Make Yourself at Home in Healdsburg


No longer the smaller, more quaint cousin to booming Napa and Sonoma, Healdsburg now boasts posh accommodations and world-class cuisine while retaining its quintessential country vibe. Dozens of vineyards are a stone’s throw away in nearby Dry Creek, Alexander, and Russian River Valleys; however, Healdsburg’s allure entices you to stay within its limits and there’s no reason to stray too far.

Visitors tend to frequent the chic H2 and the classic Hotel Healdsburg. But, the city claims an abundance of offbeat lodging mere steps away from the main square. 


Once a set of artist’s studios with squatters occupying the metal and wood buildings, Peter and Pat Lenz built Duchamp in 2000. The collection of artist-designed cottages are flanked by gorgeous olive trees imported from the Central Valley. The property maintains a minimalist ambience with calming neutral colors, stainless steel baths, and black tile. Comfortable rooms are outfitted with huge showers and fireplaces, European breakfast is served, and a pile of lifestyle magazines will keep you occupied as you laze by the heated pool with the trickle of Foss Creek nearby. Duchamp was influenced by sculpture made by renowned French artist Marcel Duchamp, and the art of proprietor Pat Lenz is scattered throughout (note the life-size pink poodle in the lobby). The Lenz’s also operate the Duchamp winery (a former slaughterhouse with 30-foot ceilings!) which specializes in Syrah. 

A peek inside Modern Cottages

If you’re crazy for design, book a stay at Modern Cottages, where the four mid-century-inspired cottages are named after prominent designers Ray and Charles Eames, Eileen Gray, and George Nelson. The cottages are graced with sleek American black walnut floors, fireplaces, and beds are wrapped in luxurious Matteo linens handmade in LA. A stay in Eileen entitles you to a patio view of two towering redwoods. There’s a jacuzzi and serene pool, and guests can enjoy a complimentary coffee and pastry from SHED a few steps down the block. Located on the opposite side of Foss Creek, Modern Cottages was the original iteration of neighboring Duchamp, but is now separately owned and operated. 

If you really want a home to call your own, book the Moorish-inspired Cypress House for you and your guests. Unassuming and tucked away on an alley off of the main street, the grandiose two-bedroom, two-bathroom apartment has ample space to stretch out and get very comfortable. A rooftop terrace flaunts downtown views, gorgeous tiles line every room, and the capricious kitchen has state-of-the-art appliances and a huge dining table ideal for a big, loud dinner with your favorite people. Sink into the plush threads of the king bed beneath the beamed ceiling and soak the day away in its luxurious tub (yes, it’s possible to feel like royalty). There’s also high-speed internet, gated parking, and the town square is a super short stroll away. A studio apartment is also available to rent.

A former motor shop turned mixed-use building smack dab in the center of town is the unassuming home of three 3-bed, 3-bath commodious apartments. Ranging from 1,300 – 1,700 square feet, Two Thirty-Five luxury suites were opened in 2012 by the convivial Cuban-American Diaz family and are a cool fusion of vacation rental and hotel (the family is more than happy to play concierge and offer up advice and direction). The sleekly decorated accommodation is ideal for families and large groups. Three couples or a troop of bridesmaids or groomsmen would feel perfectly at home here. A legit kitchen is large enough to host a private chef, a group tasting, or a balls-to-the-wall breakfast where everyone participates. Each of the suites showcases art from local artists (Brad Brenner is one), and amenities include multiple shower heads in the bath, state-of-the-art Nest thermostats, custom made furniture, California king beds, and free parking. The delectable Portuguese Café Lucia is just downstairs.

