Chalk Hill · Sonoma County
Visit Two Shepherds with a Private Chauffeur
A natural wine producer pouring small lots of uncommon varieties inside its Windsor winery on Fridays and Saturdays, and a suggested six-hour day of tasting around it.
Book a Six-Hour Wine Tour
About the Winery
Two Shepherds is a small natural wine producer in Windsor, founded by former wine writer William Allen. The first harvest was in 2010, the first release in 2011 was 175 cases of five wines, and the winery moved into its own facility in 2015, the year Karen officially joined. Production has grown to about 5,000 cases, still made in lots of 25 to 400 cases, which is why the winery calls William the insane master of small lots.
The wines started with Rhône varieties and now range widely: Trousseau Gris, Pinot Meunier, Cinsault from the Bechtoldt vineyard, Carignan, Vermentino, Picpoul, skin-fermented orange wines and sparkling wine in cans. The approach has not changed since day one: organic or old-vine fruit from small family vineyards, native yeast, neutral barrels, whole clusters, minimal sulfur, and no fining or filtering.
The tasting room is inside the winery, so you see exactly how the wines are made. It sits in the Windsor beverage district among a cidery, a distillery and other small wineries, with Russian River Brewing among the neighbors. We confirm current details when we book.
Tasting Fees
The winery does not publish a fee for tastings in the Windsor tasting room; we confirm it when we book. $50 per person for the private Vineyard Tasting with the winemaker at the farm, including a farm and animal tour, waived with a purchase of three bottles per person.
Tasting fees as of October 2026. Wineries set and collect their own fees, and they change from time to time.
At a Glance
Location
7763 Bell Road, Windsor
AVA
Chalk Hill
Visiting
The tasting room in the winery is open Friday and Saturday, noon to 5 p.m.; no reservation is required. Private vineyard tastings at the family farm are by reservation, Monday to Saturday, by email.
Known For
Natural wines from uncommon varieties, such as Grenache Blanc, Trousseau Gris, Carignan and Cinsault, plus orange wines and sparkling wine in cans
Founded
2010 (first harvest)
Good to Know
The tasting room is open only on Fridays and Saturdays, and the team takes Sunday off. The farm address for vineyard tastings is not public and comes with the confirmation. The vineyard tasting includes a farm and animal tour.
A Suggested Six-Hour Day
Pickup at 11 a.m. from a Windsor hotel such as Hampton Inn & Suites Windsor or Holiday Inn Windsor. Two Shepherds is about 10 to 15 minutes away.
11:00 · Pickup at Hampton Inn & Suites Windsor or Holiday Inn Windsor
Both hotels are in Windsor, about 10 to 15 minutes from every stop today. The day is set for a Friday or Saturday, when the Two Shepherds tasting room is open. Extra time can be added by the hour.
11:15 · La Crema Estate at Saralee's Vineyard
About 15 minutes away. Seated tastings of cool-climate Chardonnay and Pinot Noir in a 1900 hop barn. The seated Estate Tasting of six wines is $35; plan on about 75 minutes.
12:45 · Two Shepherds
About 15 minutes away. A tasting of natural wines inside the winery, about an hour. No reservation is needed on Fridays and Saturdays; we confirm the fee when we book.
1:50 · Lunch at Russian River Brewing Company
A few minutes away. Lunch at the brewery's Windsor pub, a neighbor of Two Shepherds, with a full kitchen, open daily from 11 a.m. We confirm hours when we book. Prefer a picnic? We can arrange a catered picnic at a winery that allows one; the cost is quoted when you book.
3:05 · J Vineyards & Winery
About 15 minutes away. Traditional-method sparkling wine and Pinot Noir. The standing Signature Tasting of five wines is $35, about an hour; walk-ins are welcome for it.
4:20 · Back to your hotel
Back by 5:00 p.m., six hours after pickup.
The Two Shepherds tasting room is open only Friday and Saturday, noon to 5 p.m., so this day suits a Friday or Saturday. La Crema is open daily, 10 a.m. to 5 p.m., and J Vineyards Thursday to Monday, 11 a.m. to 5 p.m. On other days we can request a private vineyard tasting with the winemaker instead.
About $70 per person at La Crema and J Vineyards, plus the Two Shepherds tasting fee, which we confirm when we book. Fees are paid directly to each winery.
Every tour is custom. This day is a starting point: your chauffeur will shape it around what matters to you, and we plan multi-day tours for guests who want to see more of wine country.
Your Vehicle & Six-Hour Tour Rates
Up to 6 guests
Elite Luxury SUV
Lincoln Navigator or Cadillac Escalade
From $750
Six-hour wine tour, plus 20% gratuity. Additional hours $125 each.
Up to 9 guests
Jet Sprinter or Executive Luxury Van
Captain's chairs and room to spread out
From $1,350
Six-hour wine tour, plus 20% gratuity. Additional hours $225 each.
Larger groups travel in more than one vehicle, and we plan the winery appointments around your group, since many wineries limit groups to 6 to 8 guests. Tasting fees are separate and paid directly to each winery. Every tour starts with six hours; add time by the hour when you book.
Questions
Do I need a reservation at Two Shepherds?
Not for the Windsor tasting room, which is open Friday and Saturday, noon to 5 p.m., with no reservation required. The private vineyard tasting at the farm is by reservation. When you book a tour with us, your chauffeur arranges the visit for you.
How much is a tasting at Two Shepherds?
The winery does not publish a fee for the tasting room. The private Vineyard Tasting is $50 per person, waived with a purchase of three bottles per person. We confirm current prices when we reserve, as of October 2026.
Where do guests taste at Two Shepherds?
In the winery itself, at 7763 Bell Road in Windsor. Vineyard tastings are at the family farm, whose address comes with the confirmation.
Who runs Two Shepherds?
Founder and winemaker William Allen, a former wine writer, who made the first harvest in 2010. Karen officially joined Two Shepherds in 2015.
What is Two Shepherds known for?
Natural wines in small lots from uncommon varieties, made with native yeast in neutral barrels and bottled unfined and unfiltered, including orange wines and sparkling wine in cans.
How does booking a tour with Bien Chauffeured work?
Reserve a six-hour tour online, even if your plans are still taking shape. Your chauffeur will email you first to learn what matters to you, then build your itinerary and make the winery appointments. Extra hours can be added.
Reserve Your Tour Now, Plan the Details Later
Your plans don't need to be final to book. Reserve your six-hour tour online, and your chauffeur will email you first to learn what matters to you, then build your itinerary and make the winery appointments. Prefer to talk? Call our concierge at 833-915-2436.
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