The Perfect Weekend Getaway to Healdsburg, California
This charming small town in Sonoma is my favorite place for a wine country getaway.
Having lived in San Francisco for over 11 years, I’ve spent plenty of time exploring nearby wine regions like Sonoma and Napa. While I’ll never turn down a weekend in either, my go-to spot for a wine country getaway lately has been Healdsburg—a charming small town at the northern end of Sonoma. It’s a bit more of a drive than other parts of Sonoma, but at under two hours from most of the Bay Area, it’s well worth the trip.
In the past few years, I’ve watched Healdsburg evolve with incredible new hotels, restaurants, and wineries, while still holding onto its small-town charm. With a mix of newcomers and long-standing favorites, it’s easily my favorite wine country escape. Use this travel guide to plan your trip to Healdsburg.
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Healdsburg Hotels: Where to Stay
Harmon House
Harmon House
There are so many amazing hotels in Healdsburg to choose from—from ultra luxe resorts to charming boutique hotels. These are my go-to recommendations:
Harmon House + H2
📍 Central Healdsburg
Find a room at Harmon House: booking.com // expedia // hotels.com // website
Find a room at H2: booking.com // expedia // hotels.com // website
Harmon House and H2 are sister properties side by side right off Healdsburg’s main square. For walkability and convenience, it’s hard to find a better location. I usually stay on the Harmon House side but both properties are very similar in design, comfort, and price. Each hotel has their own pool and guests are allowed to use both. Rooms are spacious, beautifully designed, and some even have balconies. There’s also a rooftop bar at Harmon House, perfect for happy hours.
The Madrona
📍 A 3-minute drive from downtown Healdsburg
Find a room: booking.com // expedia // hotels.com // website
I am obsessed with this maximalist, historic mansion-turned-boutique-hotel. Originally built in 1881, The Madrona reopened in 2022 after an extensive renovation that transformed it into a design-forward retreat while preserving its soul.
Expect eclectic interiors, a lush garden, a stunning pool, and a breezy patio bar and restaurant where both locals and guests gather. Accommodations range from cozy mansion rooms to private bungalows tucked into the gardens.
Montage Healdsburg
📍 5-minute drive from downtown Healdsburg
Find a room: booking.com // expedia // hotels.com // website
Set on 258 acres of vineyards and oak trees, Montage is the most luxurious resort and spa in Healdsburg (at least for now 😉—Appellation will be opening in 2025). The property blends seamlessly into the landscape with treehouse-style rooms, all featuring large outdoor decks. The on-site restaurant, Hazel Hill, is an incredible spot for sunset dining with sweeping valley views, while guests will enjoy their spacious pool area during the day. While you could spend your entire stay at Montage, it’s a quick drive (or a hotel-arranged e-bike ride) into town.
💡 Advisor rate available—contact me for perks like resort credits and room upgrades.
Hotel Les Mars
📍 Central Healdsburg
Find a room: booking.com // expedia // hotels.com // website
Hotel Les Mars may not be the trendiest spot in town, but it’s one of the most classic and elegant. This small, 16-room Relais & Châteaux property is just two blocks from the plaza and across from the Saturday Farmers’ Market. Expect plush beds, marble-lined bathrooms, and wood-paneled libraries—a great pick for travelers who want a luxurious yet intimate experience in the heart of wine country. Not going to lie, I was a bit hesitant based on the photos but the place is much nicer IRL and I ended up really enjoying my stay here.
Hotel Trio by Marriott
📍 15-minute walk from downtown Healdsburg
Find a room: booking.com // expedia // hotels.com // website
Hotel Trio wouldn’t be my first choice but let’s be real: hotels in Healdsburg can get pricey—especially on weekends and peak travel season. In that case, this is my go-to for a more affordable option. It’s reliable, clean, quiet, has a pool, and the location’s not bad. It’s about a 15 minute walk to the plaza (take the bike path) but there’s also a shuttle and loaner bikes if you prefer.
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Where to eat in Healdsburg
Quail + Condor
Healdsburg has seen quite the evolution of its food scene over the past decade or so. From Michelin-starred Singlethread opening its doors in 2016 to a small boom of new eateries in the COVID and post-COVID years, it has slowly become one of the best foodie destinations in Northern California. I will surely miss a spot (or five) but here are some of my favorite places to eat in Healdsburg.
Brunch, Breakfast, and Coffee
Black Oak Coffee – Many hotels in the area serve breakfast but if yours doesn’t (and maybe even if they do), grab a coffee and avocado toast from Black Oak. It’s a community-minded café that also donates 10% of house espresso sales to charity. Flying Goat Coffee is another good caffeine stop.
Quail & Condor – This adorable bakery on the edge of town is from a group of SingleThread alums, known for their croissants, sourdough bread, and pastries like black sesame calamansi cake and Parmesan onion biscuits.