Plenty of space to stretch out at Two Thirty-Five

 The Grape Leaf Inn is in the midst of a total overhaul by its new owners who also own eight wine properties nearby. The 1901 Victorian is trading in its frilly darkness for a modern, bright, and luxe theme. More of a boutique inn versus a B&B, the 11 existing rooms have spectacular angles, fireplaces, plush beds, and skylights, but try to book one of the two spacious suites, slated to be complete later this fall, which will be flanked by private patios and outdoor showers. Breakfast will be served at a huge custom farmhouse table, and French doors allow access to the wide wrap-around porch. Guests can also laze by the brand new plunge pool or dip in the hot tub, and a massage room is also in the plans. There is even a speakeasy hidden in the basement behind a moveable bookshelf! The property has not had a revamp since the ‘80s, and the transformation thus far is magnificent. 


Why drive to the vineyards when you can sip and stroll home? Just off the square, Cartograph eschews traditional Chardonnay in favor of an excellent dry Riesling that the proprietors pour from a five-gallon keg. The self-proclaimed “nerdy” winery facilitates a social experience with a smart s-curve tasting counter that allows conversation without needing to lean over your counterparts.The tasting room is minimalist and cool in style; their logo (also displayed on the wall) is a neat interpretation of the two owner’s paths to Healdsburg.

Interior of Cartograph

 Across the street, Banshee radiates the laid back vibe of a homey Sonoma living room with various nooks where you and your group can gather to sample the goods. The warm setting flaunts reclaimed wood doors and walls, beautifully distressed leather furniture, and an antique communal table. The ambiance is amplified by spinning vinyl in the background and they also showcase a collection of vintage knick-knacks for sale. Wine highlights include the Mordecai blend (yes, it’s a Royal Tenenbaum’s reference) of Sauvignon Blanc, Chardonnay, and Viognier, though the tasting room’s best foot forward may be it’s Sonoma County Pinot Noir in which nine vineyards are represented. Lest I not forget to mention the cute boys who work there. Next weekend, the tasting room hosts the eclectic music festival Banshee Fest and there are still some tickets available. 

Sit back, relax, and imbibe at Banshee


Post up at the pole position for people-watching at Pizzando and prepare your belly for an afternoon of wine tasting by indulging in their thin crust, wood oven pizzas, homemade pastas, and creative appetizers. A simple mushroom pizza with creme fraiche, dried herbs, and chile hits the spot and, for the love of God, try the burrata. 

Shed has received plenty of press for its ginormous farmhouse lulu of steel and glass that houses everything from a café to locally sourced goods to workshops for sustainable living. It’s a must stop.

Pork belly biscuits and Dungeness crab tater tots at Chalkboard. Photo courtesy of Thanh T./Foursquare

 Save the splurge for an evening at Chalkboard where all your dreams of a locally sourced farm-to-table meal will come true. The menu is inventive and packed with flavor (the restaurant gets many of its ingredients from a three-acre organic garden in Sonoma). Chef Shane McAnelly is especially proud of his crudos and homemade pastas, don’t miss them, and even the desserts, courtesy of pastry chef William Woodward, are out of this world. Highlights include scrumptious pork belly biscuits, king trumpet mushrooms, and the orgasmic Tcho chocolate bread pudding. Outdoor dining has been an option since June when a little-used pool belonging to the adjacent Hotel Les Mars was filled in. The hotel library next door is also worth a look.  

And a visit to Healdsburg is not complete without a visit to Barn Diva where you can dine al fresco in a lovely, spacious garden or feast inside and marvel at the beautiful interior. The menu rotates seasonally and a recent visit yielded delicate yellowfintuna sashimi, saffron aioli, avocado, ponzu, and pickled fresno chili followed by a signature heirloom tomato BLT with crisp bacon, avocado, butter lettuce, aioli, basil, and crunchy fries. The wine and cocktail list are sure to tempt, but equally as satisfying are their booze-free options like the Lift, a refreshing taste of watermelon juice, lemon verbena, and lime. Next door, poke around at Studio Barndiva which showcases a wide-ranging selection of art (it’s also where guests pick up the keys for Modern Cottages).  


Healdsburg is just over an hour drive from San Francisco. Flights from San Diego, Los Angeles, and even Denver fly into the Charles M. Schulz Sonoma County airport in Santa Rosa.