. she has us ensconced before a fire at Fredericksburg's Crossroads Saloon and Steakhouse, where we sip wine, sample a delicious bison filet (a culinary first for us both) and eat off each other's plates as we plot tomorrow's route.

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After dinner, I take the wheel (it's the least a sister could do) and shuttle us five miles east of town to our base of operations for the weekend: Settlers Crossing B&B. On 35 acres populated by deer, sheep and donkeys, the escape features seven historic homes dating from the late 1700s. Mary and I settle into the Indiana House, an 1849 cabin moved here in the 1980s. Learning there are two bedrooms, Mary exults: "A night's sleep free of your snoring!"

Saturday morning we venture four miles down Ranch Road 1376 to Luckenbach, Texas, immortalized by the Waylon Jennings song. Today the burg that promised to get us "back to the basics of love" is little more than a ghost town, its post office converted to a gift shop and bar. We grab souvenir coffee mugs and head for the 19th-century German-immigrant settlement of Boerne; like Fredericksburg, it boasts a picturesque main street dotted with boutiques and cafes. Because a perk of traveling with your sister is never being shy about your appetite, Mary and I are soon lunching at Brantley's Bistro. Among its locally sourced meats and produce are fresh tomatoes to die for from Marfa, five hours west of here.