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Near the more popular Sonoma and Napa, Healdsburg is quaint and primed for a slower pace.
Healdsburg, California, was a small farming community, filled with apple orchards, which later turned into vineyards. Hearing from a server at one of the restaurants who grew up in the area, in school you were either the child of a farmer or orchard owner. However, this little town has become very refined, but sticks to its roots. There’s a strong Spanish flair woven into this bougie community.
Travelers come to Healdsburg for great wine, upscale shopping, and delicious dining, but most importantly, to heal the soul in a tech and productivity driven world.
Getting To Wine Country
Fly into Santa Rosa’s Charles M. Schulz Airport, which is filled with happy Snoopy vibes. Charles Schultz retired to the Santa Rosa County area and the airport is filled with Peanuts drawings and characters. From here, you’ll be a short 15-minute uber ride to the Healdsburg town square (versus a 2+ hour drive from the San Francisco airport.)
Cozy and Quaint
The Cottages, specifically the Clementine cottage, is perfectly situated just blocks away from the town square and everything that you will walk to (seriously, a 5-8 minute walk anywhere.)
Modern, cozy and perfectly appointed, the luxurious layout and design of the Clementine cottage is ideal. Amenities include an overstuffed king size bed, walk-in shower with oversized towels, an electric fireplace in the living area, tiny kitchenette with refrigerator and microwave for leftovers. The back patio leads out to a private space and is just steps away from an outdoor pool.
Buy a local bottle of wine and take your wine glasses out on the front porch or back deck for one of the most relaxing experiences.
Delectable Dining
Staying at The Cottages, consider this your neighborhood café, literally half a block away. Heavenly named, this wine (bottle) shop, bakery, bar, and restaurant, is mixed with the feel of a book shop with couches and cute nooks and crannies with the hippest cafe. It’s really got everything you need for a relaxing visit: cuddle up on a couch with a book and a coffee (or wine, depending on the time of day) and enjoy a slice of quiche, avocado toast or just nibble on a delicious peanut butter/chocolate cookie.
With 87 wines on tap, a delicious menu and the coolest evening vibe, we loved our time here. Everything plays into the scene here: lighting, artwork, spacing and design of the interior. The sommelier does a fantastic job of walking you through local wine choices, especially the hearty pinot noir list. His recommendation was to decant the red, “to let it out and play for a while as it’s been cooped up for sometime.” We paired this with a unique burrata, savory risotto and grilled fish.
This French bakery is the place to be, for tourists and locals alike. Along with a beautiful bakery display (they even have dog biscuits with samples for the Fido taking), they also have a cooler fit for the perfect picnic. Choose a sandwich and even ask for it to be grilled; pair that with a salad and a bottle of wine. They also have a “we make it, you take it” cooler where you can grab the perfect ingredients to make your own pizza at home.
Try the hearty Chilaquiles (remember how I mentioned the Spanish influence earlier) or the Croissant Breakfast sandwich (on a butter croissant with egg, bacon, avocado, cheddar cheese, house aïoli), and a side of seasonal fresh fruit.
Pair one of those with a cappuccino or latte, or go ahead and order something like a rosé or midday cocktail with your brunch.
Right on the town square, this Italian bistro has it all: a sidewalk cafe, outstanding Italian dishes and “liquid appetizers” (a la craft beer and local wines). We highly recommend starting with the truffle fries (which you can also find in Italy), then move on to the Beef Bolognese, followed by the Napoliana Margherita pizza.
At a cute vintage house, with an outstanding backyard courtyard, teeming-with-hip bar, this Spanish tapas restaurant es bueno. As per the server’s instructions, they recommend you order 3 to 4 tapas for two people. We highly recommend those include the: Pan Tomate, the Creamy Chicken Croquetas, and Crispy Skin Chicken Thighs with green olive tapenade and aleppo vinaigrette. Pair those delights with a Laughing Monk Pilsner from San Francisco.
Situated just a few blocks from The Cottages, this authentic Italian restaurant’s motto is “Come as Friends, Leave as Family.” With a fantastic back patio, this menu is a standout! We had read about their famous Black Cod with cauliflower puree online. However, because we are fanatics for housemade pasta, our favorite dishes were the Raviolo al’ Uovo with Summer Truffle and Sage Brown Butter and Basil Pesto Pizza. The ambiance in combination with the dishes and impeccable service makes this one a meal to remember.
Goodnight’s Prime Steak + Spirits
Hailing from Texas roots, and opening on the town square in August 2023, this steakhouse exudes excellence! With Chef David at the helm, a stunning interior, impeccable service and stellar menu, this is a treat! Head straight to the mouth-watering steaks, perfectly seared in their unique style (pick any, you can’t go wrong). You’ll order one sauce and one salt (truffle, yes please) for your steak that you can drizzle, dip or coat in any way you decide.
Choose sides where the carbs and calories don’t count for this experience. Go for the Yukon Gold Potato Purée (melts in your mouth). Upon the writing of this, the creamy mac’n’cheese and broccolini were no longer showing on the online menu, but every dish we tasted was above par. Pair this standout meal with a bold cabernet and don’t forget the dessert!
For Chilling and Healing
Touting 30+ zinfandels, winemaker Diane Wilson has been smashing grapes into perfect juice for 30 years. Impressing the most picky Texan oenophile, she’s won five Houston Rodeo medals & even a grand champion saddle. The setting is peaceful, made even better by the winery’s own 13 year old Wakanda (all great wineries have dogs). Bring a picnic out to enjoy under the shade trees with a tasting or bottle.
Tucked back in a beautiful hidden corner, and just off the town square, the Spa is ready to melt your computer-driven stress away. Book a 50-minute deep tissue massage and follow that up with a soak in the covered Jacuzzi and heated outdoor pool. This setting is perfect to spend an entire day so don’t rush. I forgot my sunscreen and they even gave me little samples of sunscreen to use out by the pool.
So when you’re ready for a little mind/body/spirit healing, head west to Healdsburg for wining, dining and whiling away a minimum of three nights. All you need is some comfortable walking shoes, a good book and some intentional permission to rest.
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Cover Photo Ally Brayton
Marika Flatt, Outstanding Austin Communicator 2021, is the Travel Editor of Texas Lifestyle Magazine. She began her travel writing career in 2002, and can be seen as a contributor on TV shows across Texas, such as KVUE, Daytime (FOX), San Antonio Living, Good Morning Texas, and KXAN! Marika spent five years as the voice of the “Weekend Trip Tip” on NPR’s Texas Standard pre-Covid. She adores a cool patio evening with a glass of cabernet and a cozy fire indoors.
