Gruene · New Braunfels · Wimberley · Texas Hill Country
Austin · San AntonioNew Braunfels · Austin · San Antonio
Fredericksburg · Driftwood · Wimberley
Austin · San AntonioNew Braunfels · Austin · San Antonio
Fredericksburg · Driftwood · Wimberley
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.All-inclusive Hill Country wine tours. We handle the driving, the reservations and every tasting fee.
Free door-to-door pickup — Austin, San Antonio, Fredericksburg & everywhere between
Gruene-BasedHill Country Roots
Door-to-DoorWe Pick You Up
All-InclusiveTasting Fees Included
13-SeatComfortable Shuttle
Tours Your WayClassic to Fully Custom
Our Signature Experience
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
- Your host handles the driving, the pouring, and the group photos
- Breakfast taco add-ons available at pickup
- Add an optional décor package — sashes, banners & balloons
Simple per-person pricing — the whole shuttle is yours, no group package fee.
Plan Your Day
Simple From Start to Sip
How the Day Works
All you bring is good company. We take care of the rest.
1
Book Your Day
Pick a date and tell us the occasion. We'll shape the tour around your group.
2
We Come to You
Door-to-door pickup in the shuttle, free — from your hotel, Airbnb or home in Austin, San Antonio, Fredericksburg, Johnson City and everywhere between.
3
Taste the Best
Reserved tastings at three standout Hill Country wineries, with a host who knows them.
4
Home Safe
New favorites chilling in the cooler, and a ride home right to your door.
Food & Drink
Hungry? Water, non-alcoholic drinks, and light snacks are always on board, included. Add breakfast tacos at pickup, 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.
Vines, Patios and Tasting Rooms
Where the Day Is Spent
A few of the stops we build days around — shaded patios, cool tasting rooms, and the odd long view. Your exact lineup flexes with where you start.
Three Regions · Four Packages
Find Your Tour
All-inclusive wine tour packages from $145 per person, tastings included. Choose a region, then pick your flavor. Every tour is private — the shuttle is yours alone, and we’ll only ever pair you with another group if you’ve told us that’s fine.
Wimberley & Driftwood Wine Tour
Closest to Austin & New Braunfels
Standout Driftwood wineries paired with the charm of Wimberley village — the Hill Country classic that started it all.
From $145 / personTastings included
Johnson City Wine Tour
Central Hill Country · routed to your pickup
Rolling vineyards and small-town Texas charm, a little off the beaten path and all the better for it.
From $145 / personTastings included
Fredericksburg Wine Tour
Our furthest day — worth the drive
The marquee Hill Country wine town — a full, unhurried day among its most-loved estates. A longer drive, worth every mile.
From $160 / personTastings included
Flavors
Every region, three ways to shape the day.
- 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. The hourly rate covers the driver and 13-seat shuttle only — you arrange and pay for tastings and food, and you’re welcome to bring your own drinks along.
From $100 / hour · 4-hour minimum
We Come to You
Where We Pick You Up
Door-to-door from your home, hotel, or Airbnb, in one of our shuttles and it's free — up to 13 passengers per shuttle. One pickup address per booking, no guest minimum.
AustinSan AntonioNew BraunfelsGruene
San MarcosWimberleyCanyon LakeDripping Springs
Johnson CityFredericksburgBoerneKyle
BudaBulverdeSchertz
Somewhere else? Just ask and we'll quote it. Doorstep pickups shift your start and return times by the drive to and from your address — your confirmed itinerary always shows exact times.
Loved by Our Guests
What Groups Are Saying
★★★★★
Rated 5.0 · 41 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.”
— Terry J.D.
★★★★★
“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.”
— Adrian C.
★★★★★
“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.”
— Claire M.
Our Story
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!
— Richard & Meghan
Let's Plan It
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 & BookPlanning something bigger, or have a question first? Send us a note and we’ll come back to you.