Imagine a place where wine flows from every corner…where there’s so many different wine tasting rooms that anybody can find their ideal atmosphere…where lodging, shops, and restaurants are right next door and within walking distance…and imagine it’s all affordable! Paradise you ask? No…but its close. Its Healdsburg, California.

In the heart of Sonoma County and just an hour’s drive north of San Francisco lies a sweet little gem of a town called Healdsburg. At the center is Healdsburg Plaza where you’ll find over a dozen different wine tasting rooms all within a four-block by four-block radius. Healdsburg has the feel of Sonoma but with less tourists (although many locals like to go here too, so it can get a little crowded during holidays and weekends.)

The Traveling Wino and Mr. Wino happily visit Healdsburg California

Visitors might be attracted to Sonoma because its a shorter drive from San Francisco and its next to Napa. But we actually prefer the slightly longer trip to Healdsburg because you end up with a scenic drive to get there. And if you’re a sucker for wine tasting out among the vineyards (like we are…), there are a half-dozen rural wineries dotted along Highway 101 and the surrounding area, so you can spend a whole day visiting these as well.

If you’re a shopper or “foodie”, you will love Healdsburg even more because restaurants and cafes line the street and there’s a wide variety of menus and price points to suit your taste. The shopping is varied as well. You can find retail shops that have higher-end merchandise or you can opt for a lower-price boutique.  There’s also several art galleries near the plaza for the cultured folk too.

The best part about Healdsburg for most visitors is that they can experience a day of wine tasting without having to worry about finding a designated driver. Because there’s more than enough tasting rooms in town, an afternoon of wine tasting can be enjoyed by simply walking from place to place. Several inns and bed and breakfasts are in walking distance as well. However, keep in mind that they fill up quickly and many can be a bit expensive…but thankfully there’s still a couple that are reasonably priced. For rural wine tasting, there’s a wine tour operator located right in town that can take you on tours, and if you want an in-town guide, a walking tour operator is there too.

If all of these reasons weren’t enough to draw us to Healdsburg, we found the wines to be just as varied as the restaurants, shopping, and wine tasting rooms. Some tasting rooms are taking a cue from their more expensive “cousins” in Napa and Sonoma and charging more for fewer tastings. But if that is the case, usually the wines will be great quality too.

In our visits to Healdsburg we “bellied up” to the wine tasting bars of a few places and found our experiences were very different. Here’s a summary of our wine tasting stops and highlights of what we experienced:

Ferrari-Carano’s Seasons of the Vineyard Tasting Bar and Boutique

Summary: I’ll be honest with you. I never realized the name of this wine bar was so long until just now. But if I had, I might’ve seen the signs of what was to come…an unnecessarily long wait.

This was the first wine bar Mr. Wino and I visited and it was a disappointing first impression. I’ll set the scene: there was one other couple in the tasting room and two servers behind the wine bar. One of the servers was on the phone. We understand that sometimes it takes a moment for servers to switch gears when customers come in but we literally sat there for five minutes while the lady server stayed on the phone and the other server stayed with the couple. Neither acknowledged us during that time.

Confused, we were about to leave when the lady got off the phone and finally handed us a wine tasting list. $25 for five tastings! Yikes! For a second we thought we lost our way and were in Napa! As a wino…this was too much. But since we waited so long we decided to just go ahead and split the tasting (an old wino trick to saving money 😉 ) The wines were not cheap by the bottle either – ranging from around $35 to $90 per bottle.

The final blow that did us in…was the unnecessarily long time it took to get the next taste. The server was distracted and it was pretty clear we were not the priority.  Normally we list a summary of the wineries we visit, but honestly…this is not a place for winos. It was too stuffy, not approachable, and too expensive. It was simply not a wino’s style. We’ll leave this place for the wine connoisseurs of the world.


Winery Overview

Information current as of January 2018

Tasting Cost: $25 per person tasting fee for five tastes.

