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The Texas Hill Country is the southernmost American Viticultural Area (grape-growing region) and one of the biggest.
While it is certainly possible to drive it yourself, why not farm out the shuttling to a professional? Why not live every day like it's a bachelorette party?
There are two accessible wine trails commonly begun from San Antonio, the Dripping Springs path and the Fredericksburg path. Most tours involve two to four wineries. Costs and inclusions vary. Typically these tour prices don't include gratuity and taxes, so be aware. Specifics below.
Elegant Tours is probably the most customizable tour option, with options for wine, liquor and beer, as well as varying degrees of food ingestion.
Cottonwood Wine Tours does not require that you fill out a tour group yourself and will pick you up and drop you off for no additional cost if you live inside 410. Tours range from $65 to $205 depending on your commitment to the task at hand.
San Antonio Detours runs a Hill Country Tour that takes you to two wineries. It's a private tour, so presumably the more drinkers you have, the lower the cost.
San Antonio Wine Tours is among the best deals. If you have at least four friends, you can get a half-day for $89 per person. That gets you two locations.
Discover Texas Wine will take you to either Dripping Springs or towards Fredericksburg and Hye to the east. Half day is $110, and a whole day is $135. You can pick your stops, even.
Majesty Wine Tours offers a dizzying array of tour options from $65 to $225.
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