Best Healdsburg Getaway
Looking for a casual yet luxurious getaway near San Francisco? Look no further than Healdsburg, a 2-hour drive North of the city. The region boasts low-key, yet highly sophisticated wineries, world-class restaurants, with many other outdoor activities and things to do.
What we like
Pinot noir and zinfandel, friendly wine makers, casual luxury, world-class restaurants
What to keep in mind
Dinners and wineries require reservations well in advance, limited taxi services after 8PM
Similar to most newcomers to the city, my first forays into wine country culture landed me in Napa Valley, along with the 4.5 million other visitors each year who frequent the various replicas of 18th century french chateaus or modern prismatic bunkers carved into the hillside landscape. Party bus to party van, I would file out of the vehicle with 25 of my closest friends, find myself corralled into a group tasting area, and ignore the sommelier while I drank what I most likely could have found in a grocery store - fluttering around the property taking pictures of the barrels, architecture and the views.
Heading back to the city on the same day, the group would be tired and drunk, feeling more beaten down than rejuvenated. For those who love these weekends: drinking exorbitantly amongst the grand and very popular locations, enjoy the raucous times, as I have enjoyed them too. However, now I want to taste good wines, enjoy a more casual ambiance, and spend time with winemakers who can interact more like winemakers than crowd control.
My first time in Healdsburg was in 2017. Edwin and I had friends visiting from Nashville and wanted to show them more than San Francisco. Rather than Napa, this time we opted for Healdsburg, where Edwin had been years before. It would be my first time going to wine country in something other than a party vehicle.
The weekend was the perfect pace to enjoy catching up, learning about wine, eating our hearts out, and relaxing in the casual yet upscale elegance of each establishment. Healdsburg has become a quarterly event for us, and one of our favorite local destinations in the Bay Area. We look forward to sharing our recommendations and tips for the perfect few days in Healdsburg.
Perfect weekend getaway
TL;DR: pick your accommodations, 2 dinner reservations (Day 1 & 2), 2 lunch reservations (Day 2 & 3), and 3 wineries from our list
Staying two nights in Healdsburg, as a weekend getaway from the city, is ideal. Finish up work as soon as possible on Friday, hop in your car and drive up. With Friday traffic, the drive may extend up to 2.5 hours. This will allow you to check in to your accommodations, open a bottle of wine to settle in, enjoy an 8PM dinner reservation, then fall asleep inebriated and happy, excited for the festivities the next day.
On your second day, choose a max of 3 wineries and 1 lunch location; anything more and you will feel too rushed and perhaps a bit too tipsy! Generally, we will either combine lunch to-go and eat at the second winery, or we will start with a tasting room in Healdsburg Plaza and do a sit-down lunch reservation closeby, to save on time. Wineries tend to open between 10AM and 11AM, and then start to close down around 4PM. Cap off the day with dinner around 7PM, after a cat nap or glass of wine back at your accommodations.
Check-out from your hotel on your third day. With brunch (or lunch) reservations in Healdsburg Plaza take some time to roam around, exploring the shops, art galleries and people. Keep an eye on the fountain in the middle of the square, as we have seen many children fall in, either accidentally or on purpose: 5 points if you catch a glimpse! Thereafter, head back to the city, relaxed, happy, and looking forward to when you will return - I am sure there will be a wine club pick-up next quarter.
Relaxing add-on to a longer bay area trip
TL;DR: pick your accommodations, 3 Healdsburg dinner reservations (Day 1, 2 & 3), 3 Healdsburg lunch reservations (Day 2, 3 & 4), 3 wineries, and a plan for your additional full day in the area
For those coming from afar, stay three nights in Healdsburg. Similar to the previous itinerary, Day 1 would include transport up to Healdsburg with a dinner reservation in Healdsburg Plaza. If you make a day of driving up from San Francisco to Healdsburg, stop off at the Golden Gate Viewpoint, hike to Stinson Beach, and then grab a late lunch at The Barlow in Sebastopol.
Day 2 is the same as the previous itinerary. However, on Day 3, consider something that the broader region has to offer. From a mud bath in Calistoga to floating down the lazy Russian River, there are many fun and unique experiences within an hour drive of Healdsburg.
Check-out from your hotel on Day 4, lapping up the last bits of this trip - hoping to return again.
Dinners in Healdsburg
Dinner prices in this section consider food and a few cocktails or wine.
