20 Best Healdsburg Wineries I Actually Go Back To Again and Again

Healdsburg is my favorite place to go wine tasting in California. Full stop.

I live in San Francisco, which means I can wake up, throw on a sundress, grab coffee for the road, and be in Sonoma County wine country before noon. I’ve gone up for girls trips, anniversaries, last-minute escapes, and once just because the weather in Dry Creek Valley looked too good to waste.

I’ve lost track of how many times I’ve visited Healdsburg. What I haven’t lost track of are the details. The bookstore cats are always hiding among the shelves. The way the whole town turns gold and red in October and how the fog lifts slowly off the vineyards in Russian River Valley while you’re holding your first glass of the day.

I first wrote this post in 2018. Since then, wineries have closed, moved, renovated, added new tasting rooms, or completely shifted their vibe. So this is your fully updated 2026 guide to the best Healdsburg wineries, based on years of actually going.

If you’re planning a wine tasting weekend in Sonoma, here’s exactly where I’d send you.

First: Understanding Healdsburg Wine Country

Healdsburg sits where three major AVAs meet and there’s a lot happening here. Heck, Russian River Valley has more different soil types than all of France, and you can actually taste the differences when you do a flight here.

• Russian River Valley: cooler climate, think elegant Pinot Noir, structured but balanced Chardonnay and lots of fog influence from the river valley.
• Dry Creek Valley: warmer and more rugged with bold reds. Zinfandel thrives and you often get great vineyard views.
• Alexander Valley: Cabernet Sauvignon country. If you love Cabs but don’t want to visit Napa, come here. 

Each valley produces very different wines. When you’re wine tasting in Healdsburg, you’re usually bouncing between at least two of these valleys without even realizing it. This is why I keep coming back. 

My Favorite Healdsburg Wineries For Wine Tasting In The Vineyards

If you want vineyard scenery and that classic Sonoma wine country backdrop, start here.

Banshee Wines 

Banshee is no longer downtown, they moved into the former Foley Sonoma estate and the new setup is honestly better than the old tasting room ever was.

You’re fully in the vineyard now with big windows, a fireplace, records playing. It feels cool without trying too hard. Very millennial but grown up. 

Plus, the view is one of the best in the valley. You’re staring straight out at vines, not a parking lot. I even have a painting of their vineyards hanging in my apartment. 

They also offer rotating lunch boxes, which makes this one of the stronger Healdsburg wineries with food right now. I love this because it means you can make this a full stop instead of squeezing in food somewhere else. The menu changes often, but it leans into elevated comfort food from our childhood. 

Their Pinot Noir is some of the best in the valley making this one of the best wineries in Healdsburg if you want scenery and a relaxed tasting experience in one stop.

Lancaster Estate

We still jokingly call this the Game of Thrones winery because of the lion logo. Lancaster. Lannister. Close enough.

Lancaster Estate sits in Alexander Valley and makes beautiful Cabernet Sauvignon. The rocky soils here really show up in the structure of their Cabs and Bordeaux blends. 

What I love about Lancaster, beyond the wine, is the whole experience. First, the fall foliage. If you go in October or November it is unreal. Bright red vines…golden leaves. It feels cinematic and the girls and I always sneak into the vineyards to snap photos. 

Second, the wine cave with a concrete egg. You have to ask to see it. It’s dramatic, cool, and moody, and the first time I walked into it with my friends we just stood there like, okay, this is the moment.

They recently added a new indoor member tasting area with cozy chairs and a view of Mount Saint Helena, which makes winter visits even better since you may see the mountain covered in snow like we did. But I still love sitting outside under the trees when it’s warm and stretching a tasting into a two-hour hang.

If you love Cabernet Sauvignon, this is one of the best Healdsburg wineries you can visit.

Chalk Hill Estate

Chalk Hill has one of the best views in Sonoma. That’s not an exaggeration.

You’re up high, looking out over rolling vineyards in every direction. The patio is incredible, but the indoor seating is beautiful too if the weather turns.

They’re known for Chardonnay, but I’ve swapped in Pinot Noir or Sauvignon Blanc before and the staff has always been accommodating. I also adore their Syrah, which most recently was blended with Viognier for a slight floral taste. 

They also offer an epic Jeep estate tour that takes you across their vineyard property, which gives you a much better sense of how massive it really is. There’s even a hidden church back there! 

If you’re building a list of Healdsburg wineries with a view, Chalk Hill belongs on it.