Hours: Open 7 days a week; 11 a.m. to 6 p.m.

In town/Rural/Remote: In-town, next to many other tasting rooms

Location: 113 Plaza St, Healdsburg, CA

Quality of Wines (1-5 smiley faces): 🙂 🙂 🙂

Winery Style: N/A – not a place for winos.

Space for Weddings & Events: No. Small boutique winery in town.

Website: https://www.ferrari-carano.com/tasting-rooms/seasons-vineyard-wine-shop/


Portalupi Wine

Summary: Our next stop redeemed Healdsburg for us. Portalupi Winery is a little closer to a wino’s style – friendly, reasonably affordable, fun and unique. It is located a couple blocks back from the plaza but is right next to several other wineries. Tastings were 3 wines for $10 or 6 wines for $20. Fees are waived with the purchase of a bottle (for 3 tastes) or 2 bottles (for 6 tastes).  Overall, we like to get five tastes for $10 or less but this was a little closer to our target.

Portalupi Winery is a Traveling Wino Favorite in Healdsburg.

There was a great selection of reds, which worked great for us as this is our favorite. Pinot Noir, Barbera, Petite Sirah and several Zinfandels were on the menu, with our favorite being the Zin and Barbera. Another added perk to our tasting experience is that they also offer a few “Bites”. Its a little on the pricey side but we split the $25 charcuterie plate and it was plenty for us both. For those winos out there that aren’t fancy (we aren’t!) charcuterie is a french word pronounced  “shahr-koo-tuh-ree” and its another word for a “meat platter” 🙂 No matter how you say it…it was delicious.

The atmosphere here was fun. The servers were very friendly and attentive. They were knowledgable about the wines and very approachable to ask any questions. There’s a seating areas with comfortable bright lavender couches up front and a couple of other areas towards the back of the room. There’s even some games to play while you are there. One other highlight that fits the wino style perfectly is their “milk jug” refillable wine jugs with wines on tap. They serve their “Rosso” red wine but its delicious and affordable. A jug costs $26 and refills are $22!

Overall, we had a fantastic time here at Portalupi. We will happily return here again on our next trip to Healdsburg.


Winery Overview

Information current as of January 2018

Tasting Cost: 3 wines for $10 or 6 wines for $20. Tasting fee waived with 1 bottle purchase (for 3 wine tasting) or two bottle purchase (for 6 wine tasting).

Hours: Open 7 days a week; 11 a.m. to 7 p.m.

In town/Rural/Remote: In-town, next to many other tasting rooms

Location: 107 North St, Healdsburg, CA

Quality of Wines (1-5 smiley faces): 🙂 🙂 🙂

Winery Style: Friendly & Fun

Space for Weddings & Events: Yes. A private event space, the Candela Room can accommodate smaller events or you can rent out the entire tasting room for as many as 32 sit down or 55 reception guests (no wedding ceremonies but great for wedding or other celebrations).

Website: https://www.portalupiwine.com/


Williamson Wines

Summary: Williamson Wines is also a wonderful place to visit in Healdsburg. Talk about “bang for your buck”! Williamson has come up with a fantastic concept to introduce wine lovers to the art of pairing food with wine. Honestly, when I first heard about pairing wine with food I thought, “What a load of crap! Just eat the food and enjoy it with your favorite wine.” I thought it was some goofy overblown thing to sound pretentious. But, Williamson was the first winery to show me exactly what pairing is about. And they did it in a way that was NOT pretentious. And guess what? It was absolutely free!

Williamson checks all our boxes: affordable, fun and unique!