Parish — For a heartier brunch, head to New Orleans style restaurant, Parish. I’ve yet to go but hear great things.
Lunch
Roof 106 at The Matheson – Dustin Valette opened the doors of The Matheson in what used to be Snowflake Bakery, his great-grandfather’s bakery. On the bottom floor, there’s a lively bar, wine wall, and upscale tasting menu style restaurant. But come lunch, you’ll want to head to the roof (Roof 106) for wood-fire pizzas and creative apps like the togarashi puffs.
Dry Creek General Store – If you’re out and about wine tasting or biking in Dry Creek, this is the spot to stop. It’s long been a favorite among visitors and locals alike for hearty, made-to-order sandwiches.
Little Saint – I love Little Saint for lunch or dinner. This colorful space was originally launched by the team from SingleThread as a fully vegan restaurant, showcasing fresh, seasonal produce and creative meat-free dishes even non-vegans will love. It’s no longer associated with SingleThread but the food is still as tasty as ever. Plus: they have great cocktails and mocktails, and regularly host musicians for live music in their upstairs space.
Troubadour – Like Little Saint, this spot works for lunch or dinner—but you’ll get two very different experiences. In the day it’s a delightful, French-inspired sandwich shop. By night, it transforms into an intimate 20-seat French bistro. The menu is seasonal, featuring dishes like mussels with onion and chervil.
Dinner
The Madrona – Even if you don’t stay at The Madrona, it’s worth swinging by for dinner or cocktails. If it’s early, grab a martini and plate of oysters and lounge on the porch (which, seriously, brought me back to my southern porch-sittin’ days in Virginia). Otherwise, stay for dinner at their indoor/outdoor restaurant that serves fresh, Californian food in a vibrant atmosphere.
SingleThread – It’s impossible to talk about food in Healdsburg without mentioning SingleThread, the three-Michelin-starred restaurant that has gotten much acclaim since opening in 2016. It serves beautiful, Japanese-inspired dishes made using ingredients from their nearby farm. This is the kind of place you travel for and reservations are most definitely required (far in advance). Still, if it’s a special occasion and you’re willing to splurge, it’s such a wonderful treat.
Bravas Tapas – For a more casual but still delightful dinner, head to Bravas Tapas, a local favorite for Spanish small plates and fun vibes. Expect classics like patatas bravas and jamón ibérico alongside excellent gin and tonics.
Goodnight’s Prime Steak + Spirits — If it’s a hearty ribeye or burger you’re after, there’s no better spot than Goodnight’s. It’s simultaneously unfussy and stylish in a modern, welcoming space right on the square.
Lo & Behold – Another favorite is the laid-back bar and restaurant, Lo & Behold, which was recommended to us by a local bartender. The cocktails and fried chicken are favorites among regulars, but there’s a full menu of globally-inspired, creative dishes. Coconut shrimp toast and curry deviled eggs, anyone?
Happy Hour
Hazel Hill – The Montage’s restaurant, Hazel Hill, is located about a mile north of town in a beautiful, nature-filled location. Yes, you can stay for dinner, but at the very least grab a cocktail or glass of wine and enjoy the sweeping sunset views overlooking the rolling vineyards. They also have live music on some evenings.
Duke’s Spirited Cocktails — This lively bar on the main plaza was a COVID discovery for me, and maybe they hold a special place in my heart because they let me use the bathroom when I ordered a to-go cocktail. But I stand by it: the cocktails are good and the staff is nice. It’s worth a stop.
The Rooftop at Harmon House — Hazel Hill may have the better views, but The Rooftop is right in town and still a very fun place for happy hour overlooking Healdsburg’s main plaza.
I’ve yet to go but Society and Maison Wine Bar are two other great watering holes I’ve been recommended.
Dessert
Noble Folk Ice Cream – If you have any room at all, end your day with a scoop or two from local LGBTQ+-owned ice cream shop, Noble. The flavors are creative and ice cream well-made.
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Wineries + Tasting Rooms
Marine Layer in downtown Healdsburg.
This being Sonoma, there’s no shortage of amazing places to drink wine. Here are some of my favorites:
In-town tasting rooms
BloodRoot Wines is a casual, unfussy tasting room with high-quality, small-production wines at great prices. Very hip and I love that there’s a small outdoor space as well—great for nice days or visiting with a pup.
Marine Layer Wines – This winery focuses on coastal pinot noirs and chardonnays and yes they are delicious, but half the reason I come here is to enjoy the beautiful space, designed by Hommeboys. They also have snacks from Little Saint.
Banshee Wines – Think cozy lounge meets tasting room. Banshee makes great Sonoma Coast pinot noirs as well, but has been around for a bit longer.
