Dry Creek Valley · Sonoma County
Visit We Know Jack with a Private Chauffeur
Estate Zinfandel from a ridgetop Rockpile vineyard above Lake Sonoma, poured at a private tasting room above the barrels near Healdsburg, and a suggested six-hour day of tasting around it.
Book a Six-Hour Wine Tour
About the Winery
We Know Jack is the label of Lori Hunt and Mark Zuckerman, a former corporate flight attendant with a gift for wine and a Massachusetts pathologist with a love of vineyard science. After years of trips to wine country they bought the property of Jack Florence Sr., whom they found described as a legendary winegrower: he came to Dry Creek Valley in the mid-1970s and was a founding member of the Dry Creek growers' association, and his son, Jack Jr., planted ridgetop vineyards on Rockpile and helped establish the Rockpile appellation in 2002.
The Jack Florence Sr. Vineyard, planted between 1998 and 2002, is 9.5 acres of Zinfandel with some Syrah and Petite Sirah, at 1,250 feet on a ridge overlooking Lake Sonoma, in the zone where Rockpile and Dry Creek Valley overlap. The Zinfandel vines come from cuttings of 1880s vines at St. Peter's Church in Cloverdale, now called the Rockpile clone, and the fruit once went to Kent Rosenblum. The vineyard runs on solar power, is never tilled and is farmed and picked by hand. James MacPhail makes the wines, and the 2022 Rockpile Zinfandel won Best of Class and Double Gold at the 2026 Los Angeles Invitational Wine Competition.
Tastings are held at Grapewagon, the MacPhail family's small winery a few minutes from the Healdsburg roundabout, in a private, quiet room upstairs above the production floor. You taste about five wines available only here, all from the estate vineyard, over about 90 minutes.
Tasting Fees
The tasting of about five estate wines is currently complimentary, though the winery hopes you will buy a bottle. Tasting fees to be verified upon reservation.
Tasting fees as of September 2026. Wineries set and collect their own fees, and they change from time to time.
At a Glance
Location
851 Magnolia Drive, Healdsburg
AVA
Dry Creek Valley
Visiting
Private tastings by reservation and on request, Tuesday to Saturday at 11 a.m. and 2 p.m. Request through the winery's form, by email or by phone, with as much notice as possible.
Known For
Estate-grown Rockpile Zinfandel, including Rockpile Riff Raff
Founded
Estate vineyard planted 1998 to 2002
Good to Know
Up to 6 guests in the upstairs room, reached by 19 stairs; the winery will try to host guests who cannot manage stairs on the ground floor. No children or pets, as this is a working winery. Production is very small.
A Suggested Six-Hour Day
Pickup at 10:50 a.m. from a Healdsburg hotel such as h2hotel or Harmon Guest House.
10:50 · Pickup at h2hotel or Harmon Guest House
H2hotel, just off the Healdsburg plaza, and Harmon Guest House, a boutique hotel just off the plaza, are each about 10 minutes from Grapewagon, the winery where We Know Jack pours, so we pick you up in time for the 11 o'clock tasting. The day below fits a six-hour tour, and extra time can be added by the hour.
11:00 · We Know Jack
The private tasting of about five estate wines at Grapewagon, about 90 minutes (currently complimentary).
12:40 · Lunch at Bravas Bar de Tapas
About 10 minutes away. James Beard finalists Mark and Terri Stark's tapas bar on Center Street, steps from the Healdsburg plaza, with paella, Spanish wines and tables indoors or outside. Open daily from 11:30 a.m. Prefer a picnic? We can arrange a catered picnic at a winery that allows one; the cost is quoted when you book.
1:50 · Mill Creek Vineyards & Winery
About 5 minutes away. A hand-built tasting room and a turning waterwheel a mile from the Healdsburg plaza. The Signature Flight of five wines is $30 and the Reserve Flight $40, each seated outdoors by the waterwheel, for parties of 6 or fewer; allow 60 to 90 minutes. Seatings daily until 3:30 p.m.; reservations recommended.
3:30 · Amphora Winery
About 20 minutes away. A potter-winemaker's winery that ferments and ages wine in handmade terracotta amphorae from Italy, at historic Timber Crest Farms. A tasting is $25, seated outdoors under a shade structure or standing at the bar, for groups of up to 6. Tastings every half hour from 11 a.m., the last at 3:30 p.m.; walk-ins welcome, reservations appreciated.
4:45 · Back to your hotel
Back in Healdsburg by 4:45 p.m., within six hours of pickup.
Three wineries is the right pace for a day of serious tasting. We Know Jack pours Tuesday to Saturday, so this day works Tuesday to Saturday. Amphora's last tasting starts at 3:30, so we leave Mill Creek around 3:10.
About $55 to $65 per person for Mill Creek and Amphora, paid directly to each winery; the We Know Jack tasting is currently complimentary.
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 We Know Jack?
Yes. All tastings are by reservation and on request, Tuesday to Saturday at 11 a.m. and 2 p.m. When you book a tour with us, your chauffeur makes the reservation for you.
How much is a tasting at We Know Jack?
The tasting is currently complimentary; any future fee is to be verified upon reservation.
Where is the We Know Jack vineyard?
On a ridge at 1,250 feet overlooking Lake Sonoma in the Rockpile appellation, about 19 miles northwest of Healdsburg. Tastings are held at Grapewagon, a winery a few minutes from Healdsburg.
Who makes We Know Jack wine?
James MacPhail, at his family's Grapewagon winery, from the estate Jack Florence Sr. Vineyard.
What is Rockpile Riff Raff?
We Know Jack's estate, single-block Zinfandel with a little of its own Petite Sirah, from the Jack Florence Sr. Vineyard.
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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