Gary Farrell Vineyards & Winery

If I had to choose a singular favorite near Healdsburg, Gary Farrell might win. This is a good one to tack onto a Guerneville trip, too. 

They helped define Russian River Valley Pinot Noir before the AVA even existed. Their first Pinot came from Rochioli Vineyards, which is now basically legendary in Sonoma. Theresa Heredia crafts stunning single-vineyard Pinot Noir and Chardonnay that really showcase terroir. 

The patio view is gorgeous, but the wine is the reason to go. If you care about Pinot Noir, this is one of the best wineries in Healdsburg.

Reeve Winery

Reeve feels tucked away in the best way. It’s out in Dry Creek Valley, surrounded by trees and vines, and the tasting room sits inside a small barn. I grew up around farmland in Wisconsin, so something about Reeve always feels familiar and grounding to me.

Their Rosé of Pinot Noir is one I’ve brought home more than once. It’s also one of the rare Healdsburg wineries that are kid-friendly and dog-friendly.

If you want something romantic but relaxed, this is a great choice.

Flowers Winery Healdsburg

Everything about my visit to Flowers felt dialed in. You’re greeted with rosé at the entrance, then seated outside with a view of flowering vineyards and Mount Saint Helena in the distance. It was one of those perfect wine country afternoons where you don’t want to check your phone.

Flowers pioneered Pinot Noir and Chardonnay from the Sonoma Coast ridges, and their tasting room reflects that focus.

Their in-house chef creates pairings that genuinely enhance the wine. I still think about the crisp Chardonnay paired with gougère and wild fennel pollen. It worked.

If you’re looking for elevated Healdsburg wineries with food, this is one of the strongest tasting experiences in town right now.

Rodney Strong Vineyards 

Rodney Strong is technically closer to Windsor, not Healdsburg proper, but it’s such a quick drive that I always mentally group it into my Healdsburg wine tasting weekends.

They have a beautiful, modern tasting room that feels open and polished without being stuffy. The property itself is gorgeous, especially in summer when everything is green and glowing.

What really stands out here are their events. Last year I went to one of their pizza night evenings and it was packed in the best way. Wood-fired pizza, live energy, wine flowing, everyone relaxed and leaning into summer. I also attended one of their garden parties, which felt more elevated but still fun. It didn’t feel corporate. It felt like people genuinely enjoying being outside with good wine.

Rodney Strong makes excellent wine across the board, from expressive Chardonnay to bold Cabernet Sauvignon, and they’re one of those wineries that does scale well without losing quality.

If you’re planning a summer wine country weekend and want something with built-in energy, add Rodney Strong to your Healdsburg itinerary. It’s close enough to count and good enough to justify the drive.

DaVero

DaVero focuses on “growing what belongs here.” Mediterranean varietals like Primitivo and Vermentino thrive in their vineyard. Everything is biodynamically farmed.

You walk the property. You learn something. The wine feels connected to the land. If you’re ready to branch out from Pinot Noir and Cabernet Sauvignon, this is where to do it.

Coursey Graves Winery

Coursey Graves does mountain-grown Chardonnay, Pinot Noir, Cabernet Sauvignon, and Syrah flight covers a lot of ground, which makes this an easy pick if you’re tasting with a mixed group. There’s something for everyone without it feeling random.

What really sets them apart is the optional chocolate pairing. Wine is meant to be paired with food to highlight different flavor notes, and the chocolate flight adds a fun, elevated twist without feeling gimmicky.

Aperture Cellars

Aperture blends photography and wine in a way that actually works. The tasting room features large-scale photographs by Andy Katz, and the skylight is shaped like a camera shutter opening. It’s dramatic without being cheesy.

The patio views are beautiful. The wines are bold. The whole experience feels immersive.

Ferrari-Carano Winery

Ferrari-Carano is where I go when I want chateau vibes. It has gardens, fountains, big Dry Creek Valley views that are extra beautiful in autumn. 

I love coming here in the morning and sitting outside with a tasting that isn’t rushed. If you’re using the Foley wine family membership hack, this pairs perfectly with Banshee or Chalk Hill and keeps tasting fees down.

If you’re coming for lunch, grab sandwiches from the General Store on the way and picnic in the garden. Their Fumé Blanc is especially good on a warm day. 

Scenic, polished, easy to love.

Brulium Wines

Brulium is small production, around 1,000 cases per year, focusing heavily on single-vineyard Pinot Noir. Kerith Overstreet works closely with growers, and every bottle lists the vineyard it came from. It feels intentional and respectful.