Pastas on point, Bib Gourmand, $90 to $100, Website
Chalkboard is my personal favorite dinner restaurant in Healdsburg. While located in one of the most up-scale hotels, the Hotel Les Mars, Chalkboard stays true to the region's casual atmosphere, while still promising world-class dishes. Executive Chef Justin Davis's family-style sharing menu of locally sourced small plates that tantalizes the taste buds is ever-changing, and will always send me home festively plump and happy. Count on fun appetizers, the most flavorful pastas, roasted and grilled meats for mains, with fun desserts and unique ice creams to top off the experience. Reservations can be made on OpenTable up to 3 months in advance.
California-style small plates, One Michelin Star, $110 to $120, Website
A newly minted Michelin-starred restaurant in 2021, the farm-to-table Barndiva is as much fun as it is delicious. The dinner menu, from Erik Anderson is dubbed as modern country cuisine. Dishes can be shared family-style or eaten individually, with choices such as goat cheese croquettes, hamachi crudo, beet and maple risotto, pan seared hokkaido scallops, or maple leaf duck breast. Seating may be inside the renovated barn, outside on the patio, or in their garden orchard. Don’t forget to sneak a peek at the garden annex next door. Reservations can be made on OpenTable up to 30 days in advance.
Best scallops in Healdsburg, Michelin Guide, $120 to $200, Website
Valette is a welcoming establishment right in Healdsburg Plaza. At some point during your meal, you might even be greeted by the owners’ father, sipping a glass of red wine and making sure your meal is up to snuff. The Michelin-guide contemporary American restaurant provides guests with high quality, yet simple dishes, that showcase the region’s farmers and other producers. Valette is always in our rotation of must-eat places, due to the Day Boat Scallops en Croute - think scallops cooked in a puff pastry with dried squid ink on top. (Look for the video in our Instagram post!) Chef Dustin Valette also offers a five-course tasting menu (~$90 per person) with the optional wine pairing (~$60 per person). Reservations can be made on OpenTable up to 6 months in advance.
Dry Creek Kitchen
Sophisticated, Michelin Guide, $150 to $160, Website
Dry Creek Kitchen, a Charlie Palmer establishment, offers either an a la carte experience or a seasonal three- or five-course prix fixe menu showcasing up-scale California cuisine. Either experience is not conducive to family-style sharing, and each guest should order their own entree. The Michelin-guide restaurant maintains the Charlie Palmer level of quality, with Chef Wyatt Keith presenting fine-dining dishes with premium ingredients. While we always enjoy the dishes at Dry Creek Kitchen, the ambience is more buttoned-up. As such, this may not be the restaurant for you if your group tends to be louder after a day of drinking. However, bring your parents, they will love it! Reservations can be made on OpenTable up to 6 months in advance.
Backup, $100 to $110, Website
Spoonbar at the h2Hotel, serves up good farm-to-table California cuisine, with cocktails that focus on locally sourced ingredients, including the spirits. Dine in the airy lobby of the h2Hotel or outside in the garden. Great for a last minute trip to Healdsburg, this restaurant almost always has reservations available, which may be made on OpenTable up to 3 months in advance.
New addition, $90 to $100, Website
As the newest addition to our list of recommendations, we are excited to try The Matheson on our next trip to Healdsburg. Opened by Valette’s Chef, The Matheson is a restaurant, sushi kitchen and wine lounge, including a ‘wine wall’, featuring 88 wines on tap, allowing guests a wine tasting experience without the need to commit to a full glass of any one wine. Reservations can be made on OpenTable up to 2 months in advance.
Once in a lifetime, Three Michelin Stars, $825 to $1,400, Website
What can we say about the three-Michelin starred restaurant SingleThread, other than it is a delicious once-in-a-lifetime experience. Guests are treated to a 10-course tasting menu ($425 to $495 per person), showcasing the seasonal produce from Chef Kyle Connaughton and Farmer Katina Connaughton’s local farm. A wine pairing, which includes a separate wine for each course, is also available at three price points ($195, $300, and $500 per person). Sometimes there is an eleventh course available at an additional cost.
A great find for our pescatarian friends, the menu from the couple is Japanese inspired with many sashimi elements throughout. If you are a pescatarian or eat all the meats, get ready, buckle up for this amazing, yet very long, culinary experience! Reservations for SingleThread are released on Tock at 9am PST on the 1st of every month, for the upcoming month.