Outside of the Plaza
Aperture Cellars (5 minutes from town) – If you love Cabernet Sauvignon, you’ll want to check out Aperture. Founded by a Napa-trained winemaker, this is one of the best places for bold, Bordeaux-style wines in Sonoma. I also love that they have great spaces for indoor and outdoor tastings.
Flowers Winery (10 minutes from town) – Like many wineries in this part, Flowers is known for their coastal pinot noirs and chardonnays. But I love the tasting experience because it’s well set up for any time of year: a big, spacious patio for nice days and a cozy tasting room with a fireplace for cold ones. Plus the snacks and food pairings are very tasty.
Bricoleur Vineyards (15 minutes from town) – Bricoleur is one of my favorite wineries, period. It’s a beautiful space with vineyards and a fully functioning farm with produce, bees, and all. Fittingly, their tastings revolve around food (seriously: there is no option for a tasting without unless you’re a member). Their picnic option is one of their most popular options. Grab a radio flyer, bottle of wine, lunch, and go make a picnic—dogs and kiddos in tow—anywhere you want.
Preston Farm & Winery (15 minutes from town, Dry Creek Valley) – Not going to lie, there are better wines in the area, but I love visiting this spot nonetheless. It’s perfect if you want a more relaxed wine tasting (or drinking) experience. Grab a bottle, a loaf of their fresh sourdough, and make a picnic on their lawn. Dogs and kids welcome and it’s a fun one to bike to.
Bella Vineyards & Wine Caves (15 minutes from town, Dry Creek Valley) – Bella is known for their bold Zinfandels and cave tastings. They also have some fun and creative tours, like a tour up the steep vineyards in their Pinzgauer truck, or a wine tasting slash hike combo, for something a little bit different. Their events are worth checking out too.
Note: one perk of staying in Healdsburg is that it’s easy to get to the Calistoga end of Napa too. This is probably the only place where I’d say it’s doable to taste in both Napa (Calistoga) and Sonoma (Healdsburg) in one day.
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Things to do in + near Healdsburg
Visit the Healdsburg Farmers’ Market
If you’re in town on a Saturday or Tuesday morning, don’t miss the Healdsburg Farmers’ Market next to Foss Creek Parkway. Wine isn’t the only thing being grown in this area, and the Farmer’s Market is a great showcase of all the amazing local produce and food. If you miss the farmers’ market, stop by local farm stands like Preston Farm and Winery (open daily) and SingleThread Farm at Dry Creek (open Thursday–Monday).
Go kayaking
Healdsburg is right near the Russian River and, especially on hot days, kayaking is a great activity to break up all the eating and wine tasting. For this, I’d recommend booking a tour with Getaway Adventures who handle all of the logistics—including lunch in a lovely redwood grove.
Bike the backroads
If you prefer two wheels, there’s also a lot of great cycling in the area. Getaway Adventures does bike tours and rentals in addition to their kayak adventures (they even have a pedal-paddle tour that combines both), but there’s also Russian River Adventures who runs an informative e-bike tour through wine country—complete with fully mic’d helmets so you can actually hear what your tour guide has to say.
Swim in the Russian River or lounge by a pool
When the temperatures rise, cool off with a swim in the Russian River. I like Healdsburg Veterans Memorial Beach (which is close by) and Steelhead Beach (a bit more of a drive towards Guerneville) for a BYOB day of floating and swimming.
Prefer a pool? Francis Ford Coppola Winery has a public pool adjacent to its tasting room. Reservations are required for a cabine ($220 for 4 people), but book out fast. Before COVID, they used to allow a limited number of people to show up day of and just throw a towel down on the lawn, but that’s no longer allowed.
Or, be strategic and make sure you book a hotel with a pool—which all of my hotel recs do. Coming for the day? ResortPass is another great alternative. You can use it to find day passes to hotels and resorts in the area.
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When’s the Best Time of Year to Visit Healdsburg?
Summer is the most popular time of the year to visit Healdsburg and Sonoma county overall. I love visiting this time of year, especially if I’m feeling tired of the cold weather in San Francisco, but word to the wise: it can get hot, like over 100 degrees hot, which isn’t for everyone.
Overall, I think spring and fall are the best times of year to visit. Springtime tends to be greener and full of wildflowers too, which makes the whole area just a bit prettier in my opinion. Plus, both seasons are a little less crowded and can bring lower hotel rates than summer. They’re also the most ideal seasons if you plan on biking while you’re up here.
Winter is a totally underrated time of year to visit and still great in my opinion. Many of the hotels will run deals or fun packages during this time of year, it’s less crowded and easier to get reservations, and some wineries (like Flowers) have very cozy indoor tasting rooms that are perfect for cold days.