If you love small-lot Pinot, add this to your list.

Medlock Ames

Medlock Ames at Bell Mountain Ranch feels more immersive than your standard tasting room.

We started with a small walking tour of the property, strolled through the vineyards, and peeked into their production area before settling into a seated tasting paired with cheese and crackers. It feels intentional and connected to the land, not just a bar and a pour.

Their soils are heavy clay loam and relatively shallow, which produces structured, expressive Cabernet Sauvignon, but honestly everything on the tasting menu tends to be solid. If you’re interested in organic farming and a deeper look at how wine is actually made, this is a strong stop to add.

Top Downtown Healdsburg Tasting Rooms I Love

If you don’t want to drive all day, downtown Healdsburg makes it easy to walk between tasting rooms.

Siduri

Siduri is still one of my favorite tasting rooms in town.

Rustic-chic inside with big windows that open on warm days. There’s a window seat I’ve claimed more than once while slowly working through a Pinot Noir flight.

They focus heavily on Pinot from Russian River Valley and beyond. If Pinot is your thing, you could easily spend your whole tasting here and be happy. And when you’re done, you’re already downtown for dinner.

Cartograph Wines

Cartograph feels thoughtful and unique. The tasting room has a clean, slightly science-forward feel. Sometimes they serve wine in beakers, which is subtle but fun. They focus primarily on Pinot Noir and aromatic whites inspired by Alsace.

It’s husband-and-wife run, sustainability is baked into everything, and it always feels calm inside.

This is an easy add to a downtown wine tasting day.

VML (Downtown + Dry Creek Valley)

VML used to require a drive out to Dry Creek Valley. Now they have a downtown tasting room too, which I love because it gives you options.

Their wines are creative. I’ve seen flavor notes like mushroom and marshmallow show up on a tasting menu before, and somehow it works.

If you’re tired of predictable wine and want something with personality, VML is a fun stop.

Prestige Healdsburg Wineries Worth The Effort

These aren’t casual walk-in tasting rooms. These are the names collectors talk about and the ones that require more planning ahead of time. All wineries require reservations but these are ones your wine friend casually drops into conversation so they’re worth it. 

If you’re building a serious Healdsburg wine tasting itinerary, these wineries deserve a look.

A. Rafanelli Winery

A. Rafanelli Winery is one of those places you have to plan for. They’re family-run, appointment-only, and deeply rooted in Dry Creek Valley.

Their Zinfandel and Cabernet Sauvignon are classic, structured, and age-worthy. There’s no flashy tasting room here and it’s about the wine and the family legacy.

If you want a true old-school Sonoma County experience, Rafanelli delivers it.

Rochioli Vineyards

Rochioli Vineyards is legendary in Russian River Valley Pinot Noir history.

Gary Farrell sourced fruit from Rochioli Vineyard back before Russian River was even an official AVA, and today the name still carries weight. Their Pinot Noir is refined, layered, and distinctly Russian River in character.

Reservations can be competitive, but if Pinot is your thing, this is one of the most important vineyards in the valley.

Silver Oak Alexander Valley

Silver Oak’s Alexander Valley estate absolutely belongs on this list, even though they also have a Napa tasting room. Their Cabernet Sauvignon is iconic. Structured, bold, polished. The tasting room itself is sleek and impressive without feeling overdone.

If you want a vertical tasting experience or you’re traveling with someone who loves classic California Cab, Silver Oak is a strong pick.

Jordan Winery

Jordan Winery feels European in its approach.

Inspired by French techniques, Jordan focuses on balanced Cabernet Sauvignon and elegant Chardonnay from Alexander Valley. Their estate tour is one of the more immersive tasting experiences in Healdsburg wine country, especially if you appreciate food pairings and a slower, more curated visit.

It’s refined without being intimidating. Oh, and their road leading up to the tasting room has amazing fall colors during autumn. 

Lambert Bridge

Lambert Bridge sits in Dry Creek Valley and feels rustic in the best way.

It’s romantic, garden-filled, and incredibly welcoming. They’re known for small-lot wines and thoughtful food pairings, and they’re also dog-friendly, which I always appreciate.

This is a great choice if you want a relaxed but elevated tasting experience that still feels connected to the land.

2 Day Healdsburg Wine Tasting Itinerary (With My Money-Saving Hack)

This is how I actually plan a weekend in Healdsburg. Not ten wineries crammed into one day but instead a smart mix of scenic vineyard stops, walkable downtown time, and good food.

