Healdsburg · Sonoma County
Private chauffeur service from Santa Rosa Airport, SFO or Oakland to Calderwood Inn in Healdsburg, and a six-hour wine tour that starts at the inn.
Book Your Ride or Wine Tour
Calderwood Inn is a Queen Anne Victorian built in 1902 for fruit grower John Miller, and it is listed as the John Miller House on the California and Sonoma County landmarks registry. Luther Burbank helped design the original landscape. It has been a bed and breakfast since the early 1980s, is now owned by the Wilson family, and has 10 rooms.
A gourmet breakfast is served in the dining room, with welcome wine on arrival and perks at Wilson Artisan Wineries. The gardens include an organic garden, and spa services are offered. One dog under 50 pounds is allowed in select rooms for $50.
It is also an easy place to start a wine tour. Rockpile Vineyards, Hirsch Vineyards and Stonestreet Estate Vineyards are all within about 10 minutes. We are based in Calistoga, in neighboring Napa Valley.
Sonoma County Airport (STS): about 11 miles, 20 minutes. The closest airport to Calderwood Inn, and the easiest arrival: a small airport in Santa Rosa with no Bay Area traffic on the drive. Direct flights come in from Los Angeles, San Diego, Seattle, Portland, Phoenix, Denver, Dallas and more.
Oakland (OAK): about 83 miles, 1 hour 45 minutes. Often a quieter airport than SFO.
San Francisco International (SFO): about 83 miles, 1 hour 50 minutes, and longer at busy times. The most flights, with a drive across the Bay Area.
Sacramento (SMF): about 114 miles, around 2 hours. Skips Bay Area traffic entirely, though it is the longest drive of the four.
Flying private? We also meet guests at the FBOs at STS and Napa County Airport (APC). See our Sonoma County Airport car service page for more on flying into STS.
At a Glance
Location
25 W. Grant Street, Healdsburg
Style
Queen Anne Victorian inn, 10 rooms
Closest Airport
Santa Rosa Airport (STS), about 20 minutes
Good to Know
Check-in 2 to 4:30 p.m., check-out 11 a.m. Limited parking behind the inn, free street parking on Grant Street.
Pickup at 10:00 a.m. at the front of the inn on Grant Street.
Your chauffeur meets you at the front of the inn on Grant Street. The day below fits a six-hour tour, and extra time can be added by the hour.
About 20 minutes away. Estate Pinot Noir, Chardonnay and some of California's oldest Sauvignon Blanc vines, on Westside Road. The Estate Flight is $25; allow 60 to 90 minutes. By appointment, Monday to Saturday.
About 15 minutes away. A bakery café and a Healdsburg tradition since 1923, a short walk from the plaza. Open daily from 7:30 a.m. Prefer a picnic? We can arrange a catered picnic at a winery that allows one; the cost is quoted when you book.
About 15 minutes away. Block 21 Cabernet and Henry's Blend from five family ranches, poured in Geyserville. The Discover Estate Wine Flight is $30. Thursday to Monday; walk-ins welcome for the flight.
About 15 minutes away. Sauvignon Blanc, Dry Chenin Blanc and Zinfandel from the first new winery built in Dry Creek Valley after Prohibition. Guided tastings run $30 to $50. Reservations strongly encouraged.
About 15 minutes away. Back by 4:00 p.m., six hours after pickup.
Adds about an hour. Estate Pinot Noir and Chardonnay from a far Sonoma Coast vineyard, poured in downtown Healdsburg. Discover Hirsch, a communal tasting of four wines, is $45. By appointment only.
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.
See every winery we cover, region by region, on our Sonoma County wineries page.
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.
Airport transfers are priced by distance when you book, with gratuity included. Larger groups travel in more than one vehicle. Tasting fees are separate and paid directly to each winery.
Sonoma County Airport (STS), about 11 miles or roughly 20 minutes by car. Oakland (OAK) is next, at about 1 hour 45 minutes.
About 11 miles, or roughly 20 minutes by car. STS is a small, easy airport, and the drive avoids Bay Area traffic.
It is on West Grant Street on the north side of Healdsburg, a short drive from Healdsburg Plaza.
Airport transfers are priced by distance when you book online, and gratuity is included, so you see the full fare before you pay.
Your chauffeur tracks your flight and texts you before departure and again on landing to confirm the pickup spot. Up to 60 minutes of waiting is included. Meet and greet at baggage claim is available for $50.
Yes. Six-hour private wine tours start at the inn, from $750 plus 20% gratuity in an Elite Luxury SUV for up to 6 guests, or from $1,350 plus gratuity in a Jet Sprinter for up to 9. Tasting fees are paid directly to each winery.
Reserve 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.
Book Your Airport Ride or Wine Tour
Reserve online in minutes. For an airport pickup, add your flight and your chauffeur will track it and text you on landing. For a wine tour, your plans don't need to be final: your chauffeur will email you first, then build the itinerary and make the winery appointments. Prefer to talk? Call our concierge at 888-291-2328.
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