Healdsburg Wine Tours with a Private Chauffeur

• Sonoma County Airport (STS), Santa Rosa: About 20 minutes. The closest airport, with nonstop flights from much of the West. Approx. 11 miles.
• Calistoga: About 30 to 35 minutes. Over the hills on Highway 128 through Knights and Alexander Valleys. Approx. 24 miles.
• Napa (city): About 1 hour to 1 hour 15 minutes. Approx. 50 miles.
• San Francisco International (SFO): About 1 hour 45 minutes, longer at busy times. Approx. 82 miles across the Golden Gate.

Three wineries and a long lunch, mixing Dry Creek Valley, downtown and Alexander Valley. Every day is planned around you; this is a starting point.

• 10:00 · Pickup at your Healdsburg hotel
• 10:15 · Ridge Lytton Springs (About 10 minutes) Old-vine Zinfandel at the straw-bale winery. The estate tasting runs about 75 minutes.
• 11:45 · Lambert Bridge (About 15 minutes) A seated tasting of small-lot Bordeaux varieties on West Dry Creek Road.
• 1:15 · Lunch at Troubadour, downtown (About 20 minutes) The daytime bakery and sandwich side of a Michelin-starred kitchen, a block from the plaza. Prefer a picnic? We can arrange one at a winery that allows it.
• 2:45 · Jordan, Alexander Valley (About 15 minutes) A Taste of Jordan at 3 p.m., about 45 minutes, by appointment. The winery asks guests to arrive 15 minutes early.
• 4:00 · Back at your hotel (About 15 minutes) Six hours from pickup. Downtown tasting rooms such as LIOCO stay open into the evening if you would like one more on foot.

Downtown, Walkable from the Plaza (34)

More than thirty tasting rooms sit within a few blocks of the plaza, several of them open into the evening. An easy start or finish to a day in the valleys.

Arnot-Roberts, Blanchard Family Wines, BloodRoot, Centennial Mountain, Ceritas, Cobb Wines, Coyote Sonoma, Ehret Family Winery, Enkidu Wines, Ernest Vineyards, GrapeSeed, Gros Ventre Cellars, Hirsch Vineyards, Idlewild, Leo Steen Wines, LIOCO, Longboard Vineyards, Marchelle Wines, Marietta Cellars, Marine Layer, Martha Stoumen, Portalupi Wine, Ramey Wine Cellars, Rockpile Vineyards, Sapphire Hill, Selby Winery, Siduri, Spicy Vines, Stressed Vines Cellars, Meeker, Truett Hurst, Valette Wines, VML, Seghesio Family Vineyards

Dry Creek Valley (76)

Old-vine Zinfandel country, ten minutes northwest of the plaza, with family wineries along Dry Creek and West Dry Creek Roads.

A. Rafanelli, Aesthete, Aldina Vineyards, Amista Vineyards, Amphora Winery, BACA, Bella Vineyards, Breathless, BuonGuido, Capo Creek Ranch, Cartograph, CAST Wines, Chateau Diana, Comstock Wines, Convene by Dan Kosta, DaVero Farms & Winery, David Coffaro, De La Montanya, DOT Wines, Dry Creek Vineyard, Dutcher Crossing, F. Teldeschi, Ferrari-Carano, Flambeaux Wine, Flanagan Wines, Forth Vineyards, Frick Winery, Gregory James Wines, Guadagni Family Wines, Hawley Winery, Homefire, Kokomo Winery, Lambert Bridge, Martorana, Mascarin Family Wines, Mauritson, Mazzocco, Michel-Schlumberger, Mill Creek Winery, MoniClaire Vineyards, Mounts Family Winery, Nalle, Optima Winery, Orsi Family Vineyards, Overshine, Papapietro Perry, Passalacqua, Pasterick Wines, Pearce Family Wines, Pedroncelli, Peterson Winery, Pezzi King, Preston Farm & Winery, Quivira, Raymond Burr Vineyards, Reeve, Ridge Lytton Springs, Rued Winery, Saini Vineyards, Seaton Family Vineyards, Simoncini Vineyards, Smith Story, Solo Nostro, Stephen & Walker, Talty Winery, Terra Amata Vineyards, Tongue Dancer Wines, Trattore Farms, Unti Vineyards, van Z Vineyards, Wayfarer, We Know Jack, West Wines, Williamson Wines, Wilson Winery, Zichichi Family Vineyard

Alexander Valley & Rockpile (35)

Broad, warm and quieter, northeast of town toward Geyserville, and known for Cabernet Sauvignon.

