St. Helena · Napa Valley
Visit Dakota Shy with a Private Chauffeur
A small Cabernet Sauvignon house on a historic estate at the base of Pritchard Hill, and a suggested six-hour day of tasting around it.
Book a Six-Hour Wine Tour
About the Winery
Dakota Shy began in 2012, when two friends and business partners who had worked under other Napa winemakers set out to make their own Cabernet Sauvignon. In 2014 they bought a historic estate on Sage Canyon Road from the de Limur family and built a new winery there. Winemaker and owner Tom Garrett leads the winery today with partner and general manager Ryan Clark.
The estate sits at the base of Pritchard Hill, on land that was part of George Yount's Rancho Caymus grant of 1836. In the 1850s it was a stop on the wagon road toward Calistoga and Sage Canyon. Charles de Limur planted its redwoods, magnolias and 1.2 acres of Italian and Spanish olives, which the winery still presses for its own oil.
The wines are Cabernet-based and made in small lots from partner vineyards across Napa Valley, including Atlas Peak, Howell Mountain, Oakville and Rutherford. Visits are by appointment only, and each one is a private tasting: a guided walk around the grounds and the winery, then a seated tasting. Plan on about 75 minutes.
Tasting Fees
$125 for the Estate Tasting, a showcase of the core wines, and $175 for the Single Vineyard Tasting of the most limited Cabernets, each about 75 minutes with a tour of the estate.
Tasting fees as of September 2026. Wineries set and collect their own fees, and they change from time to time.
At a Glance
Location
771 Sage Canyon Road, St. Helena
AVA
Napa Valley
Visiting
By appointment only. Book online through Tock, or by phone or text at 707-244-1184.
Known For
Small-lot, Cabernet Sauvignon-based wines from single vineyards across Napa Valley
Founded
2012 (estate acquired in 2014)
Good to Know
Online reservations are for parties of 1 to 6. Every visit is a private, seated tasting that starts with a tour of the grounds and winery. Tock shows only some of the available times, so call or text the winery for more options.
A Suggested Six-Hour Day
Pickup at 10:00 a.m. from a nearby hotel such as Auberge du Soleil or Harvest Inn.
10:00 · Pickup at Auberge du Soleil or Harvest Inn
Stay close and the tasting starts right away. Auberge du Soleil, a hillside resort above Rutherford, is about 6 minutes from Dakota Shy, and Harvest Inn, a vineyard-side resort on the south edge of St. Helena, is about 12 minutes away. The day below fits a six-hour tour, and extra time can be added by the hour.
10:15 · Dakota Shy
The Estate Tasting ($125), with a tour of the grounds and winery and a seated tasting, about 75 minutes. The Single Vineyard Tasting ($175) runs about the same length.
11:40 · Beaulieu Vineyard
About 8 minutes away. Beaulieu has restored its original 1885 winery as its hospitality center. The 1885 Tasting there is $50 for 60 minutes and ends with the Georges de Latour Private Reserve Cabernet Sauvignon. Open daily 10 a.m. to 5 p.m., by reservation.
12:55 · Lunch at Farmstead at Long Meadow Ranch
About 10 minutes away. Lunch at Farmstead on Main Street in St. Helena, open daily for lunch from 11:30 a.m. (11 a.m. on weekends). Prefer a picnic? We can arrange a catered picnic at a winery that allows one; the cost is quoted when you book.
2:15 · Caymus Vineyards
About 10 minutes away. Chuck Wagner and his parents opened Caymus in 1972 with 240 cases of Cabernet Sauvignon, and the family still owns and runs it. The seated tasting is $50 and takes 1.5 hours. By appointment; seated tastings run 9:30 a.m. to 3:30 p.m.
3:45 · Back to your hotel
Back by 4:00 p.m., six hours after pickup.
Optional: Mumm Napa
Adds about an hour. A sparkling wine house on the Silverado Trail with a patio facing the vineyards and mountains. Reservations are recommended, and walk-ins are taken when tables are free. Sip & Sparkle is from $48, 60 minutes. All guests must be 21 or over; last seating at 5 p.m.
About $225 to $275 per person in tasting fees for the three wineries, paid directly to each winery.
Three wineries is the right pace for a day of serious tasting. The fourth stop is there if the day allows.
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 Dakota Shy?
Yes. Dakota Shy welcomes visitors by appointment only, booked through Tock or by calling or texting the winery. When you book a tour with us, your chauffeur makes the reservation for you.
How much is a tasting at Dakota Shy?
$125 per person for the Estate Tasting and $175 for the Single Vineyard Tasting, each about 75 minutes, as of September 2026.
What is Dakota Shy known for?
Cabernet Sauvignon-based wines made in small quantities, including single-vineyard Cabernets from sites such as Atlas Peak, Howell Mountain, Oakville and Rutherford.
Who owns Dakota Shy?
Winemaker and owner Tom Garrett runs Dakota Shy with partner and general manager Ryan Clark.
What is the history of the Dakota Shy estate?
The land was part of the Rancho Caymus grant of 1836 and was a wagon-route stop in the 1850s. The de Limur family owned it for decades and planted its redwoods, magnolias and olives before Dakota Shy bought it in 2014 and built its winery.
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 888-291-2328.
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