Brunch or Lunch in Healdsburg
Prices in this section consider food and nonalcoholic drinks-only.
Bravas Bar de Tapas
Tapas and cocktails, $40 to $60, Website
If you are looking for a sit-down lunch with creative cocktails, stop into Bravas Bar de Tapas, owned by James Beard Outstanding Restaurateur semifinalists Mark and Terri Stark. Aptly named, this is a family-style tapas restaurant. Croquetas are always my favorite and the eggplant chips with honey and rosemary are a must, but everything on the menu is delightful. The back patio is a relaxing and enjoyable location for eating outside when the weather is nice. If you are on a tight schedule, let your server know at the beginning, so they may course your order to your liking. Reservations can be made on OpenTable up to 3 months in advance.
Standard American brunch, $30 to $45, Website
A brunch-focused menu (not lunch) is served on the weekends at Barndiva. Unlike its dinner option, Barndiva’s brunch menu is not family-style, and I often have trouble deciding on just one entree to order. The menu includes a black truffle croque monsieur, fried chicken sandwich, or goat cheese croquettes - all with Barndiva’s Michelin-starred twist. Reservations can be made on OpenTable up to 30 days in advance.
Dry Creek General Store
Sandwiches to-go, $20 to $35, Website
One of our time-saving tips is to wine and dine. Grab sandwiches at the well-known Dry Creek General Store, and eat in the picnic area at Dry Creek Vineyard, across the street, while you sip the many Zinfandels available.
If you have hired a driver, provide them your order in the morning. They can call it in and pick it up before you are done with the first tasting. Dry Creek General Store offers drivers a free sandwich for their hassle.
If you are not using a driver for the day, save time by ordering in advance. Sandwiches are made before the lunch rush, so plan to pick up your sandwiches as close to lunchtime as possible, or your food may be sitting in the bags for longer than you might like.
Roof 106 (@ The Matheson)
Lunch with a view of Healdsburg Plaza, $40 to $60, Website
Situated on the rooftop of The Matheson, Roof 106 is the restaurant's up-scale cocktail lounge and lunch area, with views of Healdsburg Plaza. There are no reservations required for lunch, but plan to arrive 10 minutes before it opens at noon to jump in line. When we dined at Roof 106 in October, right after the rooftop opened, we arrived 5 minutes to noon, and were the second group in the queue, which quickly grew behind us. Menu items include charcuterie, pizza, and various piadines.
Costeaux French Bakery
Bakery-style brunch, $20 to $35, Website
The most relaxed brunch on our list, Costeaux is both a walk-up bakery with a large assortment of pastries for a quick morning bite, as well as a sit-down restaurant for something more relaxing. The menu contains a deep dish quiche, monte cristo, breakfast sandwich, and omelets, that all can be topped off with french toast made with the bakery’s signature cinnamon walnut bread. If you fill up too fast, we enjoy buying a loaf of cinnamon walnut bread and making your own french toast at home or at your accommodations the next morning.
Costeaux does not take reservations. For couples, there shouldn’t be a long wait as a walk-up. For groups of 4 or more, call ahead to ask for the wait time, and send one person in the party to the restaurant to jump on the waitlist based on your call.
Opening Soon, Website
We can’t wait to try Little Saint, housed in the old Shed, when it opens in February 2022!
Wineries in Healdsburg
Reservations are required at all wineries included in our list, and highly recommended or required for almost all other Healdsburg wineries.
Foppiano Vineyards and Winery
Down to earth winery with ample space for groups, $25 per tasting, $15 to $60 a bottle, Website
A go-to winery, Foppiano has been making wine since 1896 and maintains a wide array of different varietals, such as petite sirah, pinot noir, zinfandel, sauvignon blanc and chardonnay. With varying price points, this winery appeals to many different types of visitors, from those with an eye towards exclusivity to those who want the best value.
Set in and around the old estate home, tastings occur inside the casual tasting room, or outside on picnic tables with views of the vineyards running down to the river’s edge. Our favorite bottles include the Grant Station Carignane and the River’s Edge Pinot Noir (both $48 per bottle).