Here’s how it works: For groups up to six guests or less…and first-come-first-serve on the seating (they only have ten tables), you can sit in the charming tasting room and taste five wines for free. A very knowledgeable server will have you taste the wine first alone and then bring you a tiny “everyday fridge food” item to taste with the wine. Generally this means mustard, jams and cheeses. You get to see how the wine changes flavor depending on what it is paired with…and you get to see how it can enhance the flavor or “take it down a notch” if the wine is especially strong. And the best part about this experience is that it is fun, educational and down-to-earth. You are not getting some obscure gourmet experience. You are getting a real-life, fridge-food experience that only a true wino can appreciate. It was enough for me as a skeptic to become a believer in food pairing.

For those folks who do want to explore the food pairing even more, they do also offer a few fancier, gourmet options too, so it is a great place to go for foodies and non-foodies alike. The wines are good and you can’t beat the price point. One thing to note about this place is that it is super popular especially on weekends (and we totally get why). In fact they note on their website that the tasting room “is usually packed Friday through Sunday. Guests, including famous, important, or influential people, may have to wait for a table, and may very well be standing next to some of the county’s business or political leaders, or other local celebrities.”

As winos, we appreciate the sarcasm in this comment, and we appreciate that the owners treat everyone the same, no matter how important they think they are. Williamson Wines definitely gets high marks for being non-pretentious in our book!! This is a Wino’s pick for us!


Winery Overview

Information current as of January 2018

Tasting Cost: Free for the “Fridge Foods and Fine Wines” tasting!!! Other “fancier” food and wine tasting pairings are $50 and up.

Hours: Open 7 days a week; 11 a.m. to 7 p.m.

In town/Rural/Remote: In-town, next to many other tasting rooms

Location: 18 Matheson Street, Healdsburg, CA

Quality of Wines (1-5 smiley faces): 🙂 🙂 🙂

Winery Style: Educational, Fun & Friendly, Unique

Space for Weddings & Events: Yes. Several private event spaces can accommodate smaller events or meetings for as many as 8 to 100 guests (no wedding ceremonies but great for events, wedding dinners, or other group celebrations).

Website: https://williamsonwines.com/


Gustafson Family Vineyards

Summary: Next stop on our Healdsburg wine tasting venture was the final winery of the day – Gustafson Family Vineyards. Don’t let the elegant exterior and classy interior fool you into thinking its stuffy. Because it is absolutely NOT stuffy. The servers are friendly, welcoming and the atmosphere is fun. One of the best aspects of this tasting room is the great choice on your tastings. You can taste four wines for $10 (pretty close to the wino’s target…) or eight wines for $20.

Healdsburg’s Gustafson Winery is both classy and fun…a rare combination we love.

The other great thing about this place is their wines are very good, especially their reds. It was refreshing to see such high quality wine for a fairly affordable tasting fee. The cost of bottles was very good too. They ranged from $20 per bottle to a maximum of $38 per bottle for the Cabernet. We thought their red blend was fantastic and it sat at the lower end of the scale at $24 per bottle. And their tasting fee is refunded with the purchase of a bottle, which is another nice little perk.

One other thing to note is that Gustafson has another tasting room at their vineyard in a rural setting if you like the more scenic experience. And they work with the restaurant across the street and several “wine and food” tours to offer wine pairing experiences too. These are at additional prices but it is a great option for he “foodies” out there. Overall, we would say that the highlight of wine tasting at Gustafson Family Vineyards was that we got a high quality experience at a reasonable price in a very friendly atmosphere. We would definitely return here again in future visits to Healdsburg.


Winery Overview

Information current as of January 2018

Tasting Cost: Taste 4 wines for $10 or 8 wines for $20. Fee refunded with the purchase of a bottle.

Hours: Open Thursdays through Mondays from 11 a.m. to 6 p.m.

In town/Rural/Remote: In-town, next to many other tasting rooms

Location: 34 North St. Healdsburg, CA

Quality of Wines (1-5 smiley faces): 🙂 🙂 🙂 🙂

Winery Style: Elegant, Fun & Friendly

Space for Weddings & Events: No, not at tasting room. However, they do have a vineyard location that might accommodate special events.

Website: https://www.gfvineyard.com/