Welcome to a Wine Weekend in Healdsburg, California, your go-to guide on how to plan the perfect trip to Healdsburg wine country! In this post, I’ll share what you need to know about visiting Healdsburg including how to get there, top-rated accommodations, what to do, where to eat, and my exact itinerary.

Whether you’re a travel enthusiast, a couple on a romantic escape, or a devoted wine lover, this guide will have you covered on how to plan your perfect weekend in Healdsburg.

Getting to Healdsburg / How to Get Around

Nestled in the heart of Sonoma County, Healdsburg is conveniently accessible by car from major Bay Area cities.

• Rent a Car: Enjoy a scenic drive along rolling hills and vineyards. Renting a car is ideal if you wish to explore the countryside at your own pace.
• Local Transport: Once you’re in town, you explore Healdsburg’s charming downtown on foot, bike, or short drive via Uber/Lyft/Taxi.
• Shuttle Services: Some hotels provide shuttle services to local attractions and wineries.

We flew into Oakland Airport, quickly rented a car, and took the 1-hour and 45-minute drive up.

Best Places to Stay

• Montage Healdsburg: Experience luxury like no other with upscale amenities, personalized service, and the unique perk of a golf cart ride to your vineyard-view room.
• Hotel Healdsburg: A boutique option that offers modern comforts combined with local charm, perfectly situated near downtown attractions.
• Healdsburg Inn, A Four Sisters Inn: Enjoy the historic ambiance and central location, ideal for those who want to explore the town on foot.
• H2Hotel: Another boutique option in the heart of downtown with a spacious pool and room balconies.

For those wanting a taste of luxury, Montage Healdsburg provides an unforgettable stay – and this is where we stayed. At the time of writing, Montage Healdsburg currently offers a buy 2-nights and get the 3rd night free, which we took advantage of over a holiday weekend.

The Montage also includes complimentary tastings for a dozen or so wineries in the area they partner with, which I’ll cover below 🙂

We were greeted with a warm welcome and wine, of course, followed by a golf cart ride to our room. And speaking of the room…just wow. Spacious, luxurious, and cozy with a large two-person bath tub, a balcony over looking their own exclusive vineyard, and a fire-pit to top it all off.

Best Things to Do

Wine Tasting

There’s no shortage of incredible wineries in Healdsburg, and while I love the Napa region as well, Healdsburg’s vibe is much more laid-back with just as acclaimed wines.

Through the Montage, we enjoyed two complimentary tastings at MacRostie Winery and Lambert Bridge Winery, and while complimentary, the service was above and beyond.

Our first stop was MacRostie Winery, well known for their bubbles and pinot noir. Special shoutout to our wine educator, Season, for a warm welcome and an amazing start to our Valentine’s Day! Great views and great wine.

We also visited Lambert Bridge Winery, and were treated to not only amazing wines, but local cheese and chocolate truffles to compliment our tasting. Shoutout to our wine educator, Stefanie, for indulging us in a blind side-by-side!

Lastly, I had been wanting to visit Aperture Cellars for years after tasting their Del Rio Vineyard Cabernet Sauvignon and we were delighted in the wines we were able to try. Thank you to our wine educator, Grant, for making this a memorable experience!

Other Activities

Healdsburg isn’t just about wine—it’s an all-around sensory experience. Check out these other must-do activities:

• Guided Vineyard Tours: Gain insider knowledge with tours that take you through the lush vineyards and production facilities.
• Art & Culture: There are a ton of local art galleries and shops in downtown. Splurge a little!
• Outdoor Activities: Enjoy bike tours, food tours, horseback riding, and many more things to do. Here are some top rated tour groups.

Best Cafes and Restaurants

Just as important as the wine tasting, is the food you enjoy! Over our weekend, we split time between eating downtown and enjoyed the service at The Montage. Here are my favorites and recommendations:

Restaurants

• Journeyman Meat Co: Enjoy a hearty lunch with locally sourced meats and get the truffle chips!
• Baci: Indulge in a gourmet Italian dinner in the heart of downtown, with a local wine pairing.
• Lo & Behold Bar + Kitchen: Savor unique dishes like an incredible Peruvian sandwich during a laid-back lunch experience.
• Bravas Bar de Tapas: Experience creative, vibrant tapas in a lively downtown atmosphere that perfectly wraps up your day.

Wineries

• Knights Bridge: A unique blend of rustic charm and modern sophistication, where scenic vineyard views set the stage for an intimate wine tasting.
• Silver Oak Alexander Valley: Indulge in world-class Cabernet Sauvignon in an elegant tasting room, celebrated for its legacy and breathtaking Alexander Valley vistas.
• Robert Young Estate Winery: This winery offers the chance to taste world-class wines alongside local culinary delights. The views are amazing!

Cafes & Coffee

• Black Oak Coffee Roasters: Kick off your mornings with a perfectly brewed cup of coffee. I always grab a bag for myself and friends to take home!
• Costeaux French Bakery: Treat yourself to artisanal pastries, fresh breads, and baked delights.
• Plank Coffee Healdsburg: Just outside downtown, offering a cozy feel and tasty coffee.

Bars & Breweries

• The Rooftop: Delight in panoramic views paired with a dynamic dining experience that elevates your Healdsburg visit.
• Russian River Brewing Company: Spacious indoor and outdoor brewery with a variety of beer options for all palettes.

Whether you’re mapping out your first visit or returning for another taste of wine country magic, this guide is your gateway to an unforgettable Healdsburg adventure. Experience luxury, flavor, and a hint of local charm!

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