Exploring Healdsburg, California Wine Country's Best Kept Secret
Food & Wine
Healdsburg is the hidden gem of Sonoma County, with many incredible vineyards and a fabulous town square lined with restaurants and tasting rooms. Typically, wineries here have more availability and often have special meal and tasting menu pairings. The town and surrounding areas are also stunningly green. There is a strong eco-focus put forth by every hotel in the area to preserve the natural beauty of wine country. At night, you can sip wine and make s'mores on one of the many rooftop lounges in town while stargazing.
The Fora Difference
Book with Lindsay to access exclusive perks and experiences on your trip.
Free upgrades, spa credits and more—we got you
Customized travel planning for your style
Expert advice from people who’ve actually been there
Where to stay
Nestled amongst the rolling hills of Sonoma Valley, Montage is an authentic hotel with a spa, zero-edge resort pool and three signature dining options.
$100 hotel / resort credit.
Upgrade & extended check-in/out whenever possible.
Harmon Guest House
The Harmon Guest House is a modern style hotel with cutting-edge architecture for the contemporary traveler.
$50 hotel / resort credit.
Welcome treat in room on arrival.
Upgrade based upon availability.
A charming Wine Country hotel with an adorable porch and leafy pathways across the property.
$25 hotel / resort credit.
Welcome treat on arrival.
Upgrade & guaranteed 1pm check-out.
Unlock perks by contacting Lindsay to book your trip.
Day 1: Arrive & Check Out Town
Watch Sunset & Sip Wine
Arrive in Healdsburg around 5pm (by car from any bay area city/airport or by flying directly into Santa Rosa STS) so that you have time to settle into your room and change for the evening. Head over to Scout Field Bar in the hotel lobby for a perfect view of sunset and some incredible cocktails.
Dinner in the Square
After drinks, take a complimentary shuttle downtown for dinner at Bravas. After dinner, walk over to the Matheson for wine, dessert or just a nice view. The square is adorably lit at night, so feel free to walk around and enjoy the evening.
Day 2: Wine Country Day
Wake up early and head over to the bike center to begin your complimentary archery lesson! The guides are incredibly patient and helpful; you can have up to 4 people shooting at one time. After your lesson, head back to the room and get ready for a big day of wine tasting!
Head to Robert Young Estate Winery for an 11 am tasting reservation. Pricing varies but this location is quite reasonable and will comp a tasting if you buy any wine. They have a lovely outdoor tasting room too.
Next, head to Willi's | Seafood & Raw Bar for a 1 pm lunch. Everything is incredibly fresh and there are lots of options for non-fish eaters.
Wrap up a day of vineyards with one of the most scenic in the area: Ridge Vineyards. Head in for a 3:30 pm tasting and enjoy your secluded, comfy couch as you look out across the vines before heading back to the hotel.
Under the Stars
Give yourself time to relax and freshen up before a phenomenal dinner at Hazel Hill, the onsite restaurant of the Montage. This coursed menu will run about $150 per person, or $200 with wine pairings. They are very accommodating to any dietary restriction and are also happy to substitute seasonal flavors for traditional menu items at your request.
Finally, wrap up the night with some star gazing, a unique experience hosted by the Montage. You'll go from the restaurant, past the lobby and into the entrance to the vineyards (or ask the concierge for guidance) to find an elderly gentleman and his daughter polishing their 5' brass and gold telescope. They will guide you along various constellations, teach you about some of the stories behind the stars and allow you to view space through their telescope.
Day 3: Brunch & Relaxation
Wine & Brunch
Wake up at your leisure and head to Capo Creek, an incredible boutique winery and restaurant. You'll have a 2-hour brunch tasting menu paired with wines and hear about the life story of Mary, the owner, and her many dogs.
After brunch, head back to the hotel and take advantage of the pool, spa and other amazing hotel amenities. You can also explore the expansive property by foot or golf cart to see the spaces deep in the vineyards.
For dinner on your final night, head into town using the hotel's shuttle service. For something more low-key, make a reservation at The Taste of Tea, a charming tea shop and restaurant. If you want to have a more upscale experience, visit Harmon Guest House's rooftop.
Need to Know
Looking for more travel inspo? Check out my guide The Best of Puerto Vallarta, Mexico.
Get in touch with Lindsay
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Lindsay within a business day or so. You'll also be subscribed to our travel newsletter (you can unsubscribe at any time).