Diamond Mountain District · Napa Valley
Visit Checkerboard with a Private Chauffeur
A private Diamond Mountain estate with a winery, a cave and four vineyards, visited by private request, and a suggested six-hour day of tasting around it.
Book a Six-Hour Wine Tour
About the Winery
Checkerboard Vineyards sits on the southeast-facing slope of Diamond Mountain in the Diamond Mountain District. Vintners Dennis O'Neil and Steph Martin built a 300-acre estate with a winery, a cave and four vineyard sites, joined by a drive of two and a half miles that climbs from the valley floor to the top of the ridge.
The wines are small lots led by Cabernet Sauvignon. Aurora Vineyard sits on a knoll about 1,200 feet up the mountain, with volcanic soils of basalt cobble and red clay on one side and white volcanic ash on the other; it also supplies the Kings Row bottling. The estate is farmed under the Fish Friendly Farming program, with permanent cover crops and care for Nash Creek.
Checkerboard does not run a public tasting room or publish tastings. Visits are by private request; we contact the estate on your behalf and confirm what it can offer. The owners also keep rescued animals on the property, including an Angus cow named Angie and a sheep called Lamb Chop.
Tasting Fees
Checkerboard does not publish a tasting fee. Any private visit and its cost are confirmed by the estate when the request is accepted.
Tasting fees as of September 2026. Wineries set and collect their own fees, and they change from time to time.
At a Glance
Location
4331 Azalea Springs Way, Calistoga
AVA
Diamond Mountain District
Visiting
No public tastings are published. Visits are by private request to the estate, which we make on your behalf.
Known For
Small-lot Diamond Mountain Cabernet Sauvignon from four estate vineyards, including Aurora Vineyard
Founded
Good to Know
Private requests depend on the estate's schedule, so ask well ahead. The estate drive climbs about two and a half miles up the mountain.
A Suggested Six-Hour Day
Pickup at 10:00 a.m. from a nearby hotel such as Four Seasons Napa Valley or Calistoga Motor Lodge.
10:00 · Pickup at Four Seasons Napa Valley or Calistoga Motor Lodge
Four Seasons Napa Valley, on the Silverado Trail, is about 12 minutes from the estate, and Calistoga Motor Lodge, a restored mid-century lodge in town, is about 10 minutes away. The day below fits a six-hour tour, and extra time can be added by the hour.
10:15 · Checkerboard Vineyards
A private visit by request. We plan about an hour; the format and any fee are confirmed by the estate.
11:30 · Jericho Canyon Vineyard
About 15 minutes away. A hillside estate in the eastern hills above Calistoga. The Private Estate Tasting starts with an ATV tour of the vineyard and winery, then a seated tasting, $100 and about 75 minutes (waived with a three-bottle red wine purchase per person). By appointment only.
1:00 · Lunch at Brasswood Bar + Kitchen
About 15 minutes away. Lunch at Brasswood Bar + Kitchen on Highway 29 between St. Helena and Calistoga, a sit-down restaurant 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.
2:25 · Sherwin Family Vineyards
About 18 minutes away. A family winery high on Spring Mountain, with tastings in the tasting room or on the patio. The Winery Tasting is $95 (plus booking fees), by appointment, waived with a minimum wine purchase.
3:25 · Back to your hotel
About 25 minutes back to Calistoga, so back by about 3:50 p.m., within six hours of pickup.
About $195 per person in tasting fees for Jericho Canyon and Sherwin, paid directly to each winery, plus any fee Checkerboard sets for a private visit.
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 Checkerboard?
Yes. Checkerboard has no public tasting room, and visits are by private request only. We send the request and confirm what the estate can offer. When you book a tour with us, your chauffeur makes the reservation for you.
How much is a tasting at Checkerboard?
Checkerboard does not publish a tasting fee; any fee for a private visit is set by the estate when it accepts the request, as of September 2026.
Who owns Checkerboard Vineyards?
Vintners Dennis O'Neil and Steph Martin.
What is Checkerboard known for?
Small-lot Cabernet Sauvignon from four estate vineyards on Diamond Mountain, including Aurora Vineyard, about 1,200 feet up on a volcanic knoll.
Is Checkerboard on Diamond Mountain?
Yes. The estate runs from the valley floor up the southeast-facing slope of Diamond Mountain, with a winery, a cave and four vineyard sites.
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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