Notable Club Member Perks: 10% off purchases, complimentary tastings of up to 4 guests
Ridge Vineyards - Lytton Springs
One of the wineries that started it all, $30 per tasting, $20 per tasting, $30 to $367 a bottle, Website
A well-known winemaker, Ridge focuses on an old world style of wine, using a majority of aged vines (older than 50 years) across their portfolio. Old vines create deep roots in the soil and a more complex flavor profile than traditional modern vineyards. While many Ridge wines are sourced across California, Ridge contracts sustainably with vineyards that focus on growing according to their level of sustainability and care.
The tasting room, patio, and main building composed of naturally cooling, clay-covered straw bales is surrounded by 115-year-old vines. Beyond the legend of the Monte Bello, our favorite go-to bottle is the Ponzo Zinfandel ($35 per bottle). Additionally, the Lytton Springs Zinfandel ($45 per bottle), grown, harvested, fermented, and aged on property, is also delightful.
For those wanting to tour a vineyard in Healdsburg, we enjoyed the Ridge Century Tour and Library Tasting ($50 per person) and added on the sizable charcuterie platter ($50). When we brought our parents here for the tour, we learned about the old vines, history of the company, distillation and barreling process, with a seated wine tasting in a private room at the end. Laurie kept us entertained with her fun quirkiness and informative dialogue.
Notable Club Member Perks: 10% off purchases, complimentary tastings of up to 4 guests, exclusive access to member-only wines
Limerick Lane Cellars
Individual care for each customer, $25 per tasting, $48 to $85 a bottle, Website
Limerick Lane Cellars is THE place to come if you are looking for an exceptional private setting without the pretension you might feel at other establishments offering private tastings. This small hidden gem is less known than others as the vineyard only allows one tasting group at a time. Expect personalized interactions, while drinking great wine. Limerick Lane is also one of the few wineries to make a white and rosé crisp and dry enough for us to really enjoy (Riesling - $36 and Rosé - $28). Our favorite bottle of red wine is the Zinfandel Block 1910 ($62 per bottle).
Notable Club Member Perks: Complimentary tastings of up to 6 guests, complimentary shipping on orders of 6 bottle or more
Dry Creek Vineyard
Affordable zinfandel and a picnic, $25 per tasting, $16 to $90 a bottle, Website
The most approachable winery on our list, Dry Creek Vineyard offers pristine grounds, including an insectary garden, set against a Loire Valley-inspired chateau. If you are looking for the photo opportunity of Napa, with the ambiance and service of Healdsburg, visit Dry Creek Vineyard. With picnic tables and other group setups, tastings are provided to guests in their tasting room or the expansive grove outside of the chateau. This winery is perfect for combining lunch and a wine tasting by picking up sandwiches at Dry Creek General Store beforehand. Our favorite bottle is the Meritage ($65 per bottle).
Notable Club Member Perks: 20%-25% off purchases, complimentary tastings of up to 6 guests
Banshee Tasting Room
Stock up on your Halloween-themed wine bottles, $40 per tasting, $22 to $70 a bottle, Website
On the more recent side of winemaking, Banshee was created in 2009 in the Dogpatch neighborhood of San Francisco, and opened this tasting room in 2013. The winery strives to make a variety of complex and delicious wines that are affordable to the average consumer. The tasting room is a cozy spot just off of Healdsburg Plaza that boasts eclectic decorations and a friendly hip atmosphere. A go-to spot when pairing with Bravas Bar de Tapas thereafter, directly across the street. Our favorite bottle is the Tina Marie Pinot Noir ($60 per bottle).
Notable Club Member Perks: 10%-20% off purchases, complimentary tastings of up to 4 guests
Siduri Tasting Lounge
So many fun pinot noirs - but not your Safeway Sudiri, $30 per tasting, $25 to $70 a bottle, Website
The Siduri Wine Tasting Lounge is just downstairs from Two Thirty-five Luxury Suites, perfect for starting your day by mozying just one floor below. The winery specializes in cool-climate pinot noirs across the West Coast - from Willamette Valley, Oregon to Santa Barbara, California. Their mission is to highlight the uniqueness of each region in every wine, and they succeed at this. Not to be confused with the bottles found in Safeway and Albertsons, the exclusive tasting room wines span from light to bold and spicy to earthy. The staff are knowledgeable on every aspect of each flavor profile, but the ambience is geared more towards learned pinot connoisseurs. Our favorite bottles are the Gran Moraine and Clos Pepe Pinot Noirs (both $59 per bottle).
