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  1. What Is a Mailboat? Working Postal Routes You Can Ride in 2026
  2. Winding Road Wine Tours

    Winding Road Wine Tours

    5.0 • 54 reviews
    Spring Branch, TX

    Winding Road Wine Tours creates easygoing, all-inclusive adventures through the Texas Hill Country. Founded by Texas native Richard and Irish transplant Meghan, this Gruene-based team pairs local knowledge with genuine hospitality...

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    Book Winding Road Wine Tours

    Addon image

    Private Johnson City Wine Tour from Austin & San Antonio

    Explore the quieter end of Texas wine country with your own shuttle and host

    $238.50person
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    Private Fredericksburg Wine Tour on the 290 Wine Road

    Your own shuttle, a local host and a tasting day shaped around your tastes

    $254.40person
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    Private Hill Country Wine Tour in Driftwood, TX

    Make the tasting route your own while a local host handles the driving

    $238.50person
    Addon image

    Private Custom Wine Tour from Austin & San Antonio

    Shape a Hill Country day around your tastes, with a local host-driver at the wheel

    $106
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    Private Custom Wine & Brewery Tour from Austin & San Antonio

    Shape your Hill Country day around the stops you love

    $132.50
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    Private Custom Wine, Beer & Spirits Tour in Fredericksburg

    Build a tasting day around your tastes and leave the driving to a local host

    From$201person
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    Private Fredericksburg Wine Tour & Main Street Lunch

    Enjoy wine country and village browsing without taking the wheel

    From$185person
    Addon image

    Private Fredericksburg Wine Tour on the 290 Wine Road

    Leave the driving to a local host and enjoy Fredericksburg's wine country

    From$201person
    Addon image

    Private Custom Johnson City Wine, Beer & Spirits Tour

    Build a tasting day around your own mix of wine, craft beer, and Texas spirits

    From$185person
    Addon image

    Private Wine Tour & Village Lunch in Johnson City, TX

    Pair Hill Country wine tastings with a relaxed small-town lunch break

    From$185person
    Addon image

    Private Johnson City Wine Tour on the 290 Wine Road

    Let a local host handle the driving while you explore the quieter side of Texas wine country

    From$185person
    Addon image

    Private Custom Wine, Beer & Spirits Tour in Driftwood

    Mix your favorite pours into a relaxed Hill Country day without doing the driving

    From$185person
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    Hill Country Wine & Village Tour

    Taste Driftwood wines with a relaxed lunch stop in Wimberley or at Salt Lick BBQ

    From$169person
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    Driftwood 3-Winery Wine Tasting Tour

    Let a local host-driver handle the road while you taste Driftwood wines

    From$185person

    What people are saying

    Review 1 of 5
    5/5

    Winding Road Hill Country Wine Tours was absolutely fabulous in all areas from booking to drop off! Richard reached out right after booking to provide confirmation, a layout of the tour and recommendations for our tour to ensure we would have the optimal experience. Then followed up a couple weeks before the tour verifying the schedule and inquiring of any changes. I chose to book with Winding Road Hill Country Wine Tours is because they offered a variety tour (one distillery, one winery, and a brewery) with the option for two persons, other tours required a minimum of four. Our host Eric was great, super friendly, checked us in at each location, gave us a time to met him for pickup so we could stay on schedule and get the most at each destination. It was a very enjoyable, relaxed tour exactly what we were hoping for. We were staying in Fredericksburg and toured Garrison Brothers Distillery (cocktails are fantastic and the burgers amazing), Becker Winery, Altstadt Brewery.

    Photo of Beth Crain

    Beth Crain

    October 19, 2026

    Review 1 of 1
    5/5

    Winding Road Hill Country Wine Tours was absolutely fabulous in all areas from booking to drop off! Richard reached out right after booking to provide confirmation, a layout of the tour and recommendations for our tour to ensure we would have the optimal experience. Then followed up a couple weeks before the tour verifying the schedule and inquiring of any changes. I chose to book with Winding Road Hill Country Wine Tours is because they offered a variety tour (one distillery, one winery, and a brewery) with the option for two persons, other tours required a minimum of four. Our host Eric was great, super friendly, checked us in at each location, gave us a time to met him for pickup so we could stay on schedule and get the most at each destination. It was a very enjoyable, relaxed tour exactly what we were hoping for. We were staying in Fredericksburg and toured Garrison Brothers Distillery (cocktails are fantastic and the burgers amazing), Becker Winery, Altstadt Brewery.

    Photo of Beth Crain

    Beth Crain

    October 19, 2026