And before we get into it, here’s the hack that makes this whole itinerary way more affordable.

The Foley Wine Family Hack (Free Wine Tastings)

If you join one winery that’s part of the Foley wine family, you can wine taste for free at other participating wineries within the group. That includes places like Banshee, Chalk Hill, Lancaster, and Ferrari-Carano, among others across the state. 

So instead of paying $35 to $55 per tasting at multiple spots, you join one wine club and suddenly your Healdsburg wine tasting weekend becomes dramatically more affordable.

That’s how we do it.

We use the savings on:

• Buying bottles we actually love (I always bring home 1-2 a trip!)
• Staying somewhere nicer
• Better dinners
• Not stressing about the tasting fees

Now here’s how I’d structure a two-day Healdsburg wine weekend.

Day 1: Vineyard Views + Downtown Healdsburg

Drop your bags at the new Appellation Hotel in downtown Healdsburg. It’s new and so beautiful. I just did a girls trip here and we loved the large rooms, free coffee in the morning, rooftop bar, vineyard views, and late night hot tub. 

Don’t unpack, just head straight to your first tasting.

Late Morning: Banshee (In The Vineyards)

Start at Banshee’s new vineyard location. This used to be the old Foley Sonoma estate, and now it’s one of the best wineries with a view in the area.

Fireplace inside. Records stacked on the shelves. Big vineyard views outside. It’s cool without trying too hard.

If you’re using the Foley wine family membership, this tasting can be complimentary. Sit for a bit. Ease into wine country mode.

Midday: Ferrari-Carano (Chateau Energy)

Next, drive over to Ferrari-Carano in Dry Creek Valley. It’s now part of the Foley wine family too, which makes pairing these two stops smart.

Sit outside at the chateau. It feels almost Napa-ish but without the Napa attitude.

You can:

• Bring a small packed lunch to eat in the garden
• Stop at the General Store on the way for something easy, I love their sandwiches
• Or just snack lightly and focus on the wine

Their Flume Sauvignon Blanc is great on a warm day. 

Afternoon: Downtown Healdsburg Walk + Happy Hour

Head back into town and park the car for the rest of the day. Start with a downtown tasting at Siduri or VML. Then walk around Healdsburg Plaza and pop into shops. You can’t miss Copperfield Bookstore, always good finds here and I love the shop cats. 

For happy hour:

• Grab a drink at PizZando if you want something casual ($5 happy hour glasses of wine!)
• Or head to Little Saint for cocktails and food

Then head back to Appellation. You can:

• Have dinner there if you’re staying in
• Or soak in the hot tub and fully lean into wine country relaxation

Day 2: Bordeaux + Chardonnay + Valley Views

Start your morning slow at the hotel, it’s beautiful. 

Breakfast: Plank

Go to Plank for breakfast and coffee. Do not skip the biscuits. I repeat, do not skip the biscuits! Get a caramel latte or coffee, sit for a bit, and reset your palate.

Now you’re ready for structured wines.

Late Morning: Lancaster Estate (Alexander Valley)

Head to Lancaster first and focus on their Bordeaux-style wines. This is where you shift into Cabernet Sauvignon and blends.

Ask about the cave. If you’re there in fall, the foliage alone is worth the drive. The new indoor tasting space makes winter visits cozy, but I still love sitting outside when it’s warm.

This is a more structured tasting experience, so keep it to one solid flight and take your time.

Midday: Chalk Hill Estate (Views + Chardonnay)

Next, drive to Chalk Hill, about 5 minutes down the road. 

Sit outside if you can. The views across the valley are some of the best in Sonoma County. This is where you switch into Chardonnay or explore their Bordeaux varietals.

Optional Add-Ons Before Heading Back To The City

If you’re driving back to San Francisco and have energy left, you have two strong options.

Rodney Strong (Closer To Windsor, Worth It)

Rodney Strong is technically closer to Windsor, but it’s a quick drive from Healdsburg.

Their summer events are fantastic. I went to their pizza night last year and one of their garden parties, and both had that perfect wine country summer energy. Wood-fired pizza, people lingering, glasses constantly refilled.

It’s a great final stop if you want something lively before heading home.

Gary Farrell (Pinot Power Move)

If you want to end on a high note and you love Pinot Noir, stop at Gary Farrell.