Notable Club Member Perks: 20% off purchases, complimentary tastings
Francis Ford Coppola Winery
The most famous winery in the area, $30 per tasting, $8 to $120 a bottle, Website
One of the most well-known wineries in the area, due to the famous owner of the same name, this tasting room boasts 40 wines that are produced on-site. The property also includes a restaurant and pool area, surrounded by a sustainably farmed vineyard. This is the most commercialized experience, but if you are wanting to see where those wines you can buy at home are produced, please stop by and enjoy! Our favorite bottle is the Director’s Cut Zinfandel ($25 per bottle).
Notable Club Member Perks: 25% off purchases, complimentary tastings of up to 4 guests, early access for pool reservations
32 Winds Tasting Room
Visiting your rich aunt’s country estate, $45 per tasting, $26 to $75 a bottle, Website
The property is well-kept with an indoor and outdoor seating area. We have visited 32 winds two times, and were hosted by Sherry, head of customer relations: her personality is welcoming as if she is your fun furbaby-loving aunt that you are visiting for the afternoon. Stories and laughs abound.
To thoroughly enjoy this tasting experience, visit with a wine club member. For club members, the property is dog friendly and outside food and drink is permitted. In addition, the $45 per person tasting fee is steep, and not waived, unless visiting with a club member.
Notable Club Member Perks: 15%-20% off purchases, 2 complimentary tastings of up to 4 guests annually, catered lunch option from local chefs available with wine tastings
Where to Stay in Healdsburg
We enjoy sharing a perfect weekend getaway with friends, and tend to make Healdsburg a triple date weekend. In that sense, our favorite accommodation is Two Thirty-Five Luxury Suites. Just a half block from Healdsburg Plaza, this property includes 4 luxury suites, with each unit including a living room, dining area, fully equipped kitchen as well as 3 primary bedrooms (spacious king bedrooms and ensuite bathrooms). We love that each set of friends has their own private bedroom, but there is a common area exclusive to our group to relax and enjoy - not needing to worry about finding a common area during downtimes at a hotel. Make sure to book in advance. Due to the property’s limited number of suites, availability can be fleeting.
If you are coming up with fewer in your party, hotels like the Hotel Healdsburg ($578 to $799 per night*), h2hotel ($409 to $609 per night*), Hotel Les Mars ($467 to $700 per night*), and Harmon Guest House ($379 to $619 per night*) are also right on Healdsburg Plaza and offer extreme luxury. (Hotel Les Mars is a member of Relais & Chateaux, the same association of the Wild Coast Tented Lodge, where we stayed while on Safari in Sri Lanka’s Yala National Park.)
For a less expensive accommodation, try Hotel Trio Healdsburg ($270 to $579 per night*), a Marriott property that is a 1-mile walk from Healdsburg Plaza, through the convenient Foss Creek Trail. The distance is close enough to walk, even at night. The property offers a pool area, but don’t get excited about the in-unit kitchens, the grill top and pan quality are not conducive to a well-cooked breakfast or meal.
* Nightly rates represent a standard king bedroom, excluding taxes
Getting around Healdsburg
Wine and driving don’t legally mix, as such, it is important to plan out how you will get from point to point throughout your trip to Healdsburg, in order to stay safe and within the law. Even though we recommend driving yourself to the area from San Francisco, driving your own car should be minimal during the stay.
With accommodations close to Healdsburg Plaza, restaurants will be a couple of steps away. However, planning transportation to each winery may take some thought.
For the most relaxing yet expensive solution, hire a driver! Wine Tour Drivers is a great service. The company provides a driver for your personal vehicle at $50 an hour, excluding tip. We have found our day is 6 to 7 hours long from pickup to drop off with Wine Tour Drivers.
Compared to an estimated total cost of $400 to $450 for a driver, the most economical (but still relaxing) option has been a strategy we have developed over time, minimizing driver costs down to about 2 to 3 taxi rides, with an average cost of $25 per ride:
Start in Healdsburg Square and End Far Away
If you want to sit down for lunch in Healdsburg Plaza, start as early as possible at your first winery in downtown Healdsburg, with lunch at either Bravas Bar de Tapas, Barndiva or Roof 106. Thereafter, taxi to the second winery, third winery and then back home. The two last tastings should be close together, as sitting down for lunch greatly diminishes your available travel time for the day.