ACTA, Alexander Valley Vineyards, Bannister Wines, Bedarra Vineyards, Bellacana Vineyards, Carpenter Wine, Crux Winery, deLorimier Winery, Francis Ford Coppola Winery, Garden Creek, Hafner Vineyard, Hanna Winery, Hawkes, Jordan Winery, Lampson Family Wines, Lancaster Estate, López Family Vineyards, Medlock Ames, Mercury Wine, Munselle Vineyards, Pastori Winery, Pech Merle, Ramazzotti Wines, Rancho Maria, Robert Young, Silver Oak Alexander Valley, Skipstone, Soda Rock Winery, Starlite Vineyards, Stonestreet, Stuhlmuller Vineyards, Trentadue, Trione, Vérité, Zialena

Russian River Valley, Westside Road & Chalk Hill (29)

Pinot Noir and Chardonnay along the river south of town, where Westside Road holds some of the valley's most storied names.

Aperture Cellars, Bacigalupi Vineyards, Christopher Creek, Copain Wines, Due Ruscelli, Flowers, Foppiano Vineyards, Gary Farrell, Gracianna, Harper's Rest, Ketcham Estate, Limerick Lane Cellars, MacRostie, Matrix Winery, Merriam Vineyards, Moshin Vineyards, Porter Creek, Rochioli, Rootdown Wine Cellars, Thomas George Estates, Twomey Healdsburg, Viszlay Vineyards, Williams Selyem, Acaibo, Chalk Hill Estate, Davis Bynum, J Vineyards, Rodney Strong, ROWEN Wine Company

Explore the appellations: Dry Creek Valley, Alexander Valley, Russian River Valley, Chalk Hill, Rockpile, Knights Valley, all of Sonoma County. Winemakers with Healdsburg ties: Jesse Katz, Aperture Cellars, Michael Browne, CIRQ, and more on our Napa & Sonoma winemakers page.

We collect guests at every hotel in town. Each links to a page with airport drive times and a suggested tour from the door.

• Montage Healdsburg: 130 bungalow-style rooms and suites on a vineyard and woodland estate just outside town, opened December 2020. Two Michelin Keys.
• SingleThread Inn: Five rooms above the three-star restaurant on North Street; inn guests are guaranteed a dinner reservation. Three Michelin Keys, Relais & Chateaux.
• Appellation Healdsburg: Charlie Palmer's 108-room resort in the North Village, opened September 2025, with gardens, a citrus orchard and working vineyards.
• The Madrona: Formerly Madrona Manor: 24 rooms across an 1881 mansion and gardens on eight hillside acres off Westside Road. Two Michelin Keys.
• The Cottages at Little Saint: Four cottages by designer Ken Fulk beside Little Saint, with a heated pool. One Michelin Key.
• Hotel Healdsburg: 55 rooms on the west side of the plaza, home to Dry Creek Kitchen, a spa and a pool by an olive grove.
• Harmon Guest House: A 39-room boutique hotel just off the plaza, with a rooftop bar looking toward Fitch Mountain.
• h2hotel: A 36-room LEED Gold hotel with a living roof and Spoonbar downstairs.
• Duchamp Healdsburg: An adults-only hotel on Foss Street, rebuilt and reopened in April 2026 with 20 suites around a pool courtyard.
• Healdsburg Inn on the Plaza: Twelve rooms in the 1901 Kruse Building directly on the plaza.
• Hotel Trio: An all-suite hotel on Dry Creek Road with full kitchens in every suite; practical for families and longer stays.
• The Lodge at Healdsburg: A Tapestry Collection hotel on Grove Street with courtyards, fireplaces and a heated pool.
• Dry Creek Inn: A 103-room hotel at the gateway to Dry Creek Valley, renovated in 2022.
• The Ruse: Formerly the Honor Mansion: an 1883 Victorian on four acres at the edge of town, close to Dry Creek Valley.
• Camellia Inn: An 1871 Victorian bed and breakfast two short blocks from the plaza.
• Grape Leaf Inn: A 1900 Queen Anne Victorian on Johnson Street with a spa and gardens.
• Calderwood Inn: A 1902 Queen Anne Victorian bed and breakfast with gardens first laid out with Luther Burbank's help.
• Rockhouse Suites: Two suites steps from the plaza, from the family behind Rockpile Vineyards.
• Fairview Inn & Suites: A simple, good-value inn at the south end of Healdsburg Avenue, near Westside Road.
• Geyserville Inn: A family-run 42-room country inn in Geyserville, at the north end of Alexander Valley.