Russian River Valley Pinot here is serious. The views are beautiful, but this stop is about tasting terroir differences and understanding why this valley is so respected.

It’s a strong way to close out a weekend.

Healdsburg Wine Tasting FAQ

These are the questions I get in my DMs every single time I post from Healdsburg.

Do You Need Reservations For Healdsburg Wineries?

Yes. Almost always.

Most Healdsburg wineries require advance reservations now, especially in Russian River Valley, Dry Creek Valley, and Alexander Valley. Even downtown tasting rooms often book up on weekends.

If you’re visiting during harvest season or summer, book at least a week in advance. Prestige wineries like A. Rafanelli, Rochioli Vineyards, and Silver Oak can require even more planning.

Don’t wing it. You’ll spend half your day refreshing OpenTable and calling tasting rooms.

What Is The Best Time Of Year To Visit Healdsburg?

There isn’t a bad season, but each one feels different.

Fall (September through November) is my personal favorite. The vineyards turn bright red and gold, harvest is happening, and the energy in Sonoma County wine country feels electric.

Summer is warm and lively. Perfect for patio tastings in Dry Creek Valley and events like Rodney Strong’s pizza nights.

Winter is quieter and cozier. You’ll get more intimate tasting experiences, especially indoors at places like Lancaster Estate.

Spring brings wildflowers and softer green vineyard views, especially in Russian River Valley.

If you want fewer crowds, skip peak summer Saturdays.

Is Healdsburg Better Than Napa?

This is subjective, but for me, yes.

Healdsburg feels smaller, more walkable, and less corporate. You can taste Russian River Valley Pinot Noir in the morning, explore Dry Creek Valley in the afternoon, and walk to dinner at night.

Napa has prestige and scale. Healdsburg has personality and range.

If you love Cabernet Sauvignon but don’t want Napa pricing and traffic, Alexander Valley is a strong alternative.

How Many Wineries Should You Visit Per Day?

Two, maybe three.

Anything beyond that and your palate gets tired. You stop tasting and start just drinking.

A good Healdsburg wine tasting day balances:
• One scenic vineyard stop
• One structured tasting experience
• One relaxed downtown tasting room

Leave space for food and wandering the plaza.

Are There Healdsburg Wineries With Food?

Yes, and it’s gotten much better over the years.  Most will offer some sort of cheese plate but these are the best options. 

• Banshee offers rotating lunch boxes at their vineyard location.
• Flowers Winery has a strong chef-driven pairing program.
• Jordan Winery is known for curated food and wine experiences.
• Lambert Bridge often incorporates thoughtful small bites into tastings.
• Rodney Strong has special pizza nights

If food is important to you, plan ahead and book a dedicated pairing experience rather than assuming every winery offers full meals.

What Is The Difference Between Russian River Valley, Dry Creek Valley, And Alexander Valley?

They’re all close to Healdsburg, but they produce very different wines.

Russian River Valley is cooler and known for elegant Pinot Noir and balanced Chardonnay.

Dry Creek Valley is warmer and more rugged. Zinfandel thrives here, and vineyard views are dramatic.

Alexander Valley is Cabernet Sauvignon country. Warmer climate, structured reds, big valley views.

One of the reasons Healdsburg is such a strong wine tasting destination is that you can experience all three valleys in one weekend without driving far.

Is Healdsburg Good For A Girls Trip Or Romantic Weekend?

Both.

I’ve done girls trips where we stayed walking distance to the plaza and bar hopped after dinner. I’ve also done quiet anniversary weekends where we prioritized vineyard tastings and slow mornings.

Because Healdsburg is compact, you can build the weekend around your vibe instead of fighting traffic the entire time.

Healdsburg Winery Map

I made you a Healdsburg Wineries Map on Google Maps to save or use when helping you plan! When we decide what tasting rooms to visit in a day, we make a short Healdsburg wineries list and then look at them on a map to decide what’s near each other so we should group them together.

Healdsburg Is Worth The Wine Trip

I’ve done Napa. I’ve done Paso. I’ve done Santa Barbara. I even love Anderson Valley. 

I still choose Healdsburg and the Dry Creek vineyard row. 

It feels approachable but serious… small town but world-class wines. You can drink Russian River Valley Pinot in the morning, Alexander Valley Cabernet Sauvignon in the afternoon, and walk to dinner that night.

Folks will always be kind, treats you like family, and you can find budget meals or Michelin-star dining pouring the best wines in Healdsburg. Can’t beat that.