Russian River Valley · Sonoma County
Visit Oak Tree Winery with a Private Chauffeur
A small family label pouring seven wines in a shared wine lounge in downtown Windsor, open into the evening late in the week, and a suggested six-hour day of tasting around it.
Book a Six-Hour Wine Tour
About the Winery
Oak Tree Winery is the family label of owners Michael and Abbie, who take pride in a hands-on approach to making wine from small, family-owned vineyards in the heart of Sonoma County.
The grapes come from the Alexander Valley and the Russian River Valley, and the lineup is seven wines: Cabernet Sauvignon, Merlot, a red blend, Pinot Noir, Sauvignon Blanc, Viognier and a Rosé of Pinot Noir.
Oak Tree pours at Tasting Notes Wine Lounge Collective on Windsor Road, in downtown Windsor, a shared tasting lounge that stays open into the evening Thursday to Sunday. That makes it a natural last stop of the day, and on Thursday and Friday afternoons happy hour brings $10 glasses, 15% off bottles and $5 off charcuterie.
Tasting Fees
Tasting fees to be verified upon reservation. Happy hour glasses are $10.
Tasting fees as of September 2026. Wineries set and collect their own fees, and they change from time to time.
At a Glance
Location
9086 Windsor Road, Windsor
AVA
Russian River Valley
Visiting
Open Thursday 2 to 6 p.m., Friday 1 to 8 p.m., Saturday noon to 8 p.m. and Sunday noon to 5 p.m.; closed Monday to Wednesday. Tastings can be booked through the winery's website.
Known For
Cabernet Sauvignon, Merlot, Pinot Noir, Viognier and a Rosé of Pinot Noir from Alexander Valley and Russian River Valley vineyards
Founded
Not published
Good to Know
Happy hour runs Thursday and Friday, 3 to 6 p.m., except during events: $10 glasses, 15% off bottles and $5 off charcuterie.
A Suggested Six-Hour Day
Pickup at 10:25 a.m. from a Healdsburg hotel such as Hotel Healdsburg or Harmon Guest House.
10:25 · Pickup at Hotel Healdsburg or Harmon Guest House
Hotel Healdsburg, on the town plaza, and Harmon Guest House, a boutique hotel just off the plaza, are each about 5 minutes from Smith Story at Bacchus Landing. Oak Tree opens in the afternoon, so it is the last stop of this day. The day below fits a six-hour tour, and extra time can be added by the hour.
10:30 · Smith Story Wine Cellars
About 5 minutes away. Ali and Eric Story's founder-led winery at Bacchus Landing on Westside Road, making small-lot Pinot Noir, Sauvignon Blanc and Cabernet Franc blends from cool-climate family vineyards; morning reservations bring private time with the Storys themselves, then a glass in the wine garden. The Fabulous Five flight is $25 and the Pinot Noir Chapters $50, each about an hour. Mornings by reservation from 10:30 a.m.; walk-ins from 1 p.m.
11:40 · Due Ruscelli Vineyards & Winery
About 10 minutes away. Michael and Melissa's family micro-winery on Limerick Lane, started in 2011 and named for the two seasonal creeks that frame its vineyard, making Italian varieties such as Primitivo, Sangiovese and Barbera; a family member hosts and shows how the whole process works. The Winemaking Tour and Private Tasting is $40, and a tasting with charcuterie $60. Walk-ins Friday to Sunday, 11 a.m. to 5 p.m.; other days by appointment, booked a day ahead.
1:00 · Lunch at Russian River Brewing
About 20 minutes away. The Windsor brewery and pub of Russian River Brewing, which first brewed Pliny the Elder in 1999, with a full pub menu and a self-guided brewery tour. Open daily from 11 a.m. Prefer a picnic? We can arrange a catered picnic at a winery that allows one; the cost is quoted when you book.
2:20 · Oak Tree Winery
A tasting of Oak Tree's seven wines at Tasting Notes Wine Lounge Collective in downtown Windsor, about an hour; the fee is confirmed when we book.
3:20 · Back to your hotel
Back in Healdsburg by 3:35 p.m., within six hours of pickup.
Three wineries is the right pace for a day of serious tasting. Oak Tree pours Thursday to Sunday from the afternoon, so it closes out this day, which works Thursday to Sunday.
About $65 to $90 per person in tasting fees for Smith Story and Due Ruscelli's winemaking tour, paid directly to each winery; Oak Tree's tasting fee is to be verified upon reservation.
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
When is Oak Tree Winery open?
Thursday 2 to 6 p.m., Friday 1 to 8 p.m., Saturday noon to 8 p.m. and Sunday noon to 5 p.m., at Tasting Notes Wine Lounge Collective in Windsor. When you book a tour with us, your chauffeur makes the reservation for you.
How much is a tasting at Oak Tree?
Oak Tree does not publish a tasting fee, so tasting fees are to be verified upon reservation. Happy hour glasses are $10 on Thursday and Friday, 3 to 6 p.m.
What wines does Oak Tree make?
Seven: Cabernet Sauvignon, Merlot, a red blend, Pinot Noir, Sauvignon Blanc, Viognier and a Rosé of Pinot Noir.
Who owns Oak Tree Winery?
Owners Michael and Abbie, a family operation working with small, family-owned vineyards.
Where does Oak Tree pour?
At Tasting Notes Wine Lounge Collective, 9086 Windsor Road in downtown Windsor.
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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