See all Sonoma County hotels.

For a town of its size, Healdsburg eats remarkably well. Michelin distinctions below are from the guide's current Healdsburg listing.

• SingleThread (Healdsburg), Three Michelin Stars (retained in the 2026 California guide): Kyle and Katina Connaughton's kaiseki-inspired tasting menu, drawn from their own farm. The five-room inn sits upstairs.
• Troubadour (Healdsburg), One Michelin Star (first awarded 2026): A bakery and sandwich shop by day; in the evening, Sean and Melissa McGaughey's tasting menu. A good lunch stop on a tour day.
• Cyrus (Geyserville), One Michelin Star (2026 guide listing): Douglas Keane's reborn Cyrus, in a concrete-and-glass building among Alexander Valley vines. Dinner Thursday to Sunday.
• Valette (Healdsburg), Michelin Guide selected: Dustin Valette's modern American cooking with French influences, on Center Street.
• Barndiva (Healdsburg), Michelin Guide selected: Seasonal Californian cooking built on local produce, with a garden for warm evenings.
• Dry Creek Kitchen (Healdsburg), Michelin Guide selected: Charlie Palmer's long-running dining room inside Hotel Healdsburg, overlooking the plaza.
• Diavola (Geyserville), Michelin Guide selected: Wood-fired pizza and pasta in Geyserville; an easy lunch on an Alexander Valley day.
• Little Saint (Healdsburg): A plant-based restaurant, cafe and bar at 25 North Street, beside the Cottages at Little Saint.
• Hazel Hill (Montage Healdsburg): Montage Healdsburg's signature restaurant, with seasonal Californian cooking.

We drop you at the door and collect you after dinner, so no one has to drive.

• Harvest, roughly August to October: The busiest and most beautiful stretch, with crush under way at many wineries. Book appointments and weekends early.
• Winter Wineland, mid-January: The Wine Road's winter weekend of tastings across northern Sonoma County (held January 17-18 in 2026).
• Barrel Tasting, March: The Wine Road's long-running barrel weekend (the 48th was March 7-8, 2026; the 49th is listed for March 5-7, 2027).
• Healdsburg Jazz Festival, June: Ten days of concerts around town, including on the plaza (June 12-21 in 2026).

Combining Napa Valley and Healdsburg

From Calistoga it is about half an hour over Highway 128 to Healdsburg, so a day that pairs a winery at the top of Napa Valley with two in Alexander or Dry Creek Valley works well, especially in a seven or eight hour tour.

From Yountville or Napa, Healdsburg is an hour or more each way. We usually suggest giving each region its own day; if you would like to see both, we will plan the route so the time is spent tasting, not driving.

See Calistoga wineries and Napa Valley wine tours.

Do Healdsburg wineries require appointments?

Many do, and some, such as Jordan and A. Rafanelli, are appointment only. Others, including several downtown tasting rooms, welcome walk-ins when space allows. We confirm each appointment before your day.

Can you book the tastings for us?

Yes. Tell us which wineries you would like to visit, or the kinds of wine you enjoy, and we arrange the appointments in advance. Tasting fees are paid directly to each winery.

How many wineries can we visit in a day?

Three is the right pace for a six-hour day with lunch. A fourth is possible if one stop is a short downtown tasting, or if you add time.

How large a group can you take?

Our Lincoln Navigator and Cadillac Escalade carry up to six guests. For groups of up to nine, we use an Executive Luxury Van or Jet Sprinter.

Can you pick us up at Santa Rosa airport?

Yes. Charles M. Schulz-Sonoma County Airport (STS) is about twenty minutes from Healdsburg. We track your flight and meet you at the curb, and we also meet private aircraft at both STS FBOs.

Will you collect us from our hotel?

Yes. Every tour starts and ends at your door, whether you are staying at Montage Healdsburg, on the plaza, or at a rental in the valleys.

Can we bring children?

Children are welcome in our vehicles, and child seats are available on request. Some wineries, Jordan among them, admit guests 21 and over only, so we plan the day around who is traveling.

Can you bring our wine back to the hotel?

Yes. Your chauffeur loads and handles any bottles or cases you buy along the way.

What is your cancellation policy?

Cancel at least 24 hours before pickup for a full refund. Within 24 hours of pickup, the reservation is non-refundable.