Start Far Away and End Far Away
With this strategy, you or multiple drivers in the group drive to the first winery. After, head back to the hotel and walk to a tasting room in Healdsburg Plaza; we enjoy the Banshee Tasting Room or Siduri Tasting Lounge. Pick up a late lunch to-go and taxi to a winery that allows you to eat outside food (Our favorite is sitting at the Foppiano Vineyards and Winery picnic tables while enjoying our order from Bravas Bar de Tapas). Make sure to confirm with the winery beforehand they allow outside food to be eaten on-premise. With this plan, a hearty breakfast before leaving for the day is important, but if you stay at Two Thirty-five Luxury Suites, with its full kitchen, that should be no problem!
Don’t Leave Downtown Healdsburg
Of course there are enough great tasting rooms in and around Healdsburg Plaza, if you don't mind missing the views and meeting the winemakers directly. Just focusing on getting tipsy is totally fine - and on par with many of the locals! - which is why we have heard from many taxi drivers that they stop serving patrons as the sun goes down.
What to Wear
With Healdsburg tending toward the casual side of luxury, visitors do not need to worry too much about what they wear. In the summer or on a hot day, we may go wine tasting in shorts and polo, switching to jeans in the winter. For dinners, throw on a flannel shirt and you will fit right into the crowd. Remember to check the weather before packing, as temperatures vary widely, and hot days may also pop up during winter months.
Other Points of Interest
Russian River Tea Company
Healdsburg Plaza, Website
A stop into this cozy shop is a requirement for both of us on every trip to Healdsburg. The store hosts a multitude of amazing teas, as well as scrumptious treats, including those from the Windsor Toffee Company.
Healdsburg Plaza, Website
Our favorite art gallery in the area, we enjoy contemplating the newly for-sale pieces with our friend Rena, Director of Sales.
Healdsburg Farmers Market
Healdsburg Plaza, Website
Saturdays, 8:30AM to 12PM (April 16 - December 17) - West Plaza Parking Lot
Tuesdays, 9AM to 12:30PM (May 17 - October 25) Healdsburg Plaza
Pop into the Healdsburg Farmers Market, if you are in town on the right day. Vendors include both food stands (flowers, cheeses, honey, olive oil, bread, wild fish, pasture-finished meat, and fresh eggs), as well as art and home decor.
Foss Creek Pathway
Take a morning stroll along the Foss Creek Pathway. While gyms are not prevalent in many Healdsburg hotels, walking is a great way to burn off last night's dinner and yesterday’s wine.
Francis Ford Coppola Pool
10 minutes from Healdsburg, Website
Party at the Francis Ford Coppola pool! If you have time to plan far in advance, reserve a cabana or set of lounge chairs at the winery’s pool area. This highly sought after experience is an elusive booking, but if you do snag a reservation, enjoy this fun pool day in the glorious sun!
25 minutes from Healdsburg, Website
If the Francis Ford Coppola Pool is not your speed, but you are looking for another way to cool off, float down the Russian River in Guerneville. Pick up a six pack of whatever beverage you like, your favorite themed floaty, and hop on in. We recommend dipping in at Steelhead Beach and finishing up at Sunset Beach. Don’t miss your exit, as there are not many easy egress opportunities past Sunset Beach!
Depending on the speed of the river, this float may take between 6 and 8 hours. Make sure to park a car at Sunset Beach to facilitate a way back out of the area. If you only have one car, Ubers/Lyfts are generally available, but not prevalent. Stash your car at Sunset Beach and then Uber/Lyft back to Steelhead, so that you are not worried about transportation while tired and ready to go back to your accommodations.
40 minutes from Healdsburg, Website
East of Healdsburg is Calistoga. With its geothermal activity, Calistoga is known for rustic spa retreats and relaxation. A unique experience is a couple’s mud bath paired with soaking time in a mineral pool. Start your morning with a couple’s hot air balloon ride ($2,200 per couple), visit the Old Faithful Geyser, enjoy lunch at Evangeline, sip and shop in downtown Calistoga, spend some time relaxing in a mud bath, then head back to Healdsburg for a late dinner.
1 hour from Healdsburg, Website
If wine tasting is your passion, and you would like to continue the best Healdsburg getaway adventure with a second full day of wine tasting, consider heading to the city of Sonoma. Sonoma Plaza and the surrounding area hosts plenty more wineries and tasting rooms. For lunch, make a reservation at the El Dorado Kitchen.