TRAVEL WINE COUNTRY || Why Healdsburg Should Be at The Top of Your List

I remember when I first moved to San Francisco, I was beyond excited to have such close proximity to wine country. 45 minutes to 1 hour away?? Can you say day trip? However, where to start? There are soooo many incredible wineries, tastings and dining options that it can quickly become overwhelming.

A haven amongst the chaos and the cutest town that should move to the top of your list is Healdsburg. It’s a charming wine-lovers paradise nestled between Dry Creek Valley, Alexander Valley and Russian River Valley. All three are AVAs, American Viticultural Areas, so most of the downtown Healdsburg wine tasting rooms source their grapes from these areas and may also have their flagship vineyard tasting room in this area, too.

And the best part?? Everything is walking distance. From your hotel to the hot new restaurant in town to your next wine tasting, you can walk! Quickly making this destination ideal for a romantic weekend getaway or bachelorette soiree or birthday celebration.

So when should you book your trip here? Honestly, it’s perfect year round; however, the winter is one of my favorite times to go. There’s just something about bundling up and sipping on a bold red during the colder months. I recently went in December over the holidays and it had this magical “did I just walk into a Hallmark holiday movie?” vibe with carolers and friendly shop owners on every corner. HUGE THANK YOU to Stay Healdsburg for hosting us and playing tour guide!

Other events to plan your trip around:

Tastemaker Weekend

This first annual weekend occurs in January and is an opportunity to meet and learn from the Tastemakers of Healdsburg. They offer so many exclusive hands-on experiences from an authentic Italian wine cave dinner to a pastry making class at a popular local bakery to a floral design class at an organic flower farm. And of course these all pair well with wine!

A special benefit of attending this weekend is 50% off your second hotel night if you do one of the experiences. Check out all participating hotels here. And a portion of each Tastemaker Weekend ticket sale goes to support the Healdsburg High School’s culinary program!

Healdsburg Jazz Festival

This annual festival has a 22 year history and is generally scheduled in the beginning of June. Grab your glass and check out all the jazz filling the air.

Harvest Season

Not an actual event, but definitely a time to be in wine country for the special harvest parties and events. Check out what is going on during late August through early November! Depending on the winery, you can watch grapes get crushed and admire the hustle of winemakers as they process their hard work.

Wine Road Events

These events take place quarterly and feature wineries all over wine country including Healdsburg. Great for getting a deal if you plan to wine taste all weekend and hop from location to location. There’s even a barrel tasting event where winemakers share their work in progress and you can taste straight from the barrels! This unique experience generally takes place in March.

If you can’t make it during one of these events, don’t fret. Use their guides as inspiration and plan your own jam-packed (pun intended) weekend. I’ve listed a few of my favorite stops below as further inspiration.



  • Davero Farms & Vineyard: looking for more than a tasting room? Take the journey (1 mile away from the city center) here and walk through the vines. This vineyard is all about teaching visitors their biodynamic farming ways and spoiling them with yummy Italian varietals (aka wines for those thinking what the heck is a varietal).
  • Banshee: calling all hipsters! This spot not only offers wine but also a cool atmosphere filled with records to play and nooks made for instagram.
  • Coursey Graves: a newer tasting room in the area with a modern flair and something for everyone from Chardonnay, Pinot, Cab to Syrah.
  • Soda Rock Winery: their new location is now open and a great chance to support the winery that burned down in the Kincade Fire. A huge misunderstanding is that wine country is on fire and not a place to visit, which couldn’t be further from the truth!! And it’s so important to support the area now more than ever.
  • Grapeseed Wine: want wine and art? Look no further. Sip favorites amongst inspirational paintings and sculptures at the Paul Mahder Gallery.
  • Cartograph Wines: this winemaking couple is so cute and passionate with a true love of science. Known for their pinots, so this was naturally a favorite of mine!


  • Oakville Grocery: pop in for a quick bite and selection of fresh options. Don’t let the name grocery fool you, this place serves up gourmet options!
  • Single Thread Farms: a dining experience of a lifetime. This 11-course tasting menu combines the brilliance of a farming wife and chef husband.
  • Chalkboard: a casual and contemporary option combining all the flavors of Sonoma. Try the chocolate pasta, yup you heard me correctly, CHOCOLATE PASTA.
  • Costeaux Bakery: perfect for breakfast or a mid-day treat. This bakery has been a Healdsburg staple since 1923.



My girl Kara from Whimsy Soul who I had a chance to travel with on my last trip to Healdsburg put together this super helpful map with top restaurants, wineries and shops. As you can see everything is sooo walkable, it’s incredible!


I hope you enjoy all Healdsburg has to offer!! Comment or send me a note at if you have more recommendations to add!!