Texas's Marquee Wine Town · From San Antonio & AustinTexas's Marquee Wine Town
The Fredericksburg
Wine Tour
The heart of Texas wine country — the celebrated estates of the 290 Wine Road paired with Fredericksburg's historic German Main Street. A fuller day out, about 7 hours, with the driving, the reservations and every tasting fee handled for you. Three all-inclusive packages to choose from, and we pick up across San Antonio and Austin.
Fredericksburg — where Texas wine grew up
The 290 Wine Road is the most celebrated stretch of Texas wine country — dozens of estates strung along the highway east of town, home to many of the state's most-awarded labels. It's a longer haul than Driftwood, so we make it a fuller day: reserved tastings at the marquee names, at an unhurried pace, with all the driving handled for you.
Main Street Fredericksburg — where the day slows down
In town sits one of the prettiest main streets in Texas — a historic German settlement of biergartens, bakeries, and shops. On our Wine + Village flavor, we trade the third tasting for a Main Street lunch stop — schnitzel at Der Lindenbaum or a biergarten table at The Auslander — so you can stretch your legs and eat well.
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.
A few of our favorites — we'll build your three around your pickup and your group, and add more over time.
- Narrow Path WinerySmall-batch and family-run — an estate room near Stonewall plus a Main Street room
- Texas Wine CollectiveLively, group-friendly estate pouring wine and cider from several Texas labels
- Michael Ros Winery100% Texas fruit in a two-story room built into the hillside like an Italian piazza
- Signor VineyardsGardens and a 200-acre estate on the Pedernales, plus a room downtown in town
- Becker VineyardsAn iconic name in Texas wine, among the lavender fields in Stonewall
- Ab Astris WineryTwelve family-farmed acres between Stonewall and Hye — Tannat and Montepulciano under the oaks
- Sister Creek VineyardsOld-World reds in a restored 1885 cotton gin in Sisterdale, up from San Antonio
- RhinoryA tasting on a 55-acre ranch alongside Blake, a southern white rhino — experience proceeds fund conservation
Building a Mix Your Own day? Fredericksburg has more than wine.
Brewery
- Altstadt BreweryBavarian beer brewed to the 1516 German purity law — four ingredients, poured in a 120-acre biergarten on 290
Distillery
- 1693 DistilleryAward-winning whiskey and Elevación agave spirit — flights by the fire pit under light-strung oaks
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
Three all-inclusive Fredericksburg wine tour packages — a favorite for bachelorette weekends and milestone birthdays. Prices per person, tastings included, tip excluded.
Classic
Three reserved Fredericksburg wineries in a relaxed ~7-hour day. Our signature outing, and the fullest way to see the 290 Wine Road.
Wine + Village
Two 290 Wine Road wineries plus a lunch stop on historic Main Street Fredericksburg — schnitzel, a biergarten, and time to browse the shops on your own.
Mix Your Own
Three stops, your call — mix wineries with a brewery (Altstadt) or a distillery (1693) in and around Fredericksburg. 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 the 290 Wine Road's standout estates, with a host who knows them.
Taste & (Optionally) Lunch
Keep tasting on Classic, or on Wine + Village trade a stop for lunch on historic Main Street Fredericksburg.
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, 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 on Main Street Fredericksburg.
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.
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.
Add-Ons
Optional extras to round out the day. Food add-ons are pre-ordered 48 hours ahead so we get quantities right.
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 · 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.”
“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
Fredericksburg is our marquee 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 tourJohnson City
Rolling vineyards and small-town Texas charm, a little quieter and all the better for it. From $145/person.
See the Johnson City 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 Narrow Path, Texas Wine Collective, Michael Ros, Signor Vineyards, Becker Vineyards, Ab Astris, Sister Creek Vineyards, and Rhinory, 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 — Altstadt Brewery — or a distillery — 1693 Distillery, with whiskey and tequila flights just outside town. Beer, spirits, or one of each; you choose your three stops at checkout.
How long is the Fredericksburg day?
About 7 hours, roughly 10:00 AM to 5:00 PM — a little longer than our Driftwood day, since Fredericksburg is a longer drive and worth the fuller outing. Doorstep pickup times shift with your address; your confirmed itinerary shows exact times.
Where do you pick us up?
Door-to-door from your home, hotel, or Airbnb, and it's free — Austin, San Antonio and everywhere between, whatever the size of your group. That covers Gruene, New Braunfels, San Marcos, Wimberley, Canyon Lake, Dripping Springs, Johnson City, Fredericksburg, Boerne, Kyle, Buda, Bulverde and Schertz as well as the two cities. Free covers one pickup address per booking; if you need a second stop, just ask. Farther afield, we'll quote it.
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 Fredericksburg 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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