Austin · San Antonio
The Hill Country,
Poured Just for You
Effortless, all-inclusive wine tours through the Texas Hill Country. We handle the driving, the reservations, and every tasting fee — you just sit back, sip, and enjoy the view.
Celebrations,
Done Right
Bachelorette weekends, milestone birthdays, anniversaries — the days worth remembering deserve more than a rideshare and a rushed reservation. We make the whole thing effortless.
- Door-to-door pickup available from your hotel, Airbnb, or home
- Reserved stops chosen for you — hand-selected 3 wineries, or choose to mix in a brewery, distillery, or village lunch
- Chilled cooler on board for the bottles you fall for
- Your host handles the driving, the pouring, and the group photos
- Charcuterie boards & breakfast taco add-ons available
- Add an optional décor package — sashes, banners & balloons
How the Day Works
All you bring is good company. We take care of the rest.
Book Your Day
Pick a date and tell us the occasion. We'll shape the tour around your group.
We Come to You
Door-to-door pickup in the shuttle — from your hotel, Airbnb or home in New Braunfels, Gruene, Wimberley and across the Hill Country. No driving, no directions, no designated driver.
Taste the Best
Reserved tastings at three standout Hill Country wineries, with a host who knows them.
Home Safe
New favorites chilling in the cooler, and a ride home right to your door.
Hungry? Water, non-alcoholic drinks, and light snacks are always on board, included. Add breakfast tacos at pickup or personal charcuterie boards, pre-ordered 48 hours ahead. Lunch isn't included — but you'll have time to grab a bite at the stops, and our Wine + Village tours build in a village lunch stop.
Find Your Tour
All-inclusive wine tour packages from $145 per person, tastings included. Choose a region, then pick your flavor. Most days the shuttle is yours alone — occasionally we'll pair two parties booked on the same date and route, and we'll always let you know first.
Wimberley & Driftwood Wine Tour
Standout Driftwood wineries paired with the charm of Wimberley village — the Hill Country classic that started it all.
Johnson City Wine Tour
Rolling vineyards and small-town Texas charm, a little off the beaten path and all the better for it.
Fredericksburg Wine Tour
The marquee Hill Country wine town — a full, unhurried day among its most-loved estates. A longer drive, worth every mile.
- Classic — three hand-picked wineries, our signature day out
- Wine + Village — two wineries plus a village stop for lunch and a wander
- Mix Your Own — build your own trio, or swap in a brewery or distillery
Fully Custom & Group Days
Design your own day — pick your stops, mix wineries, breweries and distilleries, or build something bigger for a group. Driver and 13-seat shuttle, BYOB.
What Groups Are Saying
Rated 5.0 · 31 five-star reviews on Google
“It was like going on a tour with one of your friends. The wineries were fantastic, and they gave us great recommendations for places to eat since we're new to the area. Highly recommend.”
“Booked this tour for my 30th birthday, and it was an absolute blast! Richard and Meghan did an amazing job showing us the best wineries in the Texas Hill Country — everything was seamless, and they went above and beyond to make my birthday feel special.”
“We absolutely LOVED our wine tour with Winding Road on our ‘mini-moon’ in Gruene — easily our favorite part of the trip! The bus was comfortable and spotless, they tailored the day to us, and it was a fun, relaxing way to explore the Texas Hill Country.”
A Texan, an Irishwoman, & one very lucky road
Hi, we're Richard & Meghan.
Richard was born and raised right here in Texas. Meghan made the leap a little further — trading the green hills of Ireland for the vineyards of the Hill Country. Between the two of us, we've tasted our way across both sides of the Atlantic, and there's nothing we love more than sharing a great glass with good company.
We've been blessed to travel the globe together, experiencing some of the best wines in the world, but would easily put them up against Texas's best vintages — after all, things are always bigger and better in Texas! We can't wait to welcome you to the Winding Road!
Your Hill Country Day Awaits
Check live availability and book in a few clicks — or call us and we'll build the perfect day with you.
Check Availability & Book