healdsburg
If Sonoma is Napa’s more approachable younger sister, then Healdsburg is the cooler, quieter cousin with a thing for good wine and even better design. Healdsburg is a lesser known, magical part of California wine country that cannot be missed. It has a variety of places to stay, what I think are the best restaurants in California wine country, and stunning wineries and tasting rooms that you can (almost) always find space at.
Where to stay
H2, Harmon Guest House, and Hotel Healdsburg are three of the hotels in downtown Healdsburg. They are all owned by the same company, have slightly different vibes, and are all equally enjoyable. Hotel Healdsburg is a bit older and more romantic (my fiance and i took our first trip as a couple there!) while H2 and Harmon guest house feel a bit more urban with mid century modern influences. All are great, affordable (!) options. While you can’t expect resort amenities or vineyard views - these hotels are downtown after all - all three hotels have a swimming pool for guests to enjoy on warm days.
For those looking to splurge - or if you’re staying downtown and in need of a spa day - the Montage is your luxury option in this part of town. Montage properties are known for luxury, service, and feeling deeply tied to their surroundings and the Montage Healdsburg is no exception. Just 10 minutes North of downtown it is easy to get to and is located on a vineyard so it truly has the feel of a wine country getaway. It’s vineyard views, restaurants, and spa are a delightful escape from downtown.
One of the newer additions to Healdsburg is the Madrona. A converted private Victorian estate, the Madrona is quite different than anything else you’ll find in wine country. It has a pool, a vibrant restaurant, and a bar with excellent cocktails and little nooks to cozy up in.
You truly can’t go wrong with any of these options.
Where to eat
Healdsburg has some of the greatest restaurants in wine country - or dare i say the bay area. Here are rapid fire reviews:
Valette ($$–$$$) – Elevated wine country cuisine with a local soul and a touch of swagger.
SingleThread ($$$$) – A Michelin three-star stunner blending Japanese precision with Sonoma bounty.
Sushi by Scratch ($$$$) – A moody, secretive omakase that feels like a speakeasy for sushi lovers.
Barndiva ($$$) – Farm-to-table magic served in a fairy-lit garden straight out of a dream.
The Matheson ($$–$$$) – A stylish three-story spot where the wine wall and rooftop views steal the show.
Quail & Condor ($) – A cult-favorite bakery turning out next-level pastries and breads with heart.
Lo & Behold ($$) – Retro charm and bold cocktails meet playful plates in a buzzy neighborhood hangout.
Little Saint ($$–$$$) – A serene, plant-forward haven where art, music, and vegetables share the spotlight.
tip!
eat at ROOF 106 at the matheson for a fun, casual option. think: outdoor lounge seating, pizzas, and cocktails, perfect after a day of wine tasting.
Wineries
And when it comes down to it, the wine is what you ultimately came for. There is no shortage of incredible wineries in Healdsburg but highlighting a few of my favorites here:
Flowers – A coastal-chic dream of a winery where modern architecture meets wild Sonoma elegance (and yes, the garden is as dreamy as the Pinot).
Aperture – Bold reds, gallery-level design, and serious “cool art collector who also makes wine” energy.
Twomey – A low-key gem from the Silver Oak family pouring smooth Pinots and Sauvignon Blancs with vineyard views for days.
MacRostie – Warm hospitality, sweeping valley views, and a tasting room that feels like the pages of a West Coast interiors magazine.
Jordan – Old-world glamour with a Sonoma twist—think French château vibes, estate tours, and wine-paired bites on the terrace.
Medlock Ames – Under-the-radar charm with organic vineyards and a rustic-modern vibe; great for chill tastings and vineyard walks.
Bacchus Landing – A collective of boutique tasting rooms in one gorgeous courtyard setting—great if you're with a group or want a choose-your-own-adventure moment.
