Off the Beaten Path · From New Braunfels, San Antonio & Austin
The Johnson City
Wine Tour
The quieter side of Texas wine country — rolling vineyards and small-town charm at the eastern gateway of the 290 Wine Road, paired with a stop in downtown Johnson City. It's an easygoing day out (about 5.5 hours), and our Gruene-based team handles the driving, the reservations, and every tasting fee — you just sip and enjoy the Hill Country. From $145 per person.
Johnson City — off the beaten path
Johnson City sits at the eastern gateway of the 290 Wine Road — the same celebrated wine country as Fredericksburg, just quieter and more relaxed. Rolling vineyards, family-run estates, and tasting rooms with room to breathe, without the crowds. It's a shorter drive than Fredericksburg too, so it makes an easygoing day: reserved tastings at a handful of favorites, at an unhurried pace, with all the driving handled for you.
Downtown Johnson City — where the day slows down
The little town itself is worth the stop — a historic courthouse square, local kitchens, and an easy small-town pace. On our Wine + Village flavor, we trade the third tasting for a lunch stop in downtown Johnson City, so you can stretch your legs and eat well before the ride home.
The Wineries We Build Your Day Around
A Classic day is three standout tasting rooms, chosen with you and reserved for your group. Because we pick up anywhere from Austin to San Antonio, we route the day to break up the drive — so your exact lineup flexes with where you start. Here are some of our favorites. Prefer beer or spirits? Swap a stop on the Mix Your Own flavor below.
Lewis Wines
Among the Hill Country's most respected labels — a 100-acre estate just west of Johnson City.
Ron Yates
An acclaimed winemaker's striking new estate room on 290 in Hye, with vineyard views and a wood-fired kitchen.
Sandy Road Vineyards
A small family-run estate pouring award-winning 100% Texas wine, with tastings in the treehouse.
A few of our favorites — we'll build your three around your pickup and your group, and add more over time.
Building a Mix Your Own day? Johnson City has more than wine.
Brewery
- Pecan Street BrewingHandcrafted beer and a scratch kitchen in a dog-friendly downtown biergarten (open daily except Wed)
Distillery
- Andalusia Whiskey Co.Texas single-malt & bourbon flights, walk-in friendly, just south in Blanco (open Mon–Sat)
Stops are subject to availability and may change; we'll confirm your final line-up on your itinerary. Winding Road is an independent tour operator and is not affiliated with, sponsored by, or endorsed by the wineries, breweries, or distilleries named here.
Choose Your Flavor
Prices per person, tastings included, tip excluded.
Classic
Three reserved Johnson City wineries in a relaxed ~5.5-hour day. Our signature outing, and the easiest way to see the quiet end of the 290 Wine Road.
Wine + Village
Two Johnson City wineries plus a lunch stop in the little downtown — a historic courthouse square, local kitchens, and time to stretch your legs on your own.
Mix Your Own
Three stops, your call — mix wineries with a brewery (Pecan Street) or a distillery (Andalusia) in and around Johnson City. Beer, spirits, or one of each, chosen at checkout.
Prefer to design the whole day yourself? Our Fully Custom option is a driver + 13-seat shuttle by the hour (BYOB), from $100/hour with a 4-hour minimum.
How the Day Works
We Pick You Up
Door-to-door in the 13-seat shuttle — no driving, no directions, no designated driver. Your exact pickup time varies by location; we confirm it on your itinerary.
First Pours
Reserved tastings begin at Johnson City's rolling-vineyard estates, with a host who knows them.
Taste & (Optionally) Lunch
Keep tasting on Classic, or on Wine + Village trade a stop for a lunch break in downtown Johnson City.
Home Safe
New favorites chilling in the cooler, and a ride back to your door.
Water, soft drinks, and light snacks are included on board. Add breakfast tacos or a charcuterie board, pre-ordered 48 hours ahead. Lunch isn't included — you'll have time to grab a bite at the wineries, and Wine + Village builds in a lunch stop in downtown Johnson City.
Pickup & Zones
Door-to-door pickup from your home, hotel, or Airbnb — including across Austin and San Antonio. Pickup is charged per booking, not per person.
Doorstep pickups shift your start and return times by the drive to and from your address. Your confirmed itinerary always shows exact times.
Add-Ons
Optional extras to round out the day. Food add-ons are pre-ordered 48 hours ahead so we get quantities right.
Charcuterie Board
Per person. A personal board to graze on during a wine tasting.
Breakfast Tacos
Per person, two each at pickup. Veggie option available.
Décor Package
Sashes, banners & balloons for a bachelorette, birthday, or other celebration.
Extend the Day
Per hour ($100–125). Add time for another stop or a longer lunch.
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.”
Explore Other Regions
Johnson City is our off-the-beaten-path day out — but the Hill Country is big. Pick the region that fits your group; every tour includes the same door-to-door pickup and tastings.
Wimberley & Driftwood
The easiest wine country to reach from Austin — celebrated Driftwood wineries plus the charm of Wimberley village. From $145/person.
See the Driftwood tourFredericksburg
The celebrated estates of the 290 Wine Road paired with Fredericksburg's historic German Main Street — a fuller day out. From $160/person.
See the Fredericksburg tourCustom & Groups
Build the whole day yourself, or plan a bigger celebration — driver and 13-seat shuttle by the hour.
See all tour optionsQuick Questions
Which wineries will we visit?
A Classic day visits three standout tasting rooms, chosen with you and reserved for your group. Since we pick up anywhere from Austin to San Antonio, we route the day to break up the drive — so your lineup flexes with where you start. A few of our favorites include Lewis Wines, Ron Yates, and Sandy Road Vineyards, with more added over time. We confirm the final line-up on your itinerary.
Are tasting fees really included?
Yes. Your per-person price covers transportation and every tasting fee at your reserved stops — nothing extra to pay at the winery. Lunch and any bottles you take home are the only things you'll spend on.
Can we do beer or spirits instead of all wine?
Absolutely — that's the Mix Your Own flavor. Swap a winery for a brewery — Pecan Street Brewing in downtown Johnson City — or a distillery — Andalusia Whiskey Co., with Texas whiskey flights just south in Blanco. Beer, spirits, or one of each; you choose your three stops at checkout.
How long is the Johnson City day?
About 5.5 hours, roughly 10:30 AM to 4:00 PM — an easygoing day, a little shorter than our Fredericksburg tour. Doorstep pickup times shift with your address; your confirmed itinerary shows exact times.
Where do you pick us up?
Door-to-door, free across our home zone — Gruene, New Braunfels, Wimberley, Canyon Lake, and San Marcos. Pickup into the Austin–San Antonio corridor is free for private groups of 6+, or a $50 intro rate for smaller groups.
Is the tour private?
Almost always, yes — the shuttle is usually yours alone. On the rare occasion two parties have booked the same date and the same itinerary, we may combine them, and we'll tell you before your tour. If you'd rather not share, just say so and we'll work it out.
What if our date isn't available?
Ask anyway. An unavailable date usually means another group already has the shuttle that day — but there's often room to join them. Call or text 830-355-VINO (8466) and we'll tell you where we're headed, so you can decide whether it suits your group.
Your Johnson City Day Awaits
Check live availability and book in a few clicks — or call us and we'll build the perfect